10-583-cr(L)
United States v. Coplan

                                  UNITED STATES COURT OF APPEALS
                                     FOR THE SECOND CIRCUIT

                                             August Term, 2011

(Argued: November 14, 2011                                            Decided: November 29, 2012)

_______________________________________________________________________________

UNITED STATES OF AMERICA,

                    Appellee,

                    v.

ROBERT COPLAN, MARTIN NISSENBAUM,
RICHARD SHAPIRO, BRIAN VAUGHN, CHARLES BOLTON,

                    Defendants-Appellants,

DAVID L. SMITH,

            Defendant.
_______________________________________________________________________________

Before: KEARSE, MCLAUGHLIN, and CABRANES, Circuit Judges.

          Defendants Robert Coplan, Martin Nissenbaum, Richard Shapiro, and Brian Vaughn appeal

from judgments of conviction entered on January 28, 2010 in the United States District Court for

the Southern District of New York (Sidney H. Stein, Judge), following a 10-week jury trial on charges

of conspiracy to defraud the Government, tax evasion, obstruction of the Internal Revenue Service

(“IRS”), and false statements to the IRS. Defendant Charles Bolton appeals from an April 14, 2010

judgment of conviction entered by the District Court following his guilty plea, pursuant to a plea

agreement that contained a limited appeal waiver, to a single conspiracy charge.




                                                    1
       We affirm the convictions of Coplan and Vaughn, reverse the convictions of Shapiro and

Nissenbaum, and vacate and remand the portion of Bolton’s sentence imposing a $3 million fine.

       Judge Kearse dissents in part in a separate opinion.

                                      RICHARD C. TARLOWE, Assistant United States Attorney,
                                           (Mark Lanpher, Andrea L. Surratt, and Katherine Polk
                                           Failla, Assistant United States Attorneys, on the brief), for
                                           Preet Bharara, United States Attorney for the Southern
                                           District of New York, New York, NY, for Appellee
                                           United States of America.

                                      DENNIS P. RIORDAN, (Donald M. Horgan and Gary Dubcoff,
                                          on the brief), Riordan & Horgan, San Francisco, CA;
                                          Ted Sampsell Jones, William Mitchell College of Law,
                                          St. Paul, MN, for Defendant-Appellant Robert Coplan.

                                      NATHAN LEWIN, (Alyza D. Lewin, on the brief), Lewin &
                                          Lewin, LLP, Washington, DC, for Defendant-Appellant
                                          Martin Nissenbaum.

                                      ALEXANDRA A.E. SHAPIRO, (Marc E. Isserles and James
                                          Darrow, on the brief), Macht, Shapiro, Arato & Isserles
                                          LLP, New York, NY; Morvillo, Abramowitz, Grand,
                                          Iason, Anello & Bohrer, P.C., New York, NY, of counsel;
                                          for Defendant-Appellant Richard Shapiro.

                                      ROBERT G. ANDERSON, (Donna Brown Jacobs, on the brief)
                                          Butler, Snow, O’Mara, Stevens & Cannada, PLLC,
                                          Ridgeland, MS, for Defendant-Appellant Brian Vaughn.

                                      MARC N. GARBER, The Garber Law Firm, P.C., Marietta,
                                          GA, for Defendant-Appellant Charles Bolton.

                                      Joshua L. Dratel, Joshua L. Dratel, P.C., New York, NY, for
                                            amicus curiae New York Council of Defense Lawyers;
                                            Laura Grossfield Birger and Rachel B. Kane, Cooley
                                            LLP, New York, NY, for amicus curiae National
                                            Association of Criminal Defense Lawyers; in support of
                                            Defendants-Appellants.




                                                 2
JOSÉ A. CABRANES, Circuit Judge:

         We consider here the fate of four partners and employees of Ernst & Young, LLP (“E&Y”),

one of the largest accounting firms in the world, who appeal their convictions in connection with the

development and defense of five “tax shelters” that were sold or implemented by E&Y between

1999 and 2001. At issue, among other things, is the scope of criminal liability in a conspiracy to

defraud the United States under 18 U.S.C. § 371 and the sufficiency of the evidence with respect to

the criminal intent of certain defendants.

         The defendants in these consolidated actions are three tax attorneys, Robert Coplan, Martin

Nissenbaum, and Richard Shapiro, and one accountant, Brian Vaughn, formerly employed by E&Y.

A fifth defendant, Charles Bolton, was an investment advisor who owned and operated various

asset-management companies.1 Coplan, Nissenbaum, Shapiro, and Vaughn (jointly, the “trial

defendants”) appeal from separate judgments of conviction entered by the United States District

Court for the Southern District of New York (Sidney H. Stein, Judge) on February 17, 2010,

following a 10-week jury trial on charges of conspiracy to defraud the Government, tax evasion,

obstruction of the Internal Revenue Service (“IRS”), and false statements to the IRS. Bolton

appeals from a judgment of conviction entered by the District Court on April 14, 2010, following his

plea of guilty to a single conspiracy charge.2

         For the reasons that follow, we reverse the convictions of Shapiro and Nissenbaum on

Counts One, Two, and Three, and the conviction of Nissenbaum on Count Four, and we affirm the

convictions of Coplan and Vaughn in their entirety. We affirm the District Court’s order sentencing


1 David Smith, the sixth defendant charged in this case, was a fugitive at the time of trial and is not a party to this

appeal.
2Bolton’s plea agreement contained a limited appeal waiver that permitted him to appeal any sentence exceeding six
months of imprisonment based on the application of U.S.S.G. § 2T1.9. Because Bolton’s sentence exceeded six months
of imprisonment and was based on the application of § 2T1.9, his appeal is properly before us.
                                                          3
Bolton principally to 15 months of imprisonment, but we vacate and remand the portion of the

judgment that imposed a fine of $3 million.

                                                   BACKGROUND

           The evidence underlying the convictions, viewed “in the light most favorable to the

prosecution,” Jackson v. Virginia, 443 U.S. 307, 319 (1979), established the following facts.

                                                         I. Facts

           In 1998, E&Y formed a new group tasked with designing tax strategies, or “tax shelters,”3 to

market to “high net worth” individuals who were seeking to shelter at least $20 million from income

tax liability. Originally called the “VIPER” Group (for “Value Ideas Produce Extraordinary

Results”), the group was renamed “SISG” (for “Strategic Individual Solutions Group”) in 2000.

Coplan, Nissenbaum, Shapiro, and Vaughn were the core members of the VIPER Group/SISG.

The facts of this case principally relate to the design, implementation, and audit defense of four tax

shelters developed by the VIPER Group/SISG: the (1) Contingent Deferred Swap (“CDS”); (2)

Currency Options Bring Reward Alternatives (“COBRA”); (3) CDS Add-On (“Add-On”); and (4)

Personal Investment Corporation (“PICO”) shelters. Coplan, Nissenbaum, and Shapiro also

personally invested in a fifth tax shelter, known as the “E&Y 11 Transaction” or “Tradehill,” which

was not marketed to E&Y clients. Although the IRS audited all five tax shelters, only the Add-On

shelter was later subject to tax evasion charges. With respect to the other four tax shelters, the

charged conduct principally relates to alleged false or misleading statements made by the defendants


3   As the jury was instructed:

           [T]he term “tax shelter” refers to investments that have the potential for substantial tax savings as
           one of [their] main benefits. Some tax shelters are legal; other tax shelters are not, it all depends on
           the particular facts.

A I: 562–63/490–91.

                                                              4
in connection with the IRS audits, as demonstrated by the defendants’ internal correspondence,

deposition testimony, and written submissions to the IRS.

           Since the details of the tax shelters and the supporting tax law are largely irrelevant on

appeal, we briefly summarize the (necessarily oversimplified) operation of these transactions as

follows.

                                                A. The CDS Shelter

           The CDS shelter was a tax “deferral and conversion” strategy that allowed a taxpayer to

convert ordinary income into long-term capital gains and defer tax liability to the year after the

income was earned. The taxpayer would form a securities trading partnership in which the taxpayer

served as limited partner and another entity served as general partner. The partnership would then

engage in a large volume of short-term trading and invest in an 18-month swap transaction. Because

of the “trader” status of the partnership, swap payments made by the partnership were deducted as

business expenses. If the swap was terminated early (i.e. before maturity), but after 12 months, the

payments received by the partnership were taxed at the (significantly lower) capital gains rate rather

than the ordinary income rate. Treatment of these payments as capital gains depended upon the

“early termination” of the swap, which allowed the payment to be characterized as a “termination

payment” under the applicable regulations.

                                              B. The COBRA Shelter

           The COBRA shelter was a tax “elimination” strategy that involved creating an asset with a

high “basis” for tax purposes, which the taxpayer could then sell and generate a deductible loss. The

taxpayer would create a limited liability company (“LLC”) that would purchase a pair of offsetting

“digital”4 foreign currency options that involved a bet on how a particular foreign currency would


4   “A ‘digital’ option—often referred to as an ‘all-or-nothing’ option—is an option whose payout is fixed as long as the
                                                            5
perform against the U.S. dollar in 30 days. Prior to the maturity of the options, the taxpayer would

contribute the option contracts to an investment partnership. After the options expired, the

investment partnership was liquidated and the taxpayer’s interest in the partnership was transferred

to a Subchapter S corporation (“S corporation”),5 which would sell the assets and realize a

deductible tax loss.

                                               C. The Add-On Shelter

           The Add-On shelter was a tax strategy marketed as a means to defer indefinitely income tax

liability on capital gains, including the capital gains generated in the second year of the CDS strategy.

Like COBRA, Add-On involved the purchase of offsetting digital option pairs, followed by a series

of transactions designed to generate a tax loss. The offsetting options were structured so that there

was a “one-pip” gap6 between their strike prices, so that, in a theoretical “home run” scenario, a

taxpayer could make a multimillion dollar profit. Unlike CDS and COBRA, however, there was no

reasonable possibility of earning a profit from Add-On apart from the “home run” scenario, since

the Add-On fee structure required payments to E&Y and the entity acting as general partner that

exceeded the potential payoff. As a result, Add-On was the sole tax shelter developed by the

defendants that was subject to substantive tax evasion charges.7




spot price exceeds the strike price; that is, the payout does not increase as the difference between the spot price and the
strike price increases.” Gov’t’s Br. 33-34 n.**.
5 A Subchapter S corporation is a corporation that makes a valid election to be taxed under Subchapter S of the Internal

Revenue Code. See 26 U.S.C. §§ 1361–1379. “Subchapter S allows shareholders of qualified corporations to elect a
‘pass-through’ taxation system under which income is subjected to only one level of taxation. The corporation’s profits
pass through directly to its shareholders on a pro rata basis and are reported on the shareholders’ individual tax returns.”
Gitlitz v. C.I.R., 531 U.S. 206, 209 (2001) (internal citations omitted).

6   A “one-pip” gap is the smallest possible “spread” in an option pair.
7See A III: 567/5548 (Government’s summation) (“Now, Counts Two and Three of the indictment charge all four
defendants with tax evasion, but only with respect to the Add-on transaction, and that’s why I have emphasized that the
other shelters are not charged as tax evasion.”).
                                                              6
                                              D. The PICO Shelter

         The PICO shelter was a tax deferral and conversion strategy that involved an investment in

an S corporation with another shareholder. The taxpayer would purchase 20% of the stock of the S

corporation, while another person associated with the Bricolage investment firm (which helped to

implement the transaction) would purchase the remaining 80% interest. The S corporation (also

known as the Personal Investment Corporation, or “PICO”) would then purchase so-called

“straddles,” financial instruments that generated offsetting gains and losses on foreign currencies,

interest rates, or commodities. After building up a sufficient inventory of “losing” bets, the PICO

would buy out the 80% shareholder. Under a tax regulation, the 80% shareholder would be

allocated his share of the gains recognized by the PICO up to the time of redemption, and all the

gains and losses recognized thereafter (i.e. most of the losses) would be allocated to the taxpayer.

After contributing additional assets to the PICO, the taxpayer could then take the desired deduction.

                                            E. The Tradehill Shelter

         Unlike the other four tax shelters, the Tradehill shelter was marketed only to E&Y partners.

After E&Y sold the consulting arm of its business to a French company called Cap Gemini in 2000,

each E&Y partner received an allocation of Cap Gemini stock. Eleven E&Y partners participated in

Tradehill, which was designed to eliminate the tax due on the income they recognized from the Cap

Gemini transaction. Like COBRA and Add-On, Tradehill involved the formation of numerous

corporate entities and the contribution of option pairs from one entity to another.

         We note that similar tax shelters were marketed and sold by other major accounting firms

and law firms as part of a lucrative “tax avoidance” practice that flourished in the late 1990s.8 See



8 Indeed, the record in this case supports an inference that E&Y was not the first to implement the types of tax shelters

at issue. See, e.g., A IV: 114 (internal e-mail noting that “seven major law firms, AA [Arthur Anderson], and KPMG are
                                                           7
generally The Role of Professional Firms in the U.S. Tax Shelter Industry, S. Rep. No. 109-54, at 3 (2005). In

February 2000, the IRS created the Office of Tax Shelter Analysis and subsequently issued a series

of notices directed at “abusive” tax shelters.9 An April 2005 report issued by the Permanent

Subcommittee on Investigations of the Senate Committee on Homeland Security and Governmental

Affairs stated that “[u]nder current law, no single standard defines an abusive tax shelter.” Id. The

report further noted that “[o]ver the past 10 years, Federal statutes and regulations prohibiting illegal

tax shelters have undergone repeated revision to clarify and strengthen them.” Id. Although this

case does not require us to comment on the substance of those revisions, we think it useful to

acknowledge that the law with respect to tax shelters has evolved since E&Y formed the VIPER

Group in 1998.

                                               II. Procedural History

         A federal grand jury returned a sealed indictment on May 22, 2007, and a superseding

indictment on February 19, 2008, charging the defendants in thirteen counts with a wide-ranging

conspiracy to defraud the United States through the development, sale, and implementation of the

E&Y tax shelters. The superseding indictment was redacted to seven counts (the “Redacted

Indictment”) for the trial of Coplan, Nissenbaum, Shapiro, and Vaughn.10




selling the short option strategy”); A II: 92/1086 (client inquiry about whether E&Y offered a tax elimination strategy
similar to that presented by another consulting group).

9 See Partnership―Audit Technique Guide, ch. 9, available at http://www.irs.gov/Businesses/Partnerships/Partnership--

-Audit-Technique-Guide---Chapter-9---Tax-Shelters---The-Disclosure-Regime-(Revised-12-2007) (last visited Nov. 26,
2012).
10 See Appendix A for an overview of the Redacted Indictment and Information. As noted above, David Smith was
also charged in the Superseding Indictment, but was a fugitive at the time of trial.

                                                          8
            Count One of the Redacted Indictment charged each trial defendant with a conspiracy, in

violation of 18 U.S.C. § 371,11 with three objectives: (1) to defraud the United States by impairing

the lawful governmental functions of the IRS (known as a “Klein conspiracy,” see United States v. Klein,

247 F.2d 908, 915 (2d Cir. 1957)); (2) to commit tax evasion in connection with the Add-On tax

shelter, in violation of 26 U.S.C. § 7201;12 and (3) to make false statements to the IRS, in violation of

18 U.S.C. § 1001.13

            Counts Two and Three charged each trial defendant with tax evasion, in violation of

26 U.S.C. § 7201, in connection with the Add-On tax shelter.

            Counts Four and Five charged Nissenbaum and Coplan, respectively, with obstructing the

IRS, in violation of 26 U.S.C. § 7212.14




11Section 371 provides, in relevant part, that “[i]f two or more persons conspire either to commit any offense against
the United States, or to defraud the United States, or any agency thereof in any manner or for any purpose, and one or
more of such persons do any act to effect the object of the conspiracy, each shall be fined under this title or imprisoned
not more than five years, or both.” 18 U.S.C. § 371.

12 Section 7201 provides, in relevant part, that “[a]ny person who willfully attempts in any manner to evade or defeat any
tax imposed by this title or the payment thereof shall, in addition to other penalties provided by law, be guilty of a
felony.” 26 U.S.C. § 7201.

13   18 U.S.C. § 1001(a) provides, in relevant part:

            (a) Except as otherwise provided in this section, whoever, in any matter within the jurisdiction of
            the executive, legislative, or judicial branch of the Government of the United States, knowingly
            and willfully—

                     (1) falsifies, conceals, or covers up by any trick, scheme, or device a material fact;
                     (2) makes any materially false, fictitious, or fraudulent statement or representation; or
                     (3) makes or uses any false writing or document knowing the same to contain any materially false,
                     fictitious, or fraudulent statement or entry;

            shall be fined under this title, imprisoned not more than 5 years . . . or both.

18 U.S.C. § 1001(a).

14 Section 7212(a) provides, in relevant part, that “[w]hoever corruptly or by force or threats of force . . . obstructs or
impedes, or endeavors to obstruct or impede, the due administration of this title, shall, upon conviction thereof, be
fined not more than $5,000, or imprisoned not more than 3 years, or both.” 26 U.S.C. § 7212(a).
                                                                9
         Counts Six and Seven charged Vaughn and Coplan, respectively, with making false

statements to the IRS, in violation of 18 U.S.C. § 1001.

         Trial commenced on March 3, 2009, with the beginning of jury selection. At trial, the

Government sought to demonstrate that the defendants conspired to conceal the true nature of the

five tax shelters by creating a variety of “cover stories” regarding the purported business purpose of

the shelters, when in fact the shelters were motivated solely by a desire to avoid taxes.15 In essence,

the Government sought to demonstrate that the defendants hid the truth from the IRS by

withholding information and making affirmative misstatements. On May 7, 2009, the jury returned

a general verdict of guilty on all counts. On January 21 and 22, 2010, the District Court sentenced

the trial defendants principally as follows: Coplan was sentenced to 36 months of imprisonment,

three years of supervised release, and a $75,000 fine; Nissenbaum was sentenced to 30 months of

imprisonment, three years of supervised release, and a $100,000 fine; Shapiro was sentenced to 28

months of imprisonment, two years of supervised release, and a $100,000 fine; and Vaughn was

sentenced to 20 months of imprisonment and two years of supervised release. The judgments of

conviction for the trial defendants were entered on January 28, 2010.

         Prior to trial, on January 22, 2009, Bolton pleaded guilty to a Superseding Information

charging him with a single count of conspiracy, in violation of 18 U.S.C. § 371, having three

objectives: (1) to defraud the United States by impeding, impairing, defeating, and obstructing the

lawful governmental functions of the IRS (the so-called “Klein conspiracy”); (2) to make false

statements to the IRS, in violation of 18 U.S.C. § 1001; and (3) to corruptly obstruct and impede the

administration of the internal revenue laws, in violation of 26 U.S.C. § 7212(a). On April 14, 2010,


15The IRS can disallow deductions resulting from a transaction that “can not [sic] with reason be said to have purpose,
substance, or utility apart from [its] anticipated tax consequences. Such transactions are said to lack ‘economic
substance.’” Lee v. Comm’r, 155 F.3d 584, 586 (2d Cir. 1998) (internal quotation marks and citations omitted).
                                                          10
the District Court entered a judgment of conviction sentencing Bolton principally to 15 months of

imprisonment and a $3 million fine.

        The defendants have remained free on bail pending the resolution of this appeal.

                                            DISCUSSION

        The defendants raise no fewer than ten challenges to their respective convictions and

sentences on appeal, which we briefly summarize as follows: (1) the Government’s Klein conspiracy

theory was legally invalid, (2) there was insufficient evidence to support (a) the convictions of

Shapiro and Nissenbaum on Count One, the conspiracy charge, (b) the convictions of Shapiro and

Nissenbaum on Counts Two and Three, the tax evasion charges, and (c) Nissenbaum’s conviction

on Count Four, the obstruction charge, (3) the District Court erred in finding that venue was proper

for Count Six, which charged Vaughn with false statements to the IRS, (4) the District Court erred

by admitting the testimony of alleged coconspirator Graham Taylor, a tax attorney who committed a

variety of crimes involving tax shelters unrelated to this case, (5) the District Court erred in

admitting the out-of-court statements of more than 20 alleged coconspirators, (6) the District Court

erred in excluding portions of Coplan’s and Vaughn’s deposition transcripts, (7) the defendants were

prejudiced by prosecutorial misconduct in the Government’s rebuttal summation, (8) the District

Court erred in (a) declining to give a “theory of the defense” instruction, (b) instructing the jury on a

conscious avoidance theory; and (c) instructing the jury that “economic substance” existed only if

there was a “reasonable possibility” of profit, (9) spillover prejudice infected Coplan’s and Vaughn’s

remaining convictions, and (10) Bolton’s sentence was procedurally and substantively unreasonable.




                                                   11
                       I. Validity of the Government’s Klein Conspiracy Theory

          The first issue on appeal concerns the legal validity of the Government’s Klein conspiracy

theory under the “defraud clause” of 18 U.S.C. § 371.16 As previously noted, Count One of the

Redacted Indictment charged Coplan, Nissenbaum, Shapiro, and Vaughn in a § 371 conspiracy with

three objectives: (1) to defraud the United States (the Klein conspiracy), (2) to evade taxes, and (3) to

make false statements to the IRS. The core objective argued by the Government at trial was the

Klein conspiracy, and that conspiracy forms the primary focus of the defendants’ arguments on

appeal.

                                  A. The Origins of the Klein Conspiracy

          Enacted in 1867, the original federal conspiracy statute was appended to “An Act to amend

existing Laws relating to Internal Revenue and for other Purposes.” Abraham S. Goldstein,

Conspiracy to Defraud the United States, 68 Yale L.J. 405, 418 (1959) (quoting Act of March 2, 1867,

ch. 169, § 30, 14 Stat. 484). In the 1875 codification, the statute was moved from its place among

the internal revenue measures and included among the general penal provisions. Id. at 418 n.36. In

United States v. Hirsch, 100 U.S. 33 (1879), the Supreme Court held that the conspiracy provision was

generally applicable to the whole body of federal law. In so holding, the Court described the

prohibited fraud as “any fraud against [the United States]. It may be against the coin, or consist in

cheating the government of its land or other property.” Id. at 35.

          “It is a well-established rule of construction that where Congress uses terms that have

accumulated settled meaning under . . . the common law, a court must infer, unless the statute

otherwise dictates, that Congress means to incorporate the established meaning of these terms.”


16Section 371 prohibits all conspiracies either “to commit any offense against the United States” (the “offense clause”),
or “to defraud the United States, or any agency thereof in any manner or for any purpose” (the “defraud clause”). 18
U.S.C. § 371.
                                                           12
Neder v. United States, 527 U.S. 1, 21 (1999) (internal quotation marks and alterations omitted)

(omission in the original). At common law, the words “to defraud” meant to deprive another of

property rights by dishonest means.17 See Hammerschmidt v. United States, 265 U.S. 182, 188 (1924);

Porcelli v. United States, 303 F.3d 452, 457 n.1 (2d Cir. 2002) (noting that the “familiar common law

meaning” of the term ‘“fraud”’ involved “using falsity to do the victim out of money or property

interests”). Other federal criminal statutes are generally in accord. See, e.g., United States v. Pierce, 224

F.3d 158, 165 (2d Cir. 2000) (“In the context of mail fraud and wire fraud, the words ‘to defraud’

commonly refer ‘to wronging one in his property rights by dishonest methods or schemes’ . . . .”

(quotation marks omitted)).

         Nonetheless, the word “defraud” in § 371 has been interpreted much more broadly. The

current understanding of “conspiracy to defraud” liability may be traced to two seminal Supreme

Court cases. In the first case, Haas v. Henkel, 216 U.S. 462 (1910), the defendants obtained advance

information from a statistician employed by the Department of Agriculture in order to gain a

speculating advantage in the grain futures market. The Court invoked an expansive reading of the

word “defraud” to bring the defendants’ conduct within the conspiracy statute. Specifically, the

Court held that “it is not essential that such a conspiracy shall contemplate a financial loss or that

one shall result. The statute is broad enough in its terms to include any conspiracy for the purpose

of impairing, obstructing, or defeating the lawful function of any department of government.” Id. at

479.



17 In the authoritative dictionary of the day, “defraud” was defined as “[t]o deprive of right by fraud, deception or

artifice.” The American Dictionary of the English Language 347 (1864). “Fraud” was defined as “[d]eception deliberately
practiced with a view to gaining an unlawful or unfair advantage; artifice by which the right or interest of another is
injured; injurious stratagem; deceit; trick.” Id. at 541. The American Dictionary of the English Language, published by Noah
Webster in 1864, is, of course, not to be confused with the American Heritage Dictionary of the English Language, published
by Houghton Mifflin in 1969, or any modern dictionary bearing the surname of the great American lexicographer.

                                                            13
        Fourteen years later, in Hammerschmidt v. United States, 265 U.S. 182 (1924), the Court

attempted to retrench from the expansive reading of § 371 in Haas. In the words of Professor (later,

Dean) Abraham S. Goldstein of the Yale Law School, “[t]he expansive reading of the statute in Haas

. . . finally led the Supreme Court to attempt a systematic examination of what the judiciary had

wrought. Hammerschmidt v. United States furnished the occasion.” Goldstein, 68 Yale L.J. at 429

(footnote omitted). The Hammerschmidt defendants were convicted of a conspiracy to defraud the

United States by interfering with the World War I military draft through the printing and circulation

of handbills urging those subject to the draft not to obey it. The Supreme Court reversed the

convictions under § 371, holding that “[t]o conspire to defraud the United States means primarily to

cheat the government out of property or money, but it also means to interfere with or obstruct one

of its lawful governmental functions by deceit, craft or trickery, or at least by means that are dishonest.”

Hammerschmidt, 265 U.S. at 188 (emphasis added). Because the defendants’ “open defiance” of the

Selective Service Act was devoid of deceit or other trickery, the Supreme Court held that their

conduct did not fall within the scope of § 371. Id. at 189.

        The Klein conspiracy doctrine at issue here is the progeny of Haas and Hammerschmidt.18 In

United States v. Klein, 247 F.2d 908, 916 (2d Cir. 1957), the defendants were charged with tax evasion

and a “defraud conspiracy” in connection with their whiskey selling business. Id. at 915–16. The

district court entered judgments of acquittal on the substantive counts, and the jury convicted on the

remaining § 371 conspiracy count. On appeal, we found sufficient evidence to support the § 371

conspiracy conviction based on twenty “acts of concealment of income,” including false statements

on tax returns and in interrogatory responses. Id. at 915. Relying on Hammerschmidt, we held that


18Indeed, the appellation “Klein conspiracy” is in some sense a misnomer, since the primary holding of Klein is a
quotation from Hammerschmidt.

                                                        14
         [m]ere failure to disclose income would not be sufficient to show the crime charged
         of defrauding the United States under 18 U.S.C. § 371. The statute, however, not
         only includes the cheating of the government out of property or money, but “also
         means to interfere with or obstruct one of its lawful governmental functions by
         deceit, craft or trickery, or at least by means that are dishonest.”

Id. at 916 (quoting Hammerschmidt, 265 U.S. at 188). Thus, in order to prove a Klein conspiracy, the

Government must show “(1) that [the] defendant entered into an agreement (2) to obstruct a lawful

function of the Government (3) by deceitful or dishonest means and (4) at least one overt act in

furtherance of the conspiracy.” United States v. Ballistrea, 101 F.3d 827, 832 (2d Cir. 1996) (alteration

omitted).

                                     B. The Challenge to Klein

         The defendants argue vigorously on appeal that the Klein conspiracy theory is textually

unfounded. The Government’s stare decisis defense of the Klein doctrine lends support to this view,

as it rests entirely on the construction of § 371 in Hammerschmidt.           There is nothing in the

Government’s brief recognizable as statutory interpretation—no discussion of plain meaning,

legislative history, or interpretive canons. Indeed, in all 325 pages of its brief, the Government does

not even quote the text of § 371. The Government thus appears implicitly to concede that the Klein

conspiracy is a common law crime, created by the courts rather than by Congress. That fact alone

warrants considerable judicial skepticism. See United States v. Lanier, 520 U.S. 259, 267 n.6 (1997)

(“Federal crimes are defined by Congress, not the courts . . . .”); see also Rogers v. Tennessee, 532 U.S.

451, 476 (2001) (Scalia, J., dissenting) (“[T]he notion of a common-law crime is utterly anathema

today . . . .”).

         To justify an expansive reading of § 371, courts have occasionally implied that a conspiracy

to defraud the Government is to be read more broadly than a conspiracy to defraud a private person.

See Goldstein, 68 Yale L.J. at 424. Dicta in McNally v. United States, 483 U.S. 350 (1987), for example,

                                                   15
accepted such a distinction. Quoting a decision of the Court of Appeals for the First Circuit, the

Supreme Court stated that “‘[a] statute which . . . has for its object the protection of the individual

property rights of the members of the civic body, is one thing; a statute which has for its object the

protection and welfare of the government alone, which exists for the purpose of administering itself

in the interests of the public, [is] quite another.’” Id. at 359 n.8 (quoting Curley v. United States, 130 F.

1, 7 (1st Cir. 1904) (alterations in original)). But this conclusion appears to rest on a policy

judgment—that, in the nature of things, government interests justify broader protection that the

interests of private parties—rather than on any principle of statutory interpretation.

        Notwithstanding these infirmities in the history and deployment of the statute, it is now well

established that § 371 “is not confined to fraud as that term has been defined in the common law,”

but reaches “‘any conspiracy for the purpose of impairing, obstructing or defeating the lawful

function of any department of Government.’” Dennis v. United States, 384 U.S. 855, 861 (1966)

(quoting Haas, 216 U.S. at 479). Indeed, Coplan (whose counsel “takes the laboring oar” on the

Klein conspiracy issue) “readily concedes that, were the weight of this Circuit’s case law outcome-

determinative in this matter, his challenge to the government’s Klein theory would fail.” Coplan

Reply 3.

        Although the defendants argue forcefully on appeal that we should follow the example of

Skilling v. United States, 130 S. Ct. 2896, 2928 (2010), and “pare” the body of § 371 precedent “down

to its core,” id., such arguments are properly directed to a higher authority. As an intermediate

appellate court, we are bound to follow the dictates of Supreme Court precedents, no matter how

persuasive we find the arguments for breaking loose from the moorings of established judicial

norms by “paring” a statute.



                                                     16
          In sum, because the Klein doctrine derives from and falls within the scope of the law of the

Circuit (itself grounded on long-lived Supreme Court decisions), we reject the defendants’ challenge

to the validity of that theory of criminal liability.

                                        II. The Sufficiency Challenges

          In addition to challenging the legal validity of the Klein conspiracy theory, defendants

Shapiro and Nissenbaum mount a series of sufficiency challenges.19 As a general matter, a

defendant challenging the sufficiency of the evidence that led to his conviction at trial “bears a heavy

burden,” United States v. Heras, 609 F.3d 101, 105 (2d Cir. 2010) (quotation marks omitted), as the

standard of review is “exceedingly deferential,” United States v. Hassan, 578 F.3d 108, 126 (2d Cir.

2008). In evaluating a sufficiency challenge, we “must view the evidence in the light most favorable

to the government, crediting every inference that could have been drawn in the government’s favor,

and deferring to the jury’s assessment of witness credibility and its assessment of the weight of the

evidence.” United States v. Chavez, 549 F.3d 119, 124 (2d Cir. 2008) (internal citations, alterations and

quotation marks omitted)). Although sufficiency review is de novo, United States v. Yannotti, 541 F.3d

112, 120 (2d Cir. 2008), we will uphold the judgments of conviction if “any rational trier of fact

could have found the essential elements of the crime beyond a reasonable doubt,” Jackson, 443 U.S.

at 319.

                           A. Sufficiency of the Evidence Supporting Count One

          Defendants Shapiro and Nissenbaum first challenge the sufficiency of the evidence with

respect to each of the three alleged objectives of the § 371 conspiracy. As previously noted, Count

One of the Redacted Indictment charged the trial defendants in a § 371 conspiracy with three


19Vaughn joins in Shapiro’s argument regarding the insufficiency of the evidence to prove a Klein conspiracy, but raises
no specific sufficiency challenges of his own. Coplan does not raise a sufficiency challenge.

                                                          17
objectives: (1) to defraud the United States (the Klein conspiracy); (2) to evade taxes, in violation of

26 U.S.C. § 7201; and (3) to make false statements to the IRS, in violation of 18 U.S.C. § 1001.

         “To sustain a conspiracy conviction, the Government must present some evidence from

which it can reasonably be inferred that the person charged with conspiracy knew of the existence of

the scheme alleged in the indictment and knowingly joined and participated in it.” United States v.

Rodriguez, 392 F.3d 539, 545 (2d Cir. 2004) (quotation marks omitted). In the context of a

conspiracy conviction, “deference to the jury’s findings is especially important . . . because a

conspiracy by its very nature is a secretive operation, and it is a rare case where all aspects of a

conspiracy can be laid bare in court.” United States v. Rojas, 617 F.3d 669, 674 (2d Cir. 2010)

(quotation marks omitted) (alteration in original). Where, as here, “a jury returns a guilty verdict on

an indictment charging several acts in the conjunctive, . . . the verdict stands if the evidence is

sufficient with respect to any one of the acts charged.” Griffin v. United States, 502 U.S. 46, 56–57

(1991) (quotation marks omitted). For that reason, “the lack of sufficient evidence to support one

of the objects of a multi-object conspiracy [will] not vitiate the conspiracy conviction, where there

[i]s sufficient evidence to support [another] object.” United States v. Pascarella, 84 F.3d 61, 71 (2d Cir.

1996).

         In what follows, we consider the conspiracy evidence against defendants Shapiro and

Nissenbaum, mindful that “[t]he character and effect of a conspiracy are not to be judged by

dismembering it and viewing its separate parts, but only by looking at it as a whole,” Cont’l Ore Co. v.

Union Carbide & Carbon Corp., 370 U.S. 690, 699 (1962) (quotation marks omitted). Nevertheless, for

the sake of clarity and ease of analysis, we examine the evidence with respect to each alleged

objective of the conspiracy in some detail before considering the conspiracy “as a whole.” For the



                                                    18
reasons that follow, we conclude that the evidence with respect to the intent of Shapiro and

Nissenbaum is insufficient to support their convictions on Count One.

                               1. Conspiracy Evidence Against Shapiro

                                   i. Klein Conspiracy Objective

        The centerpiece of the conspiracy case against Shapiro, an E&Y partner and tax lawyer with

nearly four decades’ experience, is the Government’s claim that he “coached” E&Y partner Thomas

Dougherty to lie to the IRS by helping him come up with non-tax explanations for the COBRA

transaction that Shapiro knew were not true. In rebuttal summation, the Government argued that

“[i]f you credit Mr. Dougherty’s testimony, . . . that alone is proof beyond a reasonable doubt on the

conspiracy count at least as to . . . Mr. Shapiro.” On appeal, the Government similarly argues that

Dougherty’s testimony “standing alone . . . would be sufficient to support his conviction on the false

statements object of the conspiracy.” Indeed, variations on the assertion that Shapiro “coached”

Dougherty to lie appear no fewer than four times in the Government’s brief. See Gov’t’s Br. 67,

112, 117, 134.

        But the record with respect to Dougherty’s testimony is considerably more equivocal than in

the Government’s account.

        April 2, 2001 Conference Call. Dougherty testified that in March 2001, he advised Coplan that

the IRS was auditing the WRB Lake transaction20—the first such audit of a COBRA transaction. In

response, Coplan informed Dougherty that Dennis Conlon, an attorney in E&Y’s national tax

practice, would coordinate the audit response. On April 2, 2001, Dougherty participated in a

conference call with Coplan and Conlon that involved a discussion of “ideas that may be presented


20The “WRB Lake” transaction was a COBRA transaction named for the three business partners who executed the
shelter with the assistance of Dougherty.

                                                    19
to the agent for why [the clients] did the steps that they did” in executing the COBRA transaction.

Following the initial conference call, Conlon sent an e-mail indicating that, “I think we need Richard

[Shapiro] at the first meeting,” because “I want to state our case clearly and correctly from the

beginning.”

        April 24, 2001 Conference Call. On April 24, 2001, Dougherty participated in a conference call

with Conlon, Coplan, and Shapiro. According to Dougherty’s contemporaneous notes, Shapiro

raised the topic of the business purpose of the COBRA transaction during the call.

        May 16, 2001 Preparation Meeting. Dougherty testified that on May 16, 2001, “Conlon led [a]

meeting to prepare Richard Shapiro and myself for our meeting the next day with the IRS.” At that

meeting, Conlon coordinated the assignment of discussion topics for the IRS meeting, reviewed the

relevant points of the IRS Information Document Request (“IDR”), and “anticipated . . . questions

that would come up during the IRS meeting.”

        May 17, 2001 IRS Meeting. The following day, Conlon, Dougherty, and Shapiro met with the

IRS to discuss the WRB Lake COBRA transaction. During that meeting, Dougherty falsely

represented that E&Y “mentioned the tax and financial implications of foreign currency

investments” to the clients involved in the WRB Lake transaction, and that the clients “became

interested” in the COBRA transaction as a result. Dougherty testified at trial that in fact his

discussion of foreign currency investment with the clients was “strictly limited to discussions we had

in the presentation of the COBRA transaction,” and that he had “lied [to the IRS agents] about the

reasons for [the clients] entering into the COBRA transaction.” Although Dougherty testified that

he had told Shapiro “the real facts” about how the WRB clients “had come to Ernst & Young for

the COBRA transaction,” he did not elaborate on the substance of that conversation.



                                                  20
        On these facts, the Government repeatedly asserts that “Dougherty testified specifically that

in consultation with Coplan and Shapiro, he lied to the IRS,” and that “Coplan and Shapiro coached

Dougherty to provide false information to the IRS.” But the record support for these assertions is

slim at best. With respect to the April 24, 2001 conference call, Dougherty’s notes indicate that

Shapiro asked a single question: “What is the business purpose?” During the May 16, 2001

preparation meeting, Conlon—not Shapiro—led the meeting, reviewed the IDR, anticipated

potential IRS questions, and coordinated “who [would] . . . talk about what topics” at the meeting.

Contrary to the Government’s assertion, Dougherty testified on cross-examination that Shapiro

“never told [him] to lie” and did not suggest lying to the IRS in order to conceal “problems” with

the COBRA transaction. Crucially, Dougherty further testified that Shapiro himself “believed

[COBRA] worked under the law.”

        Beyond the Dougherty testimony, the Government also claims that Shapiro engaged in

various acts that, while not “inherently deceptive,” were deceptive “in the context of this case,” as

follows.

           Promotional Materials. The Government faults Shapiro for his participation in E&Y’s policy

of discouraging personnel from leaving PowerPoint slides and other marketing materials with

clients, in case the IRS should demand copies of those materials from the client during an audit. See,

e.g., A V: 42 (Shapiro e-mail stating that presentation materials should not be left with the client).

The Government claims that Shapiro and others enforced this policy to prevent the marketing

materials, which laid out each step of the underlying transactions, from falling into the hands of the

IRS. The Government does not argue, however, that the IRS ever requested copies of the




                                                    21
promotional materials held in E&Y’s own files, or that governing ethical standards required E&Y to

disclose those materials in the absence of such a request.21

         Early Termination. Similarly, the Government highlights Shapiro’s editorial comments on an

internal “Action Plan” that summarized the steps involved in the CDS tax shelter. Shapiro advised

his E&Y colleagues to avoid references to the “early” termination of the CDS swap contracts.22 The

Government characterizes Shapiro’s advice as an “underhanded effort[ ] to protect the descriptions

of CDS that were designed to convince the agents of something the defendants knew to be false.”

Gov’t’s Br. 122 (internal quotation marks omitted). As the Government reluctantly concedes,

however, the CDS swap contracts provided that either party could elect to terminate the swap before

the maturity date—but imposed no obligation to do so. Indeed, several clients inquired about

continuing the swaps to the maturity date because they were “interested in the swap profits,” and

were told that doing so would lead to deferral of income, but not conversion from ordinary to

capital gain. In the end, no CDS swap extended past the early termination date. Although Shapiro’s

edits to the CDS “Action Plan” clearly deemphasized the prevailing expectation of early termination,

it appears that the revised version was in fact more accurate in its summary of the swap contract terms.

          Advice to Keep CDS Trading Account Open. As an additional example of deception “in

context,” the Government points to a suggestion by Coplan, Shapiro, and Nissenbaum that CDS

clients continue trading past the early termination date in order to “mak[e] their tax argument as

strong as possible.” A IV: 214; see id. at 212 (Shapiro e-mail advocating “keeping the trading account

active” in light of the “upside and no down side”); id. at 219. The Government argues that this


21 Cf. ABA Model Rules of Prof’l Conduct, pmbl. ¶ 9 (2006) (reaffirming basic principle of “the lawyer’s obligation

zealously to protect and pursue a client’s legitimate interests, within the bounds of the law”).
22 In the original draft of the CDS Action Plan, Step 45 read as follows: “At the appropriate time during the swap
period, GP will terminate the swaps with the bank.” In response to Shapiro’s advice, Step 45 was edited to read, “Swap
terminates.”
                                                         22
advice “was designed to protect the bogus descriptions of CDS.” Gov’t’s Br. 122. There is no

dispute, however, that the substance of the advice advocated lawful trading activity.

        Review of PICO Documents. Finally, the Government points to Shapiro’s development and

review of various documents related to the PICO tax shelter as evidence of his “involvement in

providing false information directly to the IRS.” Gov’t’s Br. 135. For example, the Government

highlights Shapiro’s involvement in drafting the PICO opinion letter with outside counsel, Peter

Cinquegrani, who was then special counsel at Arnold & Porter. The Government argues, inter alia,

that the opinion letter contained misleading statements because it described PICO as an

“opportunity to create personal investment companies,” A V: 504, when the “real reason” for the

transaction “was to provide tax losses for investors,” A III: 114/3756. Cinquegrani, the self-

described “principal wordsmith” of the opinion letter, testified at trial that he intended the opinion

letter to be misleading because his “intention was to describe the transaction as much as possible as

an ordinary business deal and to downplay all the tax aspects.” There is little such evidence with

respect to Shapiro’s intent. The record of communication between Cinquegrani and Shapiro reflects

a sometimes tense working relationship, in which Shapiro repeatedly raised questions and concerns

about the language of the draft opinion. See A III: 144/3873–145/3876 (Cinquegrani testimony

describing Shapiro as “a pain” and “high maintenance” because he “would frequently ask the same

questions multiple times” and “would revisit the same issues that had previously been addressed”).

For example, Shapiro expressed “concern” that “the nature of the rep[resentation]s investors are

making . . . may be too strong.” A IV: 455. On several occasions, Shapiro proposed revisions that

Cinquegrani incorporated into PICO documents. As a result, an early representation that PICO

clients had a “principal” investment purpose was replaced by a representation that PICO clients had

a “substantial nontax business purpose.” A III: 165/ 3955–56. Shapiro also questioned a draft

                                                  23
version of the opinion letter that inaccurately suggested that the tax consequences of the PICO

transaction were not discussed with clients. A IV: 457. As a result, the final opinion letter disclosed

that potential PICO investors were “provided an overview of the economics of the trading strategy,

including potential tax consequences.” A V: 575.

        The Government argues strenuously on appeal that the final opinion letter still contained lies

and misleading statements about the “real reason” for the PICO transaction. But we note that, as

Cinquegrani himself testified, the very fact that an opinion letter was prepared indicates that the client

anticipated substantial tax benefits from the transaction. A III: 146/3880–81. Thus, to fault

Shapiro because the opinion letter failed affirmatively to state that the “real reason” for the PICO

transaction was “to provide tax losses” borders on the spurious. At a minimum, Shapiro’s conduct

with respect to the crafting of the PICO opinion letter appears equally consistent with good faith in

his role as a “technician” tasked with making sure the transactions were structured in compliance

with tax law. A III: 140/3857–58 (Cinquegrani testimony); see also A II: 544–45/2865–67 (Six

testimony); A III: 398/4882 (Rydberg testimony).23

                                        ii. Tax Evasion Objective

        Shapiro also challenges the sufficiency of the evidence with respect to the tax evasion

objective of the § 371 conspiracy charged in Count One. “It is elementary that conspiracy is a crime,

separate and distinct from the substantive offense.” United States v. Pinckney, 85 F.3d 4, 8 (2d Cir.

1996). “Although the government need not prove commission of the substantive offense” to secure

a conspiracy conviction, “it must prove that the intended future conduct [the conspirators] agreed

upon includes all the elements of the substantive crime.” Id. (internal quotation marks and


23 For the sake of convenience and to avoid undue repetition, we set forth the evidence with respect to Shapiro’s
involvement in the Add-On tax shelter under the rubric of the tax evasion objective below. Our analysis of that
evidence is, of course, equally applicable in connection with the Klein conspiracy objective.
                                                       24
alterations omitted). In this case, the substantive crime of tax evasion requires proof of “(1) the

existence of a substantial tax debt, (2) willfulness of the nonpayment, and (3) an affirmative act by

the defendant, performed with intent to evade or defeat the calculation or payment of the tax.”

United States v. Litwok, 678 F.3d 208, 215 (2d Cir. 2012) (quotation marks omitted); see 26 U.S.C.

§ 7201.

          The Government’s sole tax deficiency theory at trial was that the Add-On tax shelter offered

investors no reasonable possibility of profit, and that the tax losses resulting from Add-On therefore

could not properly be deducted from the investors’ tax returns. The Government argued that, in

order to create a non-tax explanation for the mechanics of the Add-On transaction, the trial

defendants adopted a false “cover story” proposed by Bolton. That cover story attributed a key step

in the Add-On transaction—the transfer of digital options from the individual partnership to a

newly formed LLC—to a request from trader Andrew Krieger to consolidate accounts for

administrative convenience. There was no meaningful dispute at trial that the “consolidation cover

story” was false.

          The Government argues that sufficient evidence supported the tax evasion objective because

Shapiro “w[as] involved at critical junctures of Add-On’s development, marketing, and defense.” In

what follows, we consider the evidence with respect to Shapiro’s involvement at each of these

“critical junctures.”

          Add-On Development. The parties do not dispute that the strategy for the Add-On tax shelter

was initially proposed by Vaughn and thereafter developed by Vaughn, Coplan, and members of the

investment firm operated by Bolton. Although Shapiro received copies of early e-mails describing a

“precursor concept” to the Add-On shelter, and participated in telephone conferences about that

preliminary idea, the “specifics” of the transaction were only developed subsequently. A III:

                                                   25
237/4241; see A II: 496/2674 (this was “not the way the Add-On transaction ultimately came to

be”). Moreover, Shapiro did not attend an early meeting at which the alleged “cover story” was

discussed, was not involved in drafting the factual section of the Add-On legal opinion letter, and

was excluded from e-mails in which others discussed the economics of the transaction.

         Add-On Marketing. The Government’s claim that Shapiro was involved in marketing the

Add-On shelter rests primarily on his receipt of various e-mails. In June 2000, Coplan sent Vaughn,

Shapiro, and Nissenbaum a proposed e-mail to other E&Y professionals announcing the new Add-

On shelter, and asked them to review for “accuracy and tone.” A IV: 127. That e-mail repeated the

consolidation cover story. Similarly, in July 2000, Coplan sent an e-mail asking Vaughn, Shapiro,

Nissenbaum, and others to “make any final changes” to a draft client solicitation letter. But contrary

to the Government’s assertions, there is no evidence that Shapiro actually or habitually “reviewed”

the Add-On solicitation letters before they were sent to clients. Indeed, according to the trial

testimony of cooperator Belle Six, Shapiro was not among the people who were “part of th[e]

process” of “sending out letters to clients.” A II: 424–25/2391–93.

         Shapiro maintains that he had no reason to understand or suspect the economics of the

Add-On shelter until February 12, 2003—years after the Add-On marketing campaign—when he

received draft “Talking Points” that contained the details necessary to assess the profit potential of

the transaction.24 After reviewing the draft, Shapiro asked whether “the 2:1 ratio”25 describing


24Under the so-called “objective” prong of the economic substance doctrine, transactions that lack profit potential may
be disallowed by the IRS. See Jerome B. Libin, Congress Should Address Tax Avoidance Head-On: The Internal Revenue Code
Needs a GAAR, 30 Va. Tax Rev. 339, 345–46 (2010) (“Some lower courts have viewed ‘economic substance’ as a test
having two separate requirements (subjective business purpose and objective pre-tax profit potential) that must be
satisfied before a transaction will be accorded the tax benefits claimed.”); see also Modern Tax Controversies, 957 Practicing
Law Inst. 478-1, 478-35 (2012) (“To analyze a transaction for the presence of objective economic substance, courts look
to see if there is an objective potential for profit and/or the presence of genuine risk.”).

25 The “2:1 ratio” (profit: premium) refers to the fact that, absent the highly unlikely “home run” scenario discussed post,

the potential payoff of the Add-On transaction before fees was “two times the net investment amount.”
                                                             26
potential payoff was “correct” and what “the impact of fees” was on the profitability of the

transaction. He then learned from Coplan that “[a]pparently, in the [A]dd-[O]n the 2:1 payoff would

not exceed the transaction fees paid to E&Y and Bolton totaling 1.5% of the loss amount since the net

premium was under 1%.” A V: 20 (emphasis added). The Government offers no explanation for

why Shapiro would ask about the payoff ratio and impact of fees if he already knew that the Add-

On shelter lacked profit potential.

         Add-On Defense. The Government further argues that, by “reviewing and approving” a chart

for use in an IRS deposition, Shapiro himself committed an affirmative act of tax evasion. The chart

at issue depicted the “home run” or “sweet spot” scenario in which the Add-On shelter would

produce a huge windfall to the client. Although the Government conceded at trial that “the

numbers on the chart are true,” it argues that the chart was used to mislead the IRS by attempting to

establish a false non-tax motivation for a transaction. In response, Shapiro argues that there is no

evidence that he did anything affirmative with the chart, which correctly sets forth a variety of

outcomes for the transaction, including the extraordinarily unlikely “home run.” At most, Shapiro’s

time records reflect that “he reviewed it” for an hour and a half.

         Finally, the Government points to correspondence regarding the Add-On “amnesty

template” as evidence of Shapiro’s participation in a tax evasion conspiracy.26 It appears that

Shapiro did provide comments on the Add-On amnesty template, although the record does not

reflect the scope or content of his suggestions. The Government faults Shapiro for leaving the

cover story undisturbed in the amnesty template, but it is not at all apparent that Shapiro in fact

knew that the cover story was “bogus.” The Government argues that because Shapiro had seen an


26In December 2001, the IRS announced an amnesty program under which taxpayers who had engaged in tax shelters
could voluntarily disclose those transactions to the IRS in order to avoid potential penalties. The defendants helped to
craft amnesty templates that E&Y’s clients could submit to the IRS.
                                                          27
“instant message” from Vaughn proposing the Add-On concept, he knew that the “consolidation”

business purpose was false. But nothing in the instant message exchange suggested that the Add-On

business purpose was false; instead, the cover story was developed during conference calls and e-

mail correspondence in which Shapiro did not participate.

                                    iii. False Statement Objective

        The third and final objective of the § 371 conspiracy imputed to Shapiro and charged in Count

One, the false statements objective, was clearly directed to the conduct charged in Counts Six and

Seven. See A VI: 420/6161 (“Section 1001 is not only charged as an object of the conspiracy, but is

also charged in Counts Six and Seven as separate substantive offenses against defendants Coplan and

Vaughn . . . .”). As previously noted, Counts Six and Seven charged defendants Coplan and Vaughn

with making false statements to the IRS. The Government does not contend that Shapiro even knew

about the Coplan and Vaughn depositions before they occurred, much less discussed their testimony

with them. There was no separate substantive false statements charge against Shapiro in connection

with his own IRS deposition.

                                  iv. The Conspiracy “As a Whole”

        Having reviewed the record and the arguments of counsel, we conclude that the evidence

against Shapiro is insufficient to support his conviction on Count One. In reaching this conclusion, we

are mindful that the absence of direct evidence is not dispositive, since “the government is entitled to

prove its case solely through circumstantial evidence.” United States v. Rodriguez, 392 F.3d 539, 544 (2d

Cir. 2004). Nevertheless, “[i]f the evidence viewed in the light most favorable to the prosecution gives

equal or nearly equal circumstantial support to a theory of guilt and a theory of innocence, then a

reasonable jury must necessarily entertain a reasonable doubt.” United States v. Huezo, 546 F.3d 174, 193

(2d Cir. 2008) (internal quotation marks omitted). In this case, an essential element of the conspiracy

                                                  28
charged in Count One required proof beyond a reasonable doubt that Shapiro joined the alleged

conspiracy with the “specific intent” to violate the law. United States v. Ogando, 547 F.3d 102, 107–08

(2d Cir. 2008); Rodriguez, 392 F.3d at 545 (“To sustain a conspiracy conviction, the government must

present some evidence from which it can reasonably be inferred that the person charged with

conspiracy knew of the existence of the scheme alleged in the indictment and knowingly joined and

participated in it.”) (emphasis added) (quotation marks omitted). The evidence with respect to Shapiro’s

intent, viewed in the light most favorable to the Government, remains, at best, in equipoise. Because

“[i]t would not satisfy the [Constitution] to have a jury determine that the defendant is probably guilty,”

Sullivan v. Louisiana, 508 U.S. 275, 278 (1993), we conclude that Shapiro’s conviction on Count One

must be reversed.

                             2. Conspiracy Evidence Against Nissenbaum

                                    i. Klein Conspiracy Objective

        PICO Amnesty Template. The principal conspiracy evidence against Nissenbaum relates to his

participation in the development of the PICO amnesty template. See note 26, ante. The Government

asserts that Nissenbaum “drafted, and then circulated to Shapiro and Coplan for their review, a

template for the PICO amnesty submission.” The strongest evidence to support the Government’s

assertion is a February 28, 2002 e-mail Nissenbaum sent to Shapiro and Coplan with the draft PICO

template attached. The text of the e-mail reads as follows: “Gentlemen, your comments. Bob, did you

also want me to do an SDI template [referring to a different tax shelter]?” Because the PICO template

contained false and misleading descriptions of the transaction, the Government claims that

Nissenbaum knowingly participated in providing false information directly to the IRS. But once again,

the record belies the Government’s gloss. Dougherty testified that he “drafted the [PICO] amnesty

letters based on a template from the SISG tool kit,” and that the template “generally tracked the



                                                     29
opinion letter” for the transaction. With respect to Nissenbaum’s role in developing the template,

Dougherty testified as follows:

        My recollection was that Martin Nissenbaum was the reviewer of the template letters
        that I prepared and he provided some non-substantive comments on the final
        version of the letters to go out to the clients.

A II: 235/1641. Dougherty further testified that the “non-substantive comments” Nissenbaum

provided were to “take out the bold” and “correct[] a typo.”

        Advice to Keep CDS Trading Account Open. The e-mail chain regarding the extension of the CDS

trading account, raised with respect to Shapiro above, see Part II.A.1.i, ante, also features in the

conspiracy case against Nissenbaum. In a November 12, 2001 e-mail, Coplan asked Shapiro and

Nissenbaum about a CDS shelter in which “[t]heir swaps have terminated, but Bolton is suggesting that

the partnership be shut down after essentially 13.5 months.” A IV: 219. Coplan’s question was

whether E&Y should “intercede and suggest running another year out with the trading account?”

Nissenbaum responded: “Yes. They sound way too anxious to get out.” From this exchange, the

Government argues that “[t]he defendants were understandably concerned about the taxpayers

appearing ‘too anxious to get out’ of the trading account because that hasty exit would undermine the

false description of the trading account as an investment vehicle.”

        But it appears that, in the context of the e-mail exchange, the pronoun “they” in Nissenbaum’s

two-sentence e-mail is not a reference to anxious “taxpayers.” The e-mail appended to Coplan’s initial

inquiry was a note from Cam Hasseltine, an employee of the Bolton firm, which was managing the

CDS trading accounts. Hasseltine’s e-mail, which suggested the termination of the CDS account, was

addressed to Robert Coplan, Belle Six, and two other E&Y employees—not to the taxpayer clients at

issue. If anyone was “too anxious to get out” of the CDS shelter, it was the Bolton employees managing

the trading accounts, not the taxpayers who entered the transaction.



                                                      30
        Review of Add-On Documents. Finally, the Government points to Nissenbaum’s review of various

Add-On documents as evidence of his participation in the Klein conspiracy. In March 2000, Coplan

sent a draft Add-On amnesty template to Nissenbaum, Shapiro, and another E&Y employee with a

request to look it over “to avoid unnecessary facts or to make it easier to complete accurately.” Twenty

minutes later,27 Nissenbaum replied with a three-line e-mail:

        The disclosure looks fine to me except that I don’t believe that it’s necessary to put
        the specifics of each option trade in the letter. If we do it here, presumably we’d
        have to include the hundreds of trades that are done in PICO.

A IV: 400. Nothing in Nissenbaum’s response evinced a knowing “stamp of approval” for the

consolidation cover story in the Add-On amnesty template. Similarly, Nissenbaum also received a July

2000 e-mail from Coplan suggesting that Nissenbaum and others should make “any final changes” to a

draft Add-On client solicitation letter. But, as with Shapiro, there is no evidence that Nissenbaum

actually “reviewed” the Add-On solicitation letters; nor was he “part of th[e] process” of “sending out

letters to clients.”

                                          ii. Tax Evasion Objective

        With respect to the alleged tax evasion objective of the § 371 conspiracy, Nissenbaum contends

that the evidence is similarly insufficient. Nissenbaum did not participate in telephone conferences or

meetings related to the development of the Add-On shelter. Although Nissenbaum occasionally

received copies of e-mail correspondence related to Add-On, it appears that he responded only once—

in the three-line e-mail quoted above. Indeed, the Government appeared to acknowledge the dearth of

direct evidence as to Nissenbaum in response to his motion for a judgment of acquittal pursuant to

Federal Rule of Criminal Procedure 29. See A III: 516 (Nissenbaum “[a]dmittedly . . . doesn’t have the

same involvement that Mr. Coplan and Mr. Vaughn and Mr. Shapiro do”).



27The time stamp on Coplan’s initial e-mail was 9:16 a.m.; the time stamp on Nissenbaum’s reply was 8:36 a.m. Thus, it
appears that the clock on one of the two computers was off by one hour.
                                                         31
        Instead, the Government’s principal theory of tax evasion liability for Nissenbaum was based

on Pinkerton v. United States, 328 U.S. 640 (1946). Under Pinkerton, “[o]nce a conspiracy has been

established, the criminal liability of its members extends to all acts of wrongdoing occurring during the

course of and in furtherance of the conspiracy.” United States v. Gallerani, 68 F.3d 611, 620 (2d Cir.

1995) (internal quotation marks omitted). Pinkerton is not “a broad principle of vicarious liability that

imposes criminal responsibility upon every co-conspirator for whatever substantive offenses any of

their confederates commit.” United States v. Bruno, 383 F.3d 65, 90 (2d Cir. 2004) (quotation marks

omitted). Instead, Pinkerton provides that “a defendant who does not directly commit a substantive

offense may nevertheless be liable if the commission of the offense by a co-conspirator in furtherance

of the conspiracy was reasonably foreseeable to the defendant as a consequence of their criminal

agreement.” United States v. Parkes, 497 F.3d 220, 232 (2d Cir. 2007) (quotation marks omitted).

         The Government argues that Nissenbaum was guilty under a Pinkerton liability theory because

it was reasonably foreseeable that a coconspirator would commit tax evasion. As previously noted, the

trial defendants (including Nissenbaum) concede that they were aware of Add-On’s lack of profit

potential as of February 2003, when an e-mail exchange revealed the impact of fees on the profitability

of the transaction. See Part II.A.1.ii, ante. The Government argues that, because Nissenbaum was also

aware that the IRS was conducting depositions related to the ongoing audit of the Add-On shelter, it

was reasonably foreseeable to him that a coconspirator would commit tax evasion. The Government

does not, of course, assert the proposition that the mere fact of an ongoing IRS inquiry suggests, much

less shows, criminal intent or knowledge that the subject of the inquiry is unlawful.

         The trouble with the Government’s argument is that “even Pinkerton liability . . . is premised on

a mental state.” United States v. Ferguson, 676 F.3d 260, 279 n.18 (2d Cir. 2011) (citing Pinkerton, 328 U.S.

at 647 (“The criminal intent to do the act is established by the formation of the conspiracy.”)). In other



                                                     32
words, although Pinkerton may permit a broader scope of liability for established coconspirators, the

doctrine does not dilute or erode the basic requirement that “the person charged with conspiracy knew

of the existence of the scheme alleged in the indictment and knowingly joined and participated in it.”

Rodriguez, 392 F.3d at 545 (emphasis added) (quotation marks omitted). The Government’s only

attempt to identify an affirmative act by Nissenbaum that would demonstrate the requisite criminal

intent is the three-line March 2000 e-mail. That is simply not enough.

                                     iii. False Statements Objective

         As previously noted, see Part II.A.1.iii, ante, the false statements objective of the § 371

conspiracy was clearly directed to the conduct charged in Counts Six and Seven. The Government

does not contend that Nissenbaum was aware of or involved in the false statements to the IRS during

the Coplan and Vaughn depositions. There was no separate substantive false statements charge against

Nissenbaum in connection with his own deposition.

                                       iv. The Conspiracy “As a Whole”

        Having examined the evidence against Nissenbaum with respect to each of the three objectives

of the § 371 conspiracy charged in Count One, we turn again to the task of “looking at [the conspiracy]

as a whole.” Cont’l Ore Co., 370 U.S. at 699. Once again, our review of the record and the arguments of

counsel compels the conclusion that the evidence against Nissenbaum is insufficient to support his

conviction on Count One. Viewed in the light most favorable to the Government, the evidence with

respect to Nissenbaum’s intent “gives equal or nearly equal circumstantial support to a theory of guilt

and a theory of innocence.” United States v. Glenn, 312 F.3d 58, 70 (2d Cir. 2002) (internal quotation

marks omitted). Under these circumstances, “a reasonable jury must necessarily entertain a reasonable

doubt.” Id. (quotation marks omitted). Accordingly, we conclude that Nissenbaum’s conviction on

Count One must be reversed.



                                                      33
                    B. Sufficiency of the Evidence Supporting Counts Two and Three

          Defendants Shapiro and Nissenbaum also challenge the sufficiency of the evidence to support

their convictions on Counts Two and Three, which charged all the trial defendants with tax evasion in

violation of 26 U.S.C. § 7201. To prove a violation of § 7201, the Government must establish beyond

a reasonable doubt (1) a substantial tax deficiency; (2) willfulness, meaning the intentional violation of a

known legal duty; and (3) an affirmative act “with the intent to evade or defeat a tax or payment of it.”

United States v. Romano, 938 F.2d 1569, 1571 (2d Cir. 1991). We have already reviewed the evidence

supporting the tax evasion liability of both Shapiro and Nissenbaum in connection with the foregoing

discussion of the tax evasion conspiracy objective. See Part II.B.1.ii, II.B.2.ii, ante. For substantially the

reasons that compel reversal as to Count One,28 we conclude that the convictions of Shapiro and

Nissenbaum on Counts Two and Three must be reversed.29

                              C. Sufficiency of the Evidence Supporting Count Four

          Finally, Nissenbaum challenges the sufficiency of the evidence on Count Four, which charged

him with obstruction of the IRS in violation of 26 U.S.C. § 7212(a). As previously noted, § 7212(a)

prohibits conduct by which a defendant “corruptly or by force or threats of force . . . obstructs or

impedes, or endeavors to obstruct or impede, the due administration of [the internal revenue code].”

26 U.S.C. § 7212(a). “The key words in [§] 7212(a) are ‘corruptly’ and ‘endeavors.’” United States v.


28In her partial dissenting opinion, Judge Kearse suggests that Shapiro and Nissenbaum could be convicted on Counts 2
and 3 under Pinkerton. We disagree because, as noted above, there is insufficient evidence that Shapiro or Nissenbaum
“knew of the existence of the scheme alleged in the indictment and knowingly joined and participated in it.” Rodriguez, 392
F.3d at 545 (quotation marks omitted).

29In her partial dissent, Judge Kearse reaches the opposite conclusion with regard to Shapiro’s and Nissenbaum’s
convictions on Counts 1-3. In response, we simply note that sufficiency challenges are highly fact-specific inquiries that
require a careful examination of the record. See, e.g., Ospina v. Trans World Airlines, Inc., 975 F.2d 35, 37 (2d Cir. 1992)
(“[T]his case turns on whether plaintiffs introduced sufficient evidence to support the jury’s verdict . . . a necessarily fact-
specific inquiry.”). For the reasons stated above, our close review of the record leads us to the conclusion that “the
evidence presented at trial fell considerably more than ‘a trifle short’; but even a trifle short is insufficient.” United States v.
Muniz, 60 F.3d 65, 73 (2d Cir. 1995) (Kearse, J., dissenting).
                                                                 34
Kelly, 147 F.3d 172, 176 (2d Cir. 1998). The District Court instructed the jury as follows:

        To act corruptly means to act with the intent to secure an unlawful advantage or
        benefit either for oneself or for another. Acting corruptly requires consciousness of
        wrongdoing.

A VI: 428/6193–94. Although we have previously declined to read a willfulness requirement into

§ 7212(a), we have held that a substantially similar jury instruction was “as comprehensive and accurate

as if the word ‘willfully’ was incorporated in the statute.” Kelly, 147 F.3d at 177.

        Here, the Government argues that Nissenbaum violated § 7212(a) by causing false and

misleading statements to be submitted to the IRS in response to an IRS Information Document

Request (“IDR”) regarding the Tradehill tax shelter. The evidence with respect to Count Four

principally turns on the implications of the testimony of two E&Y partners who participated in the

Tradehill transaction, Jacob Blank and Martin Flashner, and who testified at trial pursuant to immunity

orders. Count Four originally alleged that the IDR contained four false statements:

        (1) Profit motivation. The first allegedly false statement in the IDR response was that the E&Y

partners had entered into the Tradehill transaction in order to generate profits. After Nissenbaum’s

counsel made a Rule 29 motion on Count Four, the Government agreed to withdraw the allegation that

this statement was “false and misleading” and to redact the Indictment accordingly.

        (2) Euro exposure. The second allegedly false statement in the IDR response, as summarized in

the Redacted Indictment, was that “the Tradehill transaction was intended fully to hedge the partners’

exposure to fluctuation in the euro.” The Redacted Indictment alleged that this statement was false

because “in reality, the transaction had no capacity to do so.” A I: 106.

        The statement at issue appeared in response to the first question in the IDR questionnaire:

“Describe all of your reasons and/or objectives for entering into the Transaction. For each reason

and/or objective, were these reasons and/or objectives achieved?” The IDR response letter, which



                                                     35
was submitted and signed by Proskauer Rose LLP (“Proskauer”) attorney Abraham Gutwein

(“Gutwein”), included a ten-paragraph answer to question one. Among those ten paragraphs, the

Government primarily quarrels with the following passage:

               Partly in order to hedge his exposure to the euro and to offset the losses
               sustained to date with respect to his Cap Gemini holdings, the taxpayer
               entered into the option transactions on November 1, 2000.

               Under the currency option positions purchased and sold, the taxpayer would
               stand the potential of a substantial profit if the euro continued to decline in
               value relative to the dollar (as had been the prevailing trend) at the option
               exercise dates. . . . In that manner the taxpayer intended to fully hedge his
               exposure to fluctuation in the value of the euro.

SA 812.

        The Government argues that the direct examination of Blank and Flashner, the principal

witnesses with respect to Count Four, conclusively established that they did not enter the Tradehill

transaction in order to hedge against exposure to the euro. We disagree. Blank’s testimony, for

example―both on cross-examination and redirect examination―showed that his tax-minimization

purpose was not the only objective of the Tradehill transaction. On direct examination, Blank testified

as follows:

        Q: Did you enter into the transaction in order to hedge your exposure to the euro?

        A: No, I did not.

        ....

        Q: Why then was it not your purpose to hedge the euro?

        A: The purpose of entering into the transaction was really to generate the loss. That
        was the real reason . . . I made my investment. The fact that foreign currency
        options were used, there was an exposure, . . . it certainly was a factor or a competing
        factor that we were able to focus on, but . . . foreign currency exposure was not the
        reason we entered into the deal. The reason was to get the tax loss.

        ....



                                                    36
        Q: What, if any, understanding did you have at the time of the transaction about how
        much of a hedge this transaction could provide?

        A: I had none.

        Q: What, if any, discussions did you have with other members of the transaction
        about how much of a hedge this transaction could provide?

        A: None.

        ....

        Q: This [IDR response] says: In that manner the taxpayer intended to fully hedge his
        exposure to fluctuation in the value of the euro, is that statement true?

        A: It’s not correct.

A II: 588/3037–38. But on cross examination, Blank equivocated by acknowledging that hedging

against fluctuations in the euro was “an objective,” as follows:

        Q. I’m not asking you your primary objective, sir. I’m asking you [whether] an
        objective of entering into th[e] [Tradehill] transaction was to hedge the currency? An
        objective.

        THE COURT. Yes or no. Can you answer it?

        Q. At that time.

        A. At that time, yes.

        ....

        Q. The [IDR] question did not ask you what your primary objective was, did it?

        A. That is correct.

        ....

        Q. So the three objectives that the participants had were to hedge against the
        currency, were to make money, and the obvious, tax motive. That’s why everybody
        is doing this, is that correct, sir?

        ....

        A. Yes.

                                                    37
A II: 609/3121–23. And on redirect examination, the Government harked back to Blank’s testimony

that because the Cap Gemini stock he had received “was not denominated in dollars” but rather “was

denominated in a foreign currency, . . . the justification for entering into the transaction from a business

perspective was to be able to, in effect, hedge and try to reduce the risk associated with owning non-

U.S. dollar denominated investments.” A II: 570/2966–67. It sought clarification:

        Q. On direct examination you said that hedging the euro was a justification for the
        transaction. Do you remember using that word?

        A. Yes, sir, I do.

        Q. What did you mean by that?

        A. At the time we entered into the transaction, I was desirous of assuring that there
        was a business purpose for the transaction, and at that time I did have the foreign
        currency exposure, because, again, the stock that we were awarded in the sale was
        not denominated in dollars, it was in foreign currency, and to the extent that the
        transaction we entered offered, to the best of my knowledge at the time, the
        possibility of trying to mitigate or hedge some of the risk associated with the dollar
        going up or the dollar going down, that to me at that time, based on what I
        understood then, represented a business purpose for entering into this transaction.

        Q. Was it the reason you entered into the transaction?

        A. It was not the primary reason.

A II: 618/3156.

        The record reflects a similar tension with respect to Flashner, who testified on direct

examination that he did not enter the Tradehill transaction in order to hedge his exposure to the euro,

A III: 24/3395, but admitted on cross examination that the E&Y partners discussed the “exchange rate

risk” presented by their receipt of stock denominated in euros, A III: 32/3424. Flashner further

testified that “it would make sense” to protect his investment “by trying to make some money from

this downward movement of the euro against the dollar.” A III: 33/3430–31. Finally, Flashner




                                                    38
admitted that his goals in investing in Tradehill were “two-fold”: to obtain tax losses and “to earn a

profit from the transaction.” A III: 24/3394.

        Faced with obvious internal tension within the testimony of its two principal witnesses on

Count Four, the Government avers that “the jury was entitled to rely on the direct examination.”

Gov’t’s Br. 185–86. But even if the jury fully credited the direct examination, as we must assume here,

that testimony lends implicit support to Nissenbaum’s defense as well. As noted above, Blank’s direct

testimony was that “[t]he purpose of entering into the transaction was really to generate the loss. That

was the real reason . . . I made my investment. The fact that foreign currency options were used, there

was exposure . . . it certainly was a factor or a competing factor that we were able to focus on, but . . .

foreign currency exposure was not the reason we entered into the deal.” A II: 588/3037. The

straightforward implication of Blank’s testimony is that hedging against fluctuations in the euro was not

the primary reason for entering the Tradehill transaction. But that was not the question posed by the

IDR. Question number one prompted the taxpayer to “[d]escribe all of your reasons and/or objectives

for entering the Transaction.” Blank’s statement—in the same sentence excerpted by the

Government—that foreign currency exposure “certainly was a factor” appears consistent with the

statement in the IDR response that the transaction was entered “[p]artly in order to hedge.” SA 812

(emphasis added).

        (3) Non-written understandings. The third allegedly false statement in the IDR response was that

“[t]here were no non-written understandings” among the participants in the Tradehill transaction. .

The Redacted Indictment alleged that this statement was false because “in reality, there was an

understanding among all the parties to the transaction that the E&Y partners would exit their option

positions before the end of 2000, in order to claim tax losses they could use to offset their . . .

income.” A I: 106.



                                                      39
       There was no affirmative testimony about the existence of “non-written understandings”

among the Tradehill participants. In fact, both Blank and Flashner denied engaging in discussions with

any other E&Y partner about exiting their option positions. A II: 578/ 2997, 579/3000, 580/3005

(Blank); A III: 23/3389 (Flashner). Nevertheless, the Government insists that the “entire thrust” of

their testimony was that the partners were entering the Tradehill transaction to generate a tax loss for

the same tax year, and would take the steps necessary to that end.

       Even assuming arguendo that the Government is correct about the “thrust” of the testimony, a

more fundamental defect in this allegation remains: the Tradehill participants retained Gutwein—not

Nissenbaum—to represent them with regard to the IRS audit. Gutwein, who had powers of attorney

from the Tradehill participants, substantially revised a response that Nissenbaum proposed about

“understandings” among the E&Y partners. In a draft IDR response, Nissenbaum noted that “[a]ny

‘understandings’ involved the purchase and contribution of the options, the creation of the various

entities and the sale of the assets that generated the losses.” A V: 130. Gutwein then revised the

response to state that “[t]here were no non-written understandings between the [Tradehill

participants].” Thus, it appears that the language suggested by Nissenbaum was more accurate than the

language of the final IDR response.

       (4) Future referral of business. The final allegedly false statement in the IDR response was that

there was no expectation or referral of any future business to Proskauer, “when in reality, in 2001, the

defendants referred PICO clients to [Proskauer] for opinion letters.” The Government relies on the

fact that about the time Proskauer was completing the legal opinions for the Tradehill shelter, it was

given the paid work of writing PICO opinions, which had to that point been prepared by Arnold &

Porter. Based on the timing, the Government argues that the jury was free to conclude that there was

indeed an “expectation or referral” of future business, rendering the IDR statement to the contrary



                                                    40
false and misleading. But Blank and Flashner did not testify to any expectation or referral of future

business to Proskauer. In the absence of any affirmative proof, we are left only with the “speculation

and surmise” that such an expectation existed. Langston v. Smith, 630 F.3d 310, 314 (2d Cir. 2011) (“[A]

conviction based on speculation and surmise alone cannot stand . . . .”) (quotation marks omitted).

        Having reviewed the record and the arguments of counsel, we conclude that the record

compels reversal of Nissenbaum’s conviction on Count Four. Given the equivocal testimony by Blank

and Flashner and the role of Gutwein in drafting the IDR response, “a reasonable jury must necessarily

entertain a reasonable doubt” as to whether Nissenbaum corruptly obstructed or impeded the IRS.

Glenn, 312 F.3d at 70 (quotation marks omitted).30

                                 III. Propriety of Venue for Count Six,
                           Charging Vaughn with False Statements to the IRS

        Defendant Vaughn challenges the propriety of venue for Count Six, charging him with making

false statements to the IRS during a June 12, 2002 deposition in Nashville, Tennessee, in violation of 18

U.S.C. § 1001.

                                               A. Legal Standard

        Because “[p]roper venue in criminal proceedings was a matter of concern to the Nation’s

founders,” the United States Constitution “twice safeguards the defendant’s venue right.” United States

v. Cabrales, 524 U.S. 1, 6 (1998). Article III requires that “the Trial of all Crimes . . . shall be held in the

State where the said Crimes shall have been committed.” U.S. Const. art. III, § 2, cl. 3. The Sixth

Amendment further provides that “[i]n all criminal prosecutions, the accused shall enjoy the right to a

speedy and public trial, by an impartial jury of the State and district wherein the crime shall have been




30It bears underscoring the fact that Judge Kearse agrees with our reversal of Nissenbaum’s conviction on Count Four on
sufficiency grounds.

                                                          41
committed.” Id. amend VI;31 see also Fed. R. Crim. P. 18 (requiring that “the government must

prosecute an offense in a district where the offense was committed”).

            When the relevant federal statute does not specify how to determine the location where the

crime was “committed,” “[t]he locus delicti must be determined from the nature of the crime alleged and

the location of the act or acts constituting it.” Cabrales, 524 U.S. at 6–7. In conducting this inquiry, we

“must initially identify the conduct constituting the offense . . . and then discern the location of the

commission of the criminal acts.” United States v. Rodriguez-Moreno, 526 U.S. 275, 279 (1999). “Venue is

proper only where the acts constituting the offense—the crime’s ‘essential conduct elements’—took

place.” United States v. Tzolov, 642 F.3d 314, 318 (2d Cir. 2011) (quoting Rodriguez-Moreno, 526 U.S. at

280).

            “When a crime consists of a single, non-continuing act, the proper venue is clear: The crime is

‘committed’ in the district where the act is performed.” United States v. Ramirez, 420 F.3d 134, 139 (2d

Cir. 2005) (other internal quotation marks omitted). In other cases, “where the acts constituting the

crime and the nature of the crime charged implicate more than one location, the Constitution does not

command a single exclusive venue.” United States v. Magassouba, 619 F.3d 202, 205 (2d Cir. 2010)

(internal quotation marks and alterations omitted). Congress has codified the so-called “continuing

offense” rule in 18 U.S.C. § 3237(a), which provides in relevant part:

            Except as otherwise expressly provided by enactment of Congress, any offense
            against the United States begun in one district and completed in another, or
            committed in more than one district, may be . . . prosecuted in any district in which
            such offense was begun, continued, or completed.

            The Government bears the burden of proving that venue is proper. Tzolov, 642 F.3d at 318.

“[T]he venue requirement, despite its constitutional pedigree, is not an element of a crime so as to

require proof beyond a reasonable doubt; rather, venue need be proved only by a preponderance of the


31   “Technically, Article III specifies ‘venue’ and the Sixth Amendment specifies ‘vicinage,’ but that refined distinction is no
                                                                42
evidence.” United States v. Rommy, 506 F.3d 108, 119 (2d Cir. 2007) (emphasis and internal quotation

marks omitted). The propriety of venue is a question of law that we review de novo. United States v.

Drachenberg, 623 F.3d 122, 124 (2d Cir. 2010).

         The federal false statements statute, 18 U.S.C. § 1001(a), makes it a crime, inter alia, “in any

matter within the jurisdiction of the executive, legislative, or judicial branch of the Government of the

United States, knowingly and willfully . . . [to] make[ ] any materially false, fictitious, or fraudulent

statement or representation.” 18 U.S.C. § 1001(a)(2).

         We have considered the issue of venue for a § 1001(a) violation on two prior occasions. In

United States v. Candella, 487 F.2d 1223 (2d Cir. 1973), a case arising in the Southern District of New

York, the defendants were charged with making false statements based on fraudulent affidavits that

were submitted to a municipal branch office in Brooklyn and then conveyed to the Housing and Urban

Development office in Manhattan. Id. at 1227. We held that, although the crime began in the Eastern

District of New York, “it does not follow that the crime then terminated, and that what transpired in

Manhattan was irrelevant for venue purposes.” Id. at 1228. In United States v. Ramirez, 420 F.3d 134 (2d

Cir. 2005), we elaborated upon the reasoning of Candella, holding that, where a false statement was

made in one jurisdiction and then transmitted to another, venue was proper in both jurisdictions. Id. at

143 (holding that venue was proper in the Southern District of New York because the “‘statements

continued to be false and continued to be in the jurisdiction of the United States’ when they finally

reached Manhattan” (quoting Candella, 487 F.2d at 1228)).32




longer of practical importance.” United States v. Royer, 549 F.3d 886, 893 n.8 (2d Cir. 2008).
32 Vaughn seeks to distinguish Candella and Ramirez because both cases involved written false statements in violation of §

1001(a)(3), rather than oral false statements in violation of § 1001(a)(2). To that end, Vaughn contrasts the text of §
1001(a)(3), which prohibits the “mak[ing] or us[ing]” of a written false statement, with the text of § 1001(a)(2), which
prohibits only the “mak[ing]” of an oral false statement. But Candella and Ramirez did not rely upon the subsequent “use”
of the false statements in order to find that venue was properly laid. Moreover, we find no indication in the text of §
1001(a) that subsection (a)(2) is to be treated differently than subsection (a)(3) for purposes of venue.
                                                           43
                                               B. Venue for Count Six

         Vaughn contends that venue for Count Six was improper because his statements were both

made and received during the IRS deposition in Nashville. For that reason, Vaughn argues, the

subsequent review and analysis of his statements by IRS officials in Manhattan afforded no basis for

venue in the Southern District of New York. We disagree.

         We begin by identifying the “essential conduct elements” of § 1001(a)(2). Rodriguez-Moreno, 526

U.S. at 280. In United States v. Ali, 68 F.3d 1468 (2d Cir. 1995), amended on denial of reh’g, 86 F.3d 275 (2d

Cir. 1996), we held for the first time that materiality is a statutory element of all charges under § 1001.

Ali, 68 F.3d at 1474–75; see United States v. Mandanici, 205 F.3d 519, 523 (2d Cir. 2000). Thus, in order

to secure a conviction under § 1001(a)(2), the Government must prove that a defendant (1) knowingly

and willfully, (2) made a materially false, fictitious, or fraudulent statement, (3) in relation to a matter

within the jurisdiction of a department or agency of the United States, (4) with knowledge that it was

false or fictitious or fraudulent.33

         But not all statutory elements constitute “essential conduct elements” within the meaning of

Rodriguez-Moreno. In reviewing the elements of § 1001, the Supreme Court has noted that the statutory

requirement that the false statement be made “in any matter within the jurisdiction . . . of the United

States” is “jurisdictional language [that] appears in a phrase separate from the prohibited conduct” and

is simply a “predicate circumstance” of the offense. United States v. Yermian, 468 U.S. 63, 68–69 (1984)

(quotation marks omitted). Similarly, the mens rea requirement constitutes “a circumstance element that

does not contribute to determining the locus delicti of the crime.” United States v. Oceanpro Indus., Ltd., 674


33 Since Ali, we have occasionally stated the elements of a § 1001 false statements charge without mentioning the materiality
element. See, e.g., United States v. Wiener, 96 F.3d 35, 37 (2d Cir. 1996) (“To convict a defendant of violating Section 1001,
the government must prove that the defendant: (i) knowingly and willfully, (ii) made a statement, (iii) in relation to a matter
within the jurisdiction of a department or agency of the United States, (iv) with knowledge that it was false or fictitious and
fraudulent.”). In light of our explicit holding that “materiality is indeed an element of the offense,” Ali, 68 F.3d at 1475,
our subsequent failure to incorporate materiality into our standard recitation of the statutory elements of § 1001 appears to
be the result of a simple oversight.
                                                              44
F.3d 323, 329 (4th Cir. 2012).34 Thus, the essential conduct prohibited by § 1001(a)(2) is the making of

a materially false, fictitious, or fraudulent statement.

          In this case, the materiality requirement proves dispositive with respect to venue. “Under

§ 1001, a statement is material if it has a natural tendency to influence, or be capable of influencing, the

decision of the decisionmaking body to which it was addressed, or if it is capable of distracting

government investigators’ attention away from a critical matter.” United States v. Adekanbi, 675 F.3d

178, 182 (2d Cir. 2012) (internal citations, quotation marks, and alterations omitted). Accordingly,

whether Vaughn’s false statements were material turns on the tendency or capacity of those statements

to influence the decisionmaking body at issue—in this case, the IRS.

          Proving the materiality of Vaughn’s false statements in Tennessee necessarily requires evidence

that those statements were conveyed to or had an effect on the IRS investigators working in the

Southern District of New York. Oceanpro, 674 F.3d at 329; see United States v. Salinas, 373 F.3d 161, 167

(1st Cir. 2004) (“When materiality is a critical component of the statutory definition, it makes perfect

sense to consider the crime as continuing into the district in which the effects of the false statement are

felt.”); United States v. Ringer, 300 F.3d 788, 792 (7th Cir. 2002) (finding venue in the district where the

investigation was “reasonably likely to be affected by [the defendant’s] statements”); but see United States

v. Smith, 641 F.3d 1200, 1208 (10th Cir. 2011) (finding venue, where false statement was not recorded,

only in the jurisdiction where the false statement was made). We therefore conclude that venue for




34 Cf. United States v. Clenney, 434 F.3d 780, 782 (5th Cir. 2005) (holding that the intent element of the parental kidnapping
statute, 18 U.S.C. § 1204, “merely speaks to the offender’s mens rea as he commits the conduct essential to the crime; it is
plainly not an ‘essential conduct element’ as required by Rodriguez-Moreno”); Ramirez, 420 F.3d at 144 (“While a scheme to
defraud is certainly one of three essential elements of mail fraud, it is not an essential conduct element. . . . It is the mens rea
element of mail fraud.”); United States v. Bowens, 224 F.3d 302, 313 (4th Cir. 2000) (holding that language “defin[ing] the
requisite intent for the offense” of harboring a fugitive, 18 U.S.C. § 1071, was not an essential conduct element).

                                                                  45
Count Six was proper in the Southern District of New York.35

         This result is fully consistent with our holdings in Candella and Ramirez. It is undisputed that

Vaughn “ma[de]” the false statements at issue during the IRS deposition in Nashville—but “it does not

follow that the crime then terminated, and that what transpired in Manhattan was irrelevant for venue

purposes.” Candella, 487 F.2d at 1228. In Ramirez, the offense began in New Jersey, where the

fraudulent paperwork was filed, and ended in the Southern District of New York, the jurisdiction to

which New Jersey officials forwarded the paperwork. Ramirez, 420 F.3d at 137–38. Similarly, the

instant offense case began in Tennessee, where Vaughn made the false statements to IRS officials, but

continued into the Southern District of New York, where his deposition transcript was reviewed and

discussed by IRS officials in connection with the ongoing E&Y audit. The fact that Vaughn’s

statements “‘continued to be false and continued to be in the jurisdiction of the United States when

they finally reached Manhattan,’” Ramirez, 420 F.3d at 143 (quoting Candella, 487 F.2d at 1228)),

confirms our view that venue was proper in the Southern District of New York.

         On occasion, we have supplemented our venue inquiry with a “substantial contacts” test that

“takes into account a number of factors—the site of the defendant’s acts, the elements and nature of

the crime, the locus of the effect of the criminal conduct, and the suitability of each district for accurate

factfinding.” United States v. Reed, 773 F.2d 477, 481 (2d Cir. 1985). Since Reed, we have alternately

applied and ignored the substantial contacts test. Compare United States v. Royer, 549 F.3d 886, 893 (2d

Cir. 2008) (citing Reed with approval); United States v. Saavedra, 223 F.3d 85, 92–93 (2d Cir. 2000) (same);

with United States v. Tzolov, 642 F.3d 314, 321 (2d Cir. 2011) (“Though Reed refers to a ‘substantial

contacts rule’ for determining venue . . . it is clear that the [court] regarded the locale of the defendant’s




35Vaughn similarly argues that the grand jury lacked jurisdiction to return Count 6 of the Superseding Indictment because
the offense was committed outside the district where the jury was impaneled. This challenge fails for substantially the same
reasons as his venue challenge. See Part III.C, ante.
                                                            46
acts as a sufficient basis for establishing venue.” (alteration in original) (other internal quotation marks

omitted)).

        We have previously held, and we now clarify, that use of the substantial contacts test may be

appropriate where, as here, the defendant “argue[s] that his prosecution in the [contested district] . . .

[will] result[ ] in a hardship to him, prejudice[ ] him, or undermine[ ] the fairness of his trial.” United

States v. Magassouba, 619 F.3d 202, 205 n.2 (2d Cir. 2010). We think the District Court in this case

proceeded with the required care by considering the factors enumerated in Reed and Saavedra before

concluding that “the substantial contacts analysis weighs in favor of venue in this district.” Vaughn

does not appear to challenge the substance of that determination on appeal.

                             IV. Admission of Graham Taylor Testimony

        In addition to their validity, sufficiency, and jurisdictional challenges, the trial defendants also

mount a variety of evidentiary challenges. In the first of these, they argue that the District Court erred

in admitting the testimony of Graham Taylor, a tax attorney who worked at the law firm of Pillsbury

Madison and who indisputably committed a variety of crimes involving tax shelters unrelated to this

case. We review the District Court’s rulings regarding the admissibility of evidence at trial for abuse of

discretion. United States v. Williams, 585 F.3d 703, 707 (2d Cir. 2009); cf. In re Sims, 534 F.3d 117, 132 (2d

Cir. 2008) (explaining that the term of art “abuse of discretion” includes errors of law).

        In 1999, Taylor had a series of discussions about the CDS transaction with E&Y partner David

Smith, the defendant in this action who was a fugitive at the time of trial. Taylor drafted an initial

opinion letter regarding the CDS transaction, and Smith eventually brought the transaction and the

draft opinion letter to E&Y. Taylor’s draft opinion letter contained a variety of statements regarding

the CDS transaction that he knew were false, including statements that (1) the purpose of the

partnership was investment profit; (2) the investors would have money at risk; and (3) that early



                                                      47
termination of the swap was not predetermined. Taylor testified that he and Smith had agreed that

these core elements of the transaction could not be disclosed in the opinion letter if the transaction

were to yield the intended tax benefits. Other than a brief phone call with two unknown E&Y

employees in June 1999, Taylor had no contact with anyone else at E&Y. E&Y ultimately engaged

Brent Clifton at Locke Liddell rather than Taylor to write the CDS opinion letter.

        The defendants moved to exclude Taylor’s testimony prior to trial, arguing that his testimony

would consist primarily of recounting his conversations with Smith. The defendants argued that, since

there was no evidence that the substance of those conversations had been relayed to the defendants,

Taylor’s testimony was not relevant. The Government conceded that it would not produce direct

“evidence that Taylor communicated directly with anyone at E&Y regarding what was falsely stated in,

or intentionally omitted from, his draft opinion,” but argued that a jury could infer that “those matters

necessarily would have been conveyed by Smith to one or more of the defendants.” The District Court

denied the defendants’ motion and allowed the Government to present Taylor’s testimony, while

warning that the Government would be required to “connect up” the evidence.

        On appeal, the defendants principally argue that by admitting Taylor’s testimony, the District

Court misunderstood its obligations under Federal Rule of Evidence 104(b), which governs questions

of conditional relevance. Rule 104(b) provides that “[w]hen the relevance of evidence depends on

whether a fact exists, proof must be introduced sufficient to support a finding that the fact does exist.

The court may admit the proposed evidence on the condition that the proof be introduced later.” Fed

R. Evid. 104(b). When faced with a question of conditional relevance, the district court should

“examine[ ] all the evidence in the case and decide[ ] whether the jury could reasonably find the

conditional fact . . . by a preponderance of the evidence.” Huddleston v. United States, 485 U.S. 681, 690

(1988). In this case, the defendants argue that the relevance of Taylor’s testimony depended upon a



                                                    48
preliminary “conditional fact”—that the conversations between Taylor and Smith were ultimately

conveyed to the defendants. In the absence of evidence that Taylor had substantive conversations with

anyone else at E&Y, or that Smith told anyone at E&Y about his conversations with Taylor, the

defendants argue that the Government failed to carry its burden to prove the conditional fact by a

preponderance.

        Despite the Government’s apparent failure to confront the Rule 104(b) analysis on appeal, we

are persuaded that Taylor’s testimony was admissible as direct evidence of the conspiracy. As a

preliminary matter, we note that the draft opinion letter prepared by Taylor and the final opinion letter

issued by Locke Liddell were substantially similar, and that some passages appeared to be copied nearly

verbatim. Indeed, even the defendants acknowledge that “it was certainly reasonable to conclude that

Locke Liddell had received a copy of Taylor’s letter, and that it had used the letter as a starting point

for its own.” Thus, Taylor’s testimony about the content of the draft opinion letter was independently

admissible as to the circumstances manifesting the formation of the conspiracy.

        Taylor’s testimony about his conversations with Smith admittedly presents a closer question of

conditional relevance. Taylor testified at length about the various facts about the CDS transaction that

had to be omitted from the tax opinion or described in misleading terms. As the Government notes,

“what is striking about Taylor’s concerns is that they are precisely the same facts that the defendants, in

e-mail after e-mail, cautioned people against revealing to the IRS.” Based on these similarities, the

District Court concluded that a reasonable jury could infer that Taylor’s concerns were passed on to the

defendants. In the circumstances presented here, we agree. Although the defendants protest that there

is no evidence that Taylor communicated directly with the defendants, we have never required a

statement to be disseminated to each member of the conspiracy in order to be admissible against the

whole. Cf. United States v. Friedman, 854 F.2d 535, 562 (2d Cir. 1988) (“[T]here is no requirement that



                                                     49
each member of a conspiracy conspire directly with every other member of the conspiracy.”).

Accordingly, we affirm the District Court’s decision to admit Taylor’s testimony.

                              V. Admission of Coconspirator Statements

        Defendant Vaughn, in an argument joined by each of the trial defendants, argues that the

District Court committed reversible error by admitting the out-of-court statements of more than 20

alleged coconspirators. Federal Rule of Evidence 801 provides that a statement is not hearsay if it is

both offered against a party and is “made by the party’s coconspirator during and in furtherance of the

conspiracy.” Fed. R. Evid. 801(d)(2)(E). To admit hearsay testimony under Rule 801(d)(2)(E), the

district court “must find (a) that there was a conspiracy, (b) that its members included the declarant and

the party against whom the statement is offered [(the “non-offering party”)], and (c) that the statement

was made during the course of and in furtherance of the conspiracy.” United States v. Alameh, 341 F.3d

167, 176 (2d Cir. 2003) (quotation marks omitted). These are “preliminary questions of fact” to be

resolved by the district court under a preponderance of the evidence standard. Bourjaily v. United States,

483 U.S. 171, 175 (1987).

        We review for clear error a district court’s findings as to whether “there was a conspiracy

involving the declarant and the nonoffering party, and [whether] the statement was made during the

course and in furtherance of the conspiracy.” In re Terrorist Bombings of U.S. Embassies in E. Africa, 552

F.3d 93, 137 (2d Cir. 2008) (quotation marks omitted) (alteration in original). As previously noted, we

review a district court’s determination as to the admissibility of evidence at trial for abuse of discretion.

Williams, 585 F.3d at 707.

        Prior to trial, the Government identified 50 people as coconspirators with the defendants,

including central figures such as David Smith, Peter Cinquegrani, and Belle Six. When the

Government offered out-of-court statements of the alleged coconspirators at trial, the defense objected



                                                     50
that the Government had not carried its burden as to the elements of the coconspirator exception. The

District Court admitted the evidence subject to connection under the procedure established in Bourjaily

v. United States, 483 U.S. 171 (1987), which permits the district court to “examine the hearsay statements

sought to be admitted” in “making a preliminary factual determination.” Id. at 181. At the close of the

Government’s case, the defense filed a motion to strike the out-of-court statements of the alleged

coconspirators. After holding oral argument on the motion and requesting copies of certain exhibits

for additional review, the District Court made a blanket ruling that “the prerequisites of Rule

801(d)(2)(E) have been shown by a preponderance of the evidence with respect to each of the

conditionally admitted statements.”

        The defendants argue on appeal that the District Court’s blanket admission of the

coconspirator statements transgresses the “limit[s] [on] the proper use of Rule 801(d)(2)(E) to admit

coconspirator testimony.” United States v. Gigante, 166 F.3d 75, 82 (2d Cir. 1999). Specifically, Vaughn

argues that, as to most or all of the alleged coconspirators, the Government failed to prove that they

had the intent to join and further an illegal venture. See id. at 83 (“It is the unity of interests stemming

from a specific shared criminal task that justifies Rule 801(d)(2)(E) in the first place . . . .”). For

example, the defendants argue that two outside accountants, Fred Goldman and Robert Cooper, were

“merely outside functionaries” and “cannot be considered ‘co-conspirators’ with the defendants under

any reasonable definition of the term.”

        In response, the Government accuses Vaughn of “cherry-pick[ing]” testimony to argue his case

when there was “ample evidence” to establish that Goldman, Cooper, and others were coconspirators

with the defendants. In particular, the Government notes that Cooper acknowledged at trial that he

had given false and misleading testimony during an IRS tax audit and that he believed he was helping

clients commit tax evasion when he signed tax returns for the Add-On transaction.



                                                      51
        Upon review of the foregoing arguments, it appears that the defendants’ fundamental objection

to the coconspirator evidence relates to the generalized nature of the District Court’s ruling. See

Vaughn Reply 34 (“In point of fact, it is the summary fashion by which the District Court dispensed

with these detailed, specific objections by the Defendants which forms the basis of Vaughn’s argument

concerning this point on appeal.”). Although the blanket ruling by the District Court certainly makes

appellate review more difficult, we have never required the district court to make particularized rulings

or conduct separable analyses with respect to each coconspirator, much less each coconspirator

statement. Cf. United States v. Al-Moayad, 545 F.3d 139, 173 (2d Cir. 2008) (vacating the judgment

because “[t]he court made no findings, by a preponderance of the evidence or otherwise, about the

existence of a conspiracy” (emphasis added)). The record makes clear that the able and experienced

district judge reviewed the defendants’ motion papers, held oral argument, obtained additional evidence

from the Government, applied the correct legal standard, and made a considered oral ruling. In light of

these facts, the District Court did not clearly err in its factual determination that the out-of-court

statements were made in furtherance of the conspiracy, and therefore did not abuse its discretion by

admitting the out-of-court statements under the coconspirator exception.

              VI. Exclusion of Portions of Coplan and Vaughn Deposition Transcripts

        Coplan and Vaughn argue that the District Court abused its discretion by excluding from

evidence portions of their deposition transcripts. As part of an IRS “promoter exam” of E&Y,36 the

IRS deposed both Coplan and Vaughn in June 2002. The deposition transcripts formed the basis for

Counts Six and Seven of the Redacted Indictment, which charged Coplan and Vaughn with making

false statements to the IRS. At trial, the Government sought to introduce only the portions of the

deposition transcripts containing the false statements alleged in Counts Six and Seven. Coplan and



36A “promoter exam” (as opposed to an “income tax exam”) aims to determine (1) whether the entity under examination is
a principal or an organizer under the tax laws, and (2) whether the underlying transactions constitute tax shelters.
                                                         52
Vaughn sought to admit their entire deposition transcripts in order to demonstrate that the statements,

even if false, were not material to the promoter exam. The District Court thereafter accepted certain

counter-designations proposed by the defendants, but refused to admit the entire transcripts, holding

that the excluded portions were “largely inadmissible hearsay offered by defendants, or they [we]re

simply irrelevant to the issues here.”

        Once again, we review a district court’s determination as to the admissibility of evidence at trial

for abuse of discretion. Williams, 585 F.3d at 707.

                                          A. The Alleged Error

        Coplan and Vaughn argue that, in excluding more than 80 percent of the deposition transcripts,

the District Court erred by (1) ruling that the bulk of the deposition transcripts constituted hearsay;

(2) failing to admit the statements under the rule of completeness; and (3) failing to admit the

statements under the state of mind exception to the hearsay rule.

                                               1. Hearsay

        Under Federal Rule of Evidence 801, a hearsay statement is an out-of-court “assertion” that is

“offer[ed] . . . to prove the truth of the matter asserted in the statement.” Fed. R. Evid. 801(a) & (c); see

United States v. Marin, 669 F.2d 73, 84 (2d Cir. 1982) (“When the defendant seeks to introduce his own

prior statement for the truth of the matter asserted, it is hearsay, and it is not admissible.”). Here,

Coplan and Vaughn challenge the District Court’s predicate ruling that the bulk of the deposition

transcripts were offered for the truth of the matter asserted. But as the Government tacitly concedes,

see Gov’t’s Br. 232, the questions posed by the IRS agent were not hearsay, because as a matter of law,

questions are not “assertions” within the meaning of Rule 801. See United States v. Oguns, 921 F.2d 442,

449 (2d Cir. 1990) (“An inquiry is not an ‘assertion,’ and accordingly is not and cannot be a hearsay




                                                      53
statement.” (quotation marks omitted)). Thus, the District Court erred by invoking the hearsay rule to

exclude the questions contained in the deposition transcripts.

       The hearsay status of the defendants’ responses presents a closer question. Coplan insists that

his responses were not offered for the truth of the matter asserted, but to demonstrate “the overall

purpose of the interview, the context in which the charged statements were made, and [his] willingness

to cooperate fully in the interview.” Coplan Reply 31 n.5. The Government counters that Coplan’s

true purpose was to convince the jury that, in the course of a lengthy deposition, he was mostly

truthful. The Government’s contention finds support in a letter brief from Coplan’s counsel, which

made clear that he wished to admit the entire deposition transcript in order to show “his forthcoming

approach to the proceeding.” SA 303. In light of these facts, the District Court did not abuse its

discretion by invoking the hearsay rule to exclude the deposition responses.

                                     2.   “Rule of Completeness”

       Under Federal Rule of Evidence 106, where a party introduces all or part of a recorded

statement, an adverse party may require the introduction of any other part that “in fairness ought to be

considered at the same time.” Fed. R. Evid. 106. The so-called “rule of completeness” provides that

“even though a statement may be hearsay, an omitted portion of the statement must be placed in

evidence if necessary to explain the admitted portion, to place the admitted portion in context, to avoid

misleading the jury, or to ensure fair and impartial understanding of the admitted portion.” United

States v. Kopp, 562 F.3d 141, 144 (2d Cir. 2009) (quotation marks omitted). The rule “does not,

however, require the admission of portions of a statement that are neither explanatory of nor relevant

to the admitted passages.” Id. (quotation marks omitted).

       In this case, Coplan and Vaughn argue that the District Court erred in concluding that portions

of the transcript offered under Rule 106 could still be excluded under the hearsay rule. Although the



                                                   54
Government initially misstated the standard below, Coplan identified the mistake almost immediately,

and there is no indication that the District Court misapprehended or misapplied the Rule 106 standard

in electing to admit the defendants’ counter-designations but not the entire transcripts. Citing the

relevant standard from United States v. Jackson, 180 F.3d 55, 73 (2d Cir. 1999), the District Court stated

that it was “[u]sing [Rule] 106 as a filter or a polestar” in refusing to admit the deposition transcripts in

their entirety, but admitting a number of counter-designations. We find no abuse of discretion in that

determination.

                                     3. “State of Mind” Exception

        Federal Rule of Evidence Rule 803(3) provides a hearsay exception for “[a] statement of the

declarant’s then-existing state of mind . . . or emotional, sensory, or physical condition.” Fed. R. Evid.

803(3). The defendants contend that the excluded portions of the transcript were admissible under this

“state of mind” exception. In particular, Coplan argues that a statement evincing his confusion about

the definition of a “digital option” should have been admitted “to show [his] lack of understanding of

some of the financial instruments involved.” Coplan Br. 83. But although Coplan raised Rule 803(3)

“in general terms” below, it appears that his current argument—that certain statements were admissible

to prove his lack of technical acumen—was never presented to the District Court. A III: 218/4167

(District Court ruling noting that defendants “haven’t given any specificity of statements that show

state of mind of Vaughn or Coplan”).

                                               B. Prejudice

        In any event, even assuming arguendo that the District Court erred by not admitting the entirety

of the deposition transcripts, the error was harmless. Fed. R. Crim. P. 52(a) (defining “harmless error”

as “[a]ny error, defect, irregularity, or variance that does not affect substantial rights”). The defendants

argue that the erroneous exclusion “gutted” their defense that the false statements “were, at best,



                                                     55
ancillary to the investigation.” Coplan Br. 85. But in the full context of the record, it is clear that the

defendants had ample opportunity to make these arguments through their cross-examination of the

IRS agent and their closing arguments. Moreover, the jury heard testimony explaining how all of the

information sought by the IRS was material to the promoter exam that was the subject of the

deposition. On this record, we conclude that, even if the exclusion of the deposition testimony was

erroneous, the error was harmless. See United States v. Farhane, 634 F.3d 127, 164 (2d Cir. 2011)

(deeming harmless the exclusion of state of mind evidence where Government’s contrary evidence was

“clearly overwhelming”); United States v. Song, 436 F.3d 137, 140 (2d Cir. 2006) (deeming harmless the

erroneous exclusion of state of mind evidence where defendant “was permitted to testify in sufficient

detail as to his theory of the case” and Government presented overwhelming evidence of guilt).

                                   VII. Alleged Prosecutorial Misconduct

        Shapiro, joined by Coplan and Vaughn, argues that the Government committed prosecutorial

misconduct by introducing surprise arguments and misrepresenting evidence in its rebuttal summation.

Specifically, the defendants challenge (1) the Government’s “surprise” arguments about client

responses to the PICO IDR; and (2) the Government’s description of COBRA as a “trick” and an

“amazing” and “extraordinary” distortion of the relevant tax regulations.37

        As a general matter, a defendant asserting that a prosecutor’s remarks warrant a new trial “‘faces

a heavy burden, because the misconduct alleged must be so severe and significant as to result in the

denial of his right to a fair trial.’” United States v. Banki, 685 F.3d 99, 120 (2d Cir. 2012) (quoting United

States v. Locascio, 6 F.3d 924, 925 (2d Cir. 1993) (alterations omitted)); see also United States v. Whitten, 610

F.3d 168, 202 (2d Cir. 2010) (“We will reverse on the ground of prosecutorial misconduct only if that


37 Shapiro also argues that the Government’s rebuttal summation mischaracterized the record by telling the jury that

Dougherty had “told” them that “Mr. Shapiro lied about why the S corporation was needed” for the COBRA transaction.
Because we have already concluded that Shapiro’s conspiracy conviction must be reversed on sufficiency grounds, we
decline to address this argument.

                                                         56
misconduct caused substantial prejudice by so infecting the trial with unfairness as to make the

resulting conviction a denial of due process.” (internal quotation marks omitted)). “In considering

whether inappropriate remarks rise to the level of prejudicial error, we examine ‘the severity of the

misconduct, the measures adopted to cure the misconduct, and the certainty of conviction absent the

misconduct.’” United States v. Gansman, 657 F.3d 85, 96 (2d Cir. 2011) (quoting United States v. Caracappa,

614 F.3d 30, 41 (2d Cir. 2010)).

        With respect to the “surprise” rebuttal argument, it is well established that “[r]ebuttal provides

the government with the opportunity to respond to defendant’s arguments. It does not allow the

government to bring in new matters.” United States v. Giovanelli, 945 F.2d 479, 495 (2d Cir. 1991)

(quotation marks omitted). In context, however, it appears that the “surprise” PICO IDR argument

was briefly discussed in the Government’s opening summation as “one of the most galling examples”

of statements prepared by the defendants that falsely described their clients’ subjective intent. The

Government then returned to the PICO IDR argument in rebuttal, highlighting the fact that none of

the defense counsel had addressed the PICO IDR responses. Returning to an argument noted—

although not emphasized—by the Government in its opening summation cannot be regarded as

“deceitful and unfair.” Shapiro Br. 83. In the context of a rebuttal summation that spanned some 120

pages of trial transcript, any misconduct here cannot be deemed severe. See United States v. Newton, 369

F.3d 659, 681 (2d Cir. 2004) (cautioning against “disproportionate emphasis [on] isolated incidents of

alleged error”).

        The defendants also challenge the Government’s description of the COBRA transaction as a

“trick” and an “amazing” and “extraordinary” distortion of the relevant tax regulations. This argument

is equally unpersuasive. It is well established that the Government “has broad latitude in the inferences

it may reasonably suggest to the jury during summation.” United States v. Edwards, 342 F.3d 168, 181 (2d



                                                    57
Cir. 2003) (quotation mark omitted). In this case, the Government had presented ample evidence to

support the inference that COBRA—a shelter that, rather than deferring or converting taxes,

eliminated tax liability altogether—was based on an aggressive, although not necessarily unlawful,

interpretation of the tax code. See, e.g., A II: 364/2149 (testimony of Belle Six) (“We did look at

elimination strategies in [the VIPER Group]. The consensus was not that we wouldn’t sell them, but

that it would be very unlikely that Ernst & Young would ever reach a level of authority to sell them.”).

The Government’s comments about COBRA in rebuttal summation, “while arguably imprecise, were

by no means unreasonable in light of the evidence presented at trial and the nature of the charged . . .

scheme.” United States v. Cohen, 427 F.3d 164, 170 (2d Cir. 2005). For that reason, we find the

defendants’ assertions of prosecutorial misconduct to be without merit.

                                          VIII. Jury Instructions

        Coplan, Shapiro, and Nissenbaum argue that the District Court’s jury instructions were flawed

in three respects: (1) the instructions on Count One, the conspiracy to defraud charge, unfairly

emphasized the Government’s theory of the case and omitted their theory of defense; (2) there was no

factual basis for the conscious avoidance instruction in connection with Counts Two and Three, the tax

evasion charges; and (3) the instructions on Counts Two and Three contained an improper definition

of “economic substance.”

        As a general matter, we review a properly preserved claim of error regarding jury instructions de

novo, reversing only where, “viewing the charge as a whole, there was a prejudicial error.” United States v.

Aina-Marshall, 336 F.3d 167, 170 (2d Cir. 2003). The trial court “enjoys broad discretion in crafting its

instructions[,] which is only circumscribed by the requirement that the charge be fair to both sides.”

United States v. Brand, 467 F.3d 179, 205 (2d Cir. 2006) (quotation marks omitted). A defendant

challenging a district court’s refusal to give a requested jury instruction carries the “heavy burden . . . .



                                                      58
[of showing] that his proposed charge accurately represented the law in every respect, and that the

charge actually given, viewed as a whole, prejudiced him.” United States v. Feliciano, 223 F.3d 102, 116

(2d Cir. 2000) (internal quotation marks omitted).

                                A. Instructions on the Defense Theory

         First, the defendants argue that the jury instructions on Count One omitted their theory of

defense and unfairly emphasized the Government’s theory of guilt. Although a defendant is “entitled

to have the court charge the jury on any defense theory for which a foundation existed in the record, he

[is] not necessarily entitled to have that instruction communicated to the jury in the language of his

choice.” Brand, 467 F.3d at 205 (quotation marks omitted) (alteration in original). “We will vacate a

conviction on account of a missing requested instruction if (1) the requested instruction was legally

correct; (2) it represents a theory of defense with basis in the record that would lead to acquittal; and (3)

the theory is not effectively presented elsewhere in the charge.” United States v. Prawl, 168 F.3d 622, 626

(2d Cir. 1999) (internal quotation marks omitted).

        In this case, the defendants proposed a jury instruction on Count One that emphasized the

distinction between acts that made the IRS’s job more difficult and acts that were done deceitfully or

dishonestly. Their requested instruction included a number of examples that, in the defendants’ view,

could not constitute a conspiracy to defraud, in order to advance the defense theory that their conduct

was legitimate advocacy on behalf of their clients. See, e.g., A VI: 262 (proposed jury instruction) (“It is

not illegal simply to make the IRS’s job harder. This is particularly true for the defendants, whose

professional obligations as attorneys or certified public accountants required them to represent the

interests of their clients vigorously in their dealings with adversaries, such as the IRS.”). The District

Court adopted the substance of the proposed charge, but declined to include the defendants’ examples




                                                     59
or to inform the jury about the special obligations of tax professionals who represent clients in an

adversarial setting.38

            We affirm the District Court’s ruling primarily because the defendants’ proposed charge did not

“accurately represent[ ] the law in every respect.” Feliciano, 223 F.3d at 116 (quotation marks omitted).

The examples of purportedly lawful conduct proffered by the defendants included the following: “an

agreement between witnesses not to tell the government something unless specifically asked about it;


38   With respect to the conspiracy to defraud charge, the District Court instructed the jury as follows:

                     A conspiracy to defraud the United States does not necessarily involve cheating the
            government out of money or property. The statute also includes conspiracies to interfere with or
            obstruct any lawful government function by fraud, deceit, or any dishonest means. I instruct you that
            the IRS is an agency of the United States government. The term “conspiracy to defraud the United
            States” therefore means that the defendants and their alleged co-conspirators are accused of
            conspiring to impede, impair, obstruct or defeat, by fraudulent or dishonest means, the lawful
            functions of the IRS to ascertain taxes and to collect lawfully due and owing tax revenue.

                      Only conduct that both is intended to impede the lawful functions of a government agency
            and is fraudulent or dishonest will support a charge of conspiracy to defraud a government agency. A
            conspiracy to impede the functions of a government agency by fraudulent or dishonest means may
            include such things as altering documents after they have been demanded by the government agency,
            creating false documents, destroying records, making false statements, attempting to induce others to
            make false statements, or engaging in any other fraudulent or deceptive conduct that would have the
            effect of impairing the ability of the government agency to determine material aspects of a
            transaction. By giving you these examples, ladies and gentlemen, I do not mean to suggest that these
            are the only actions that could impede the IRS by fraudulent or dishonest means, nor am I expressing
            any view as to whether conduct similar to these examples actually took place here. That’s for you to
            decide.

                       Not all conduct that impedes the lawful functions of a government agency is illegal. To be
            unlawful, that conduct has to entail fraud, deceit, or other dishonest means. It is not illegal simply to
            make the IRS’s job harder. Only an agreement to engage in conduct that tends to impede the IRS, and also involves
            fraudulent, deceitful or dishonest means, constitutes an illegal agreement to defraud the United States.

                      It is not necessary that the government or the IRS actually suffer a financial loss from a
            scheme. A conspiracy to defraud exists when there is an agreement to impede, impair, obstruct, or
            defeat, in any fraudulent or dishonest manner, the lawful functions of the IRS. One cannot use
            deception or dishonest means to impede, impair, defeat, or obstruct the IRS, even to protect a
            legitimate tax position.

                     Where, however, there is an agreement to impede, impair, obstruct, or defeat the lawful
            functions of the IRS by fraudulent, deceptive, or dishonest means, the first element is satisfied
            regardless of whether the means of doing so in that particular instance are or are not unlawful in and
            of themselves.

                      That’s the first object that’s alleged here, defrauding the IRS and the United States.

A VI: 419/6157–59 (emphasis added).
                                                                    60
advice from an attorney to a client to assert his constitutional right not to speak to government

investigators; an agreement not to create a document that individuals had no obligation to create.”

A VI: 262. Although these acts are not necessarily deceitful, no bright line rule excludes such acts from

supporting a conspiracy to defraud. See Cont’l Ore Co. v. Union Carbide & Carbon Corp., 370 U.S. 690, 707

(1962) (“[I]t is well settled that acts which are in themselves legal lose that character when they become

constituent elements of an unlawful scheme.”). We are not unsympathetic to the defendants’ view that

a lay jury may struggle to fully apprehend the obligations of tax professionals zealously (and lawfully)

representing clients before the IRS. Nevertheless, because the current understanding of the Klein

doctrine does not categorically exclude the foregoing acts, the District Court properly omitted the

proposed examples from the jury instructions.

        In any event, the Court’s actual instructions on Count One repeatedly emphasized the need for

the jury to find that the defendants acted in a deceitful or dishonest manner in order to convict. A VI:

419/6158 (“Only conduct that both is intended to impede the lawful functions of a government agency

and is fraudulent or dishonest will support a charge of conspiracy to defraud a government agency. . . .

Not all conduct that impedes the lawful functions of a government agency is illegal. To be unlawful,

that conduct has to entail fraud, deceit, or other dishonest means.”). “[V]iewing the charge as a whole,”

we find no prejudicial error. Aina-Marshall, 336 F.3d at 170.

                                B. Conscious Avoidance Instruction

         The defendants further argue that there was no factual basis for the conscious avoidance

instruction in connection with Counts Two and Three, the tax evasion charges. “‘A conscious

avoidance instruction permits a jury to find that a defendant had culpable knowledge of a fact when the

evidence shows that the defendant intentionally avoided confirming the fact.’” United States v. Quinones,




                                                    61
635 F.3d 590, 594 (2d Cir. 2011) (quoting United States v. Ferrarini, 219 F.3d 145, 154 (2d Cir. 2000)).39

A conscious avoidance instruction is appropriate only when (1) “a defendant asserts the lack of some

specific aspect of knowledge required for conviction,” and (2) “the appropriate factual predicate for the

charge exists, i.e., the evidence is such that a rational juror may reach the conclusion beyond a

reasonable doubt that the defendant was aware of a high probability of the fact in dispute and

consciously avoided confirming that fact.” United States v. Ferguson, 676 F.3d 260, 278 (2d Cir. 2011)

(quotation marks omitted). The Government need not choose between an “actual knowledge” and a

“conscious avoidance” theory. United States v. Kaplan, 490 F.3d 110, 128 n.7 (2d Cir. 2007).

           In this case, the Government requested a conscious avoidance instruction in connection with

the scienter element of Counts Two and Three, the tax evasion charges. The defense objected that

there was no factual predicate for the conscious avoidance instruction; the District Court overruled the

objection, finding unspecified “adequate evidence” to support the charge. The jury was instructed that

the knowledge element would be satisfied if a defendant “was aware of a high probability that a CDS

add-on shelter transaction lacked a reasonable possibility of a profit” and “acted with a conscious

purpose to avoid learning the truth about whether or not the shelter had a reasonable possibility of a

profit.”

           With respect to Coplan, we conclude that the conscious avoidance instruction was clearly

justified. In February 2001, Coplan reviewed and commented on a spreadsheet he received from Belle

Six that listed the Add-On clients and provided basic information about each client. That spreadsheet

reflected the cost of the client’s investment and the maximum potential payout ratio for the

investment—two of three data points necessary to evaluate profit potential. Specifically, the


39 We have recently noted that “[t]he Supreme Court appears to now prefer the appellation ‘willful blindness.’” United States

v. Ferguson, 676 F.3d 260, 278 n.16 (2d Cir. 2011) (quoting Global–Tech Appliances, Inc. v. SEB S.A., 131 S. Ct. 2060, 2070 &
n.9 (2011)). Because the parties used the term “conscious avoidance” below, we continue to use that term for purposes of
this case.

                                                             62
spreadsheet showed that the investment for each taxpayer cost approximately 0.5% of the desired tax

loss, and that the maximum payout ratio for each taxpayer was approximately 2:1 (profit to premium).

See note 25, ante (describing the 2:1 payoff ratio). From these two variables, it was apparent that Add-

On lacked profit potential if the fees exceeded 1.0%. Given Coplan’s role as the head of SISG and his

involvement in setting the Add-On fees, there was sufficient evidence to allow the jury to conclude

that, if Coplan did not have actual knowledge that the fees exceeded 1.0%, he “decided not to learn th[at]

key fact,” Rodriguez, 983 F.2d at 458. For that reason, we conclude that the conscious avoidance

instruction was appropriate with respect to Coplan.

            The factual basis for the conscious avoidance instruction as to Shapiro and Nissenbaum

presents a much closer question. Because we are reversing Counts Two and Three with respect to

Shapiro and Nissenbaum based on the insufficiency of the evidence, see Part II.B, ante, we need not, and

do not, reach their challenges to the conscious avoidance instruction.

                                         C. Economic Substance Instruction

             Finally, the defendants also argue that the instructions on Counts Two and Three contained an

improper definition of “economic substance.” The District Court instructed the jury that the Add-On

transaction lacked “economic substance” if (1) the transaction offered “no reasonable possibility that

the transaction would result in a profit,” and (2) the relevant taxpayer had “no business purpose” for

engaging in the transaction.40 The defendants challenge the “no reasonable possibility that the


40   With respect to the economic substance test, the District Court instructed the jury as follows:

                      In order to establish that a transaction lacks economic substance, the government must
            prove two elements beyond a reasonable doubt: The first element is that there was no reasonable
            possibility that the transaction would result in a profit. The second element is that the relevant
            taxpayer had no business purpose for engaging in the transaction in question apart from the creation
            of the tax deduction.

                     ....

                     Now, let me say a few words about your determination as to whether or not there was a
            reasonable possibility that the shelter would result in a profit. This element requires you to reach an
                                                                63
transaction would result in a profit” language in the first element of the instruction, arguing instead a

transaction lacks economic substance only where there is “no market risk.”

         As a general matter, a transaction that lacks economic substance will not provide the basis for a

tax deduction. Ferguson v. Comm’r, 29 F.3d 98, 101 (2d Cir. 1994). A transaction lacks economic

substance if it “can not [sic] with reason be said to have purpose, substance, or utility apart from [its]

anticipated tax consequences.” Lee v. Comm’r, 155 F.3d 584, 586 (2d Cir. 1998) (quotation mark

omitted); see also Jacobson v. Comm’r, 915 F.2d 832, 837 (2d Cir. 1990) (“A sham transaction analysis

requires a determination whether the transaction has any practicable economic effects other than the

creation of income tax losses.” (internal quotation marks omitted)).

         The law of economic substance, it must be said, is not a model of clarity. The economic

substance doctrine was, “if not formulated, then at least popularized” by Judge Learned Hand’s opinion

in Helvering v. Gregory, 69 F.2d 809 (2d Cir. 1934), aff’d, Gregory v. Helvering, 293 U.S. 465 (1935). David P.

Hariton, Sorting Out the Tangle of Economic Substance, 52 Tax Law. 235, 241 (1999). Since Gregory, the

economic substance doctrine “has been applied differently from circuit to circuit and sometimes

inconsistently within circuits.” Modern Tax Controversies, 957 Practicing Law Inst. at 478-35

(summarizing the “disjunctive, conjunctive, and unitary formulations” of the economic substance

doctrine).41



        objective judgment about whether the government has proved that there was no reasonable
        possibility that the shelter would result in a profit. In other words, this does not depend upon what
        the taxpayer believed about the profit potential. It requires you to consider all of the evidence and
        reach a conclusion about whether the government has proved beyond a reasonable doubt that there
        was no reasonable possibility of a profit on the tax shelter after the fees and other costs were paid. If
        you find that the government has proved beyond a reasonable doubt that there was no reasonable
        possibility of a profit, then you move on to the second element, whether the relevant taxpayer had no
        business purpose for engaging in the tax shelter. If you find that the government has not proved the
        lack of a reasonable possibility of a profit, then you must reject the government’s theory and find the
        defendants not guilty.
A VI: 424/6176–77 (paragraph breaks omitted).
41In 2010, Congress finally codified the economic substance doctrine at 26 U.S.C. § 7701(o). The codified version applies
prospectively to transactions entered into after March 30, 2010, and is therefore inapplicable to this case.
                                                             64
        Our Circuit is no exception. In United States v. Atkins, we approved an instruction that a

transaction lacks economic substance if it was subject to “no market risk.” 869 F.2d 135, 140 (2d Cir.

1989) (upholding a charge that the transaction at issue lacked economic substance if (1) it was “not

intended either to make or preserve any profit or to limit a loss in any way,” and (2) it was subject to no

market risk in that “changes in market prices cannot have any effect” (quotation marks omitted)). In

United States v. Regan, 937 F.2d 823, 827 (2d Cir. 1991), we suggested, without expressly ruling, that a

“no market risk” instruction was erroneous on the particular facts of that case. Most recently, in a non-

precedential disposition, we approved an instruction that a transaction lacks economic substance when

there is “no reasonable possibility that the transaction would result in a profit.” United States v. Pfaff, 407

F. App’x 506, 508 (2d Cir. 2010) (quotation marks omitted). In so holding, we noted that the

“narrower definition” we previously approved did not “state the outer limits of the economic substance

doctrine.” Id.

        Despite these inconsistencies, we return to the premise that a transaction lacks economic

substance if it “can not [sic] with reason be said to have purpose, substance, or utility apart from [its]

anticipated tax consequences.” Lee, 155 F.3d at 586 (emphasis added). Given the presence of the

reasonableness standard in our early formulations of the economic substance doctrine, we now hold

that the District Court’s “no reasonable possibility that the transaction would result in a profit”

instruction, see note 40, ante, accurately stated the law.

                                         IX. “Spillover” Prejudice

        Coplan argues that, should his conviction on Counts One, Two, Three, or Seven be overturned,

this Court would be obligated to vacate Count Five (obstruction of the IRS), based on “spillover

prejudice.” Because we affirm Coplan’s conviction in its entirety, we reject this argument. Vaughn




                                                       65
likewise argues that the allegedly improper venue on Count Six and the admission of the coconspirator

statements caused prejudicial spillover. We reject this argument, as we rejected its predicates.

                X. Procedural and Substantive Reasonableness of Bolton’s Sentence

        Finally, Bolton challenges the procedural and substantive reasonableness of his 15-month

sentence. As previously noted, Bolton pleaded guilty to a Superseding Information charging him in

one count of conspiracy, in violation of 18 U.S.C. § 371, with three objectives: (1) a Klein conspiracy; (2)

making false statements to the IRS; and (3) obstruction of the IRS. On appeal, Bolton contends that

(1) the District Court erred in concluding that his conviction under § 371 resulted in a “tax loss” within

the meaning of the Guidelines; (2) his sentence of 15 months of imprisonment was substantively

unreasonable; and (3) the $3 million fine imposed by the District Court should be vacated in light of

United States v. Pfaff, 619 F.3d 172 (2d Cir. 2010).

        We review a criminal sentence for “reasonableness,” which “amounts to review for abuse of

discretion.” United States v. Cavera, 550 F.3d 180, 187 (2d Cir. 2008) (en banc). “Reasonableness review

requires an examination of the length of the sentence (substantive reasonableness) as well as the

procedure employed in arriving at the sentence (procedural reasonableness).” United States v. Johnson,

567 F.3d 40, 51 (2d Cir. 2009). A district court commits procedural error where it fails to calculate (or

improperly calculates) the Guidelines range, treats the Guidelines as mandatory, fails to consider the §

3553(a) factors, selects a sentence based on clearly erroneous facts, or fails to adequately explain the

chosen sentence. Gall v. United States, 552 U.S. 38, 51 (2007). We have previously likened our review

for substantive unreasonableness “to the consideration of a motion for a new criminal jury trial, which

should be granted only when the jury’s verdict was ‘manifestly unjust,’ and to the determination of

intentional torts by state actors, which should be found only if the alleged tort ‘shocks the conscience.’”




                                                       66
United States v. Dorvee, 616 F.3d 174, 183 (2d Cir. 2010) (quoting United States v. Rigas, 583 F.3d 108,

122–23 (2d Cir. 2009)).

                                       A. Sentencing Proceedings

        The parties—the Government and Bolton, in this context—stipulated in the plea agreement

that “under the special facts of this case applicable to the defendant, there is no ‘tax loss’ as defined in

§ 2T1.1(c) of the Sentencing Guidelines.” Bolton A. 36. It was further stipulated that Bolton’s

advisory Guidelines range would be 0 to 6 months of imprisonment if the Court applied U.S.S.G.

§ 2T1.9, or 10 to 16 months of imprisonment if the Court applied U.S.S.G. § 2J1.2. The Pre-Sentence

Report of the U.S. Probation Office calculated an advisory Guidelines range of 0 to 6 months of

imprisonment under § 2T1.9 and recommended a sentence of 6 months of imprisonment. In its

sentencing submission, the Government agreed with the Probation Office that the applicable

Guidelines range was 0 to 6 months, but urged the Court to impose a sentence above that range based

on the factors set forth in 18 U.S.C. § 3553(a).

        By order dated January 29, 2010, Judge Stein ordered counsel to appear at a hearing in order to

discuss “several issues” related to Bolton’s Guidelines calculation. At that hearing, Judge Stein

explained that he had a “huge problem” with the parties’ stipulation that no tax loss was attributable to

Bolton under the Guidelines. Specifically, Judge Stein stated that he could not be “intellectually

honest” and adopt the position that there was no tax loss attributable to Bolton in light of his (Judge

Stein’s) conclusion that the tax loss attributable to the trial defendants exceeded $400 million. At the

April 13, 2010 sentencing hearing, Judge Stein applied § 2T1.1(a) and calculated an advisory Guidelines

range of 210 to 262 months of imprisonment based on an estimated tax loss in excess of $400 million.

He then imposed a sentence of 15 months of imprisonment, noting that “if my finding on loss is




                                                     67
incorrect, the sentence would still be the same because this is a substantial, massive departure.” Bolton

A 117.

                                            B. Procedural Unreasonableness

            Bolton argues on appeal that the District Court committed procedural error by applying

§ 2T1.1(a) even though he was not convicted of tax evasion. In essence, Bolton contends that a “tax

loss” within the meaning of the Guidelines exists only where a defendant willfully evaded taxes or

committed certain other “specific intent” crimes.

            The Guideline applicable to § 371 conspiracy convictions is § 2T1.9,42 which states that a

defendant’s base offense level shall be the greater of 10 or the offense level determined from § 2T1.1 or

§ 2T1.4, as appropriate. Section 2T1.1 is entitled “Tax Evasion; Willful Failure to File Return, Supply

Information, or Pay Tax; Fraudulent or False Returns, Statements, or Other Documents.”43 Section

2T1.4 is entitled “Aiding, Assisting, Procuring, Counseling, or Advising Tax Fraud.”44 Under either

provision, the base offense level is determined by calculating the “tax loss” for the offense.


42   Section 2T1.9 provides, in relevant part:

            Conspiracy to Impede, Impair, Obstruct, or Defeat Tax
            (a)   Base Offense Level (Apply the greater):
                    (1)    Offense level determined from § 2T1.1 or § 2T1.4, as appropriate; or
                    (2)    10.

U.S.S.G. § 2T1.9(a).

43   Section 2T1.1 provides, in relevant part:

            Tax Evasion; Willful Failure to File Return, Supply Information, or Pay Tax; Fraudulent or False Returns,
            Statements, or Other Documents
            (a)   Base Offense Level:
                    (1)     Level from § 2T4.1 (Tax Table) corresponding to the tax loss; or
                    (2)     6, if there is no tax loss.

U.S.S.G. § 2T1.1(a).

44   Section 2T1.4 provides, in relevant part:

            Aiding, Assisting, Procuring, Counseling, or Advising Tax Fraud
            (a)    Base Offense Level:
                     (1)     Level from § 2T4.1 (Tax Table) corresponding to the tax loss; or
                                                               68
         Pursuant to § 2T1.1(c)(1), a “tax loss” is defined as follows:

         If the offense involved tax evasion or a fraudulent or false return, statement or other
         document, the tax loss is the total amount of loss that was the object of the offense
         (i.e., the loss that would have resulted had the offense been successfully completed).

U.S.S.G. § 2T1.1(c)(1). The definition measures tax loss by reference to “the object of the offense.”

But nothing in the definition limits the existence of a “tax loss” to instances where a defendant acted

willfully or otherwise intended to cause a loss to the IRS. Thus, although the title of the provision

makes clear that § 2T1.1 is focused on tax evasion and other willful violations of the tax laws, nothing

in the language limits the application of § 2T1.1 to such crimes.45                    Assuming arguendo that the

District Court did err in applying § 2T1.1, that error would be harmless because the District Court

stated explicitly that it would impose the same sentence regardless of the loss amount. See United States

v. Jass, 569 F.3d 47, 68 (2d Cir. 2009) (“Where we identify procedural error in a sentence, but the record

indicates clearly that the district court would have imposed the same sentence in any event, the error

may be deemed harmless, avoiding the need to vacate the sentence and to remand the case for

sentencing.” (internal quotation marks omitted)). Bolton attempts to minimize the significance of the

District Court’s statements by characterizing them as “cursory” observations “near the close of Mr.

Bolton’s sentencing.” But nothing about the sentencing below was “cursory.” Although the Court

determined that the applicable Guidelines range was 210 to 262 months of imprisonment, it ultimately

imposed a sentence of 15 months—a 93% reduction from the low end of that range. Inasmuch as

Bolton’s sentence clearly was not driven by the initial Guidelines calculation, the Court’s statement that




                   (2)    6, if there is no tax loss.
For purposes of this guideline, the “tax loss” is the tax loss, as defined in § 2T1.1, resulting from the defendant’s aid,
assistance, procurance or advice.
U.S.S.G. § 2T1.1(a).

 We note, however, our considerable skepticism about the wisdom of applying an intended rather than actual loss measure
45

where, as here, the defendant has not been convicted of a crime requiring him to have the specific intent to cause a tax loss.
                                                               69
it would impose the same sentence even in the absence of a tax loss is amply supported by the record.

For that reason, we can “confidently conclude” that any arguable error here was harmless. Id.

                                    C. Substantive Unreasonableness

          Bolton also argues that his 15-month sentence was substantively unreasonable because the

District Court “unreasonably weighted the seriousness of [his] offense based on the evidence,

particularly in comparison to the E&Y defendants.”46 Bolton Br. 28. But given the fact that Bolton

played a significant and necessary role in the conspiracy (by coming up with the Add-On cover story

and signing IRS documents, for example), as well as his significant financial gain in implementing the

transactions, it cannot be said that his 15-month sentence was “manifestly unjust.” See Rigas, 583 F.3d

at 122.

                                        D. Fine Imposed on Bolton

          Finally, Bolton argues—and the Government agrees—that the $3 million fine imposed by the

District Court should be vacated in light of United States v. Pfaff, 619 F.3d 172 (2d Cir. 2010), which was

decided four months after Bolton’s sentencing. In Pfaff, we held that, in the absence of a jury finding, a

district court may not impose a fine greater than the default statutory maximums provided by 18 U.S.C.

§ 3571(d). Id. at 175 (“[I]t is the clear implication of Apprendi and Blakely that when a jury does not

make a pecuniary gain or loss finding, § 3571’s default statutory maximums cap the amount a district

court may fine the defendant.”). Further, in the time period between the sentencing hearing in this case

and the filing of this opinion, the Supreme Court decided Southern Union Co. v. United States, squarely

holding that “the rule of Apprendi applies to the imposition of criminal fines.” 132 S. Ct. 2344, 2357

(2012) (Sotomayor, J.).




46The sentences of the trial defendants were as follows: Robert Coplan (36 months), Martin Nissenbaum (30 months),
Richard Shapiro (28 months), Brian Vaughn (20 months).
                                                       70
        It is indisputable that the District Court could not impose a fine in excess of the statutory

maximum of $250,000. See 18 U.S.C. § 3571(b)(3). Accordingly, we vacate the portion of Bolton’s

sentence that imposed the fine, and remand the cause to the District Court for the sole purpose of

reducing the fine to the statutory maximum of $250,000.

                                            CONCLUSION

        The District Court presided over this complex and difficult case with admirable care and

understanding of its intricacies.

        To summarize, we hold that:

        (1)   The defendants’ challenge to the so-called Klein conspiracy theory of criminal liability

              under 18 U.S.C. § 371 fails under the law of the Circuit, which remains good law absent

              review or modification by the Supreme Court;

        (2)   With respect to the sufficiency challenges:

                a. The convictions of Shapiro and Nissenbaum on Count One, charging conspiracy in

                    violation of 18 U.S.C. § 371, are REVERSED due to insufficient evidence;

                b. The convictions of Shapiro and Nissenbaum on Counts Two and Three, charging

                    tax evasion in violation of 26 U.S.C. § 7201, are REVERSED due to insufficient

                    evidence;

                c. Nissenbaum’s conviction on Count Four, charging him with obstruction of the IRS

                    in violation of 26 U.S.C. § 7212, is REVERSED due to insufficient evidence;

        (3)   Venue was proper with respect to Count Six, which charged Vaughn with false statements

              to the IRS in violation of 18 U.S.C. § 1001;

        (4)   The District Court did not err by admitting the testimony of Graham Taylor;




                                                    71
       (5)   The District Court did not err by admitting the out-of-court statements of the alleged

             coconspirators;

       (6)   The District Court did not err by excluding portions of Coplan’s and Vaughn’s deposition

             transcripts;

       (7)   There was no prosecutorial misconduct in the Government’s rebuttal summation;

       (8)   The District Court did not err by:

                 a. declining to give a “theory of the defense” instruction;

                 b. including a conscious avoidance instruction; or

                 c. instructing the jury that “economic substance” existed only if there was a

                     “reasonable possibility” of profit;

      (9)    Spillover prejudice did not infect the remaining convictions; and

      (10)   The portion of Bolton’s sentence imposing a fine is VACATED and the cause is

             REMANDED for the sole purpose of reducing the fine to the statutory maximum of

             $250,000.

      In light of these holdings, the judgments of conviction of Coplan and Vaughn are AFFIRMED,

the judgments of conviction of Shapiro and Nissenbaum are REVERSED, and the portion of

Bolton’s sentence imposing a $3 million fine VACATED and the cause is REMANDED for the sole

purpose of reducing the fine to the statutory maximum of $250,000. Judgment with respect to

defendants Shapiro and Nissenbaum shall enter on all counts as to which we have reversed the

judgment of the District Court.




                                                   72
                                    APPENDIX A


   United States v. Robert Coplan, Martin Nissenbaum, Richard Shapiro & Brian Vaughn
                                     07 Cr. 453 (SHS)
                                   Redacted Indictment
                                    [Source: A. 90-143.]

Count                     Title                     Statute               Defendants
Count 1                Conspiracy               18 U.S.C. § 371       Coplan, Nissenbaum,
                                                                        Shapiro, Vaughn
                       Objectives:
                    Klein conspiracy;
                     Tax Evasion;
                    False Statements
Count 2               Tax Evasion               26 U.S.C. § 7201;     Coplan, Nissenbaum,
                   [Client: LaRocque]             18 U.S.C. § 2         Shapiro, Vaughn
Count 3               Tax Evasion               26 U.S.C. § 7201;     Coplan, Nissenbaum,
                 [Client: Cornerstone]            18 U.S.C. § 2         Shapiro, Vaughn
Count 4            Obstruction of the           26 U.S.C. § 7212          Nissenbaum
                         IRS
Count 5            Obstruction of the           26 U.S.C. § 7212             Coplan
                         IRS
Count 6           False Statements to           18 U.S.C. § 1001             Vaughn
                        the IRS
Count 7           False Statements to           18 U.S.C. § 1001             Coplan
                        the IRS

                             United States v. Charles Bolton
                                  07 Cr. 453 (SHS)
                              Superseding Information
                              [Source: Bolton A. 28-34.]

Count                     Title                     Statute                Defendant
Count 1                Conspiracy               18 U.S.C. § 371              Bolton




                                           73
                                            APPENDIX B

                            RELEVANT STATUTORY PROVISIONS

18 U.S.C. § 371—Conspiracy to Commit Offense or to Defraud United States

       If two or more persons conspire either to commit any offense against the United States, or to
defraud the United States, or any agency thereof in any manner or for any purpose, and one or more of
such persons do any act to effect the object of the conspiracy, each shall be fined under this title or
imprisoned not more than five years, or both.

       If, however, the offense, the commission of which is the object of the conspiracy, is a
misdemeanor only, the punishment for such conspiracy shall not exceed the maximum punishment
provided for such misdemeanor.

26 U.S.C. § 7201—Attempt to Evade or Defeat Tax

         Any person who willfully attempts in any manner to evade or defeat any tax imposed by this
title or the payment thereof shall, in addition to other penalties provided by law, be guilty of a felony
and, upon conviction thereof, shall be fined not more than $100,000 ($500,000 in the case of a
corporation), or imprisoned not more than 5 years, or both, together with the costs of prosecution.

26 U.S.C. § 7212—Attempts to Interfere with Administration of Internal Revenue Laws

(a) Corrupt or forcible interference

         Whoever corruptly or by force or threats of force (including any threatening letter or
communication) endeavors to intimidate or impede any officer or employee of the United States acting
in an official capacity under this title, or in any other way corruptly or by force or threats of force
(including any threatening letter or communication) obstructs or impedes, or endeavors to obstruct or
impede, the due administration of this title, shall, upon conviction thereof, be fined not more than
$5,000, or imprisoned not more than 3 years, or both, except that if the offense is committed only by
threats of force, the person convicted thereof shall be fined not more than $3,000, or imprisoned not
more than 1 year, or both. The term “threats of force”, as used in this subsection, means threats of
bodily harm to the officer or employee of the United States or to a member of his family.

(b) Forcible rescue of seized property

        Any person who forcibly rescues or causes to be rescued any property after it shall have been
seized under this title, or shall attempt or endeavor so to do, shall, excepting in cases otherwise
provided for, for every such offense, be fined not more than $500, or not more than double the value
of the property so rescued, whichever is the greater, or be imprisoned not more than 2 years.




                                                   74
18 U.S.C. § 1001—Statements or Entries Generally

(a) Except as otherwise provided in this section, whoever, in any matter within the jurisdiction of the
executive, legislative, or judicial branch of the Government of the United States, knowingly and
willfully—

        (1) falsifies, conceals, or covers up by any trick, scheme, or device a material fact;
        (2) makes any materially false, fictitious, or fraudulent statement or representation; or
        (3) makes or uses any false writing or document knowing the same to contain any materially
             false, fictitious, or fraudulent statement or entry;

shall be fined under this title, imprisoned not more than 5 years or, if the offense involves international
or domestic terrorism (as defined in section 2331), imprisoned not more than 8 years, or both. If the
matter relates to an offense under chapter 109A, 109B, 110, or 117, or section 1591, then the term of
imprisonment imposed under this section shall be not more than 8 years.

(b) Subsection (a) does not apply to a party to a judicial proceeding, or that party’s counsel, for
statements, representations, writings or documents submitted by such party or counsel to a judge or
magistrate in that proceeding.

(c) With respect to any matter within the jurisdiction of the legislative branch, subsection (a) shall apply
only to—

        (1) administrative matters, including a claim for payment, a matter related to the procurement
            of property or services, personnel or employment practices, or support services, or a
            document required by law, rule, or regulation to be submitted to the Congress or any office
            or officer within the legislative branch; or
        (2) any investigation or review, conducted pursuant to the authority of any committee,
            subcommittee, commission or office of the Congress, consistent with applicable rules of the
            House or Senate.




                                                    75
USA v. Coplan, No.
10-0583-cr(L)




      1       KEARSE, Circuit Judge, dissenting in part:

      2                      I respectfully dissent from so much of the Majority Opinion as finds the evidence

      3       insufficient to support (1) the convictions of defendants Richard Shapiro and Martin Nissenbaum of

      4       conspiracy, in violation of 18 U.S.C. § 371, to (a) defraud the United States by impairing the lawful

      5       functions of an agency of the United States government, to wit, the Internal Revenue Service ("IRS"),

      6       (b) commit tax evasion, see 26 U.S.C. § 7201, and (c) make false statements to the IRS, see 18 U.S.C.

      7       § 1001 (Count One); and (2) those two defendants' convictions of attempted tax evasion in violation

      8       of 26 U.S.C. § 7201 (Counts Two and Three).

      9                      As the Majority Opinion sets out, this prosecution focused principally on

     10                      the design, implementation, and audit defense of four tax shelters developed
     11                      by the [Ernst & Young LLP ("E&Y")] VIPER Group/SISG: the (1)
     12                      Contingent Deferred Swap ("CDS"); (2) Currency Options Bring Reward
     13                      Alternatives ("COBRA"); (3) CDS Add-On ("Add-On"); and (4) Personal
     14                      Investment Corporation ("PICO") shelters.

     15       Majority Opinion ante at 4. "The IRS can disallow deductions resulting from a transaction that 'can

     16       not [sic] with reason be said to have purpose, substance, or utility apart from [its] anticipated tax

     17       consequences. Such transactions are said to lack "economic substance."'" Majority Opinion ante

     18       at 10 n.15 (quoting, with alterations, Lee v. Commissioner, 155 F.3d 584, 586 (2d Cir. 1998)).
 1                   Count One of the superseding indictment alleged that each of the above four tax

 2   shelters, along with one other, was fraudulent, and that Shapiro, Nissenbaum, and defendant Robert

 3   Coplan--each of whom was a lawyer with a Master's Degree in tax law and decades of experience in

 4   tax practice--and other persons known and unknown, conspired and agreed to defraud the United

 5   States, to violate the federal income tax laws, and to make false statements to the IRS. As the

 6   Majority Opinion acknowledges, the evidence as to the conspiracy's objectives is not deficient if there

7    is sufficient evidence of at least one of the alleged objectives. See Majority Opinion ante at 18.

8    "[T]he Government sought to demonstrate that the defendants hid the truth from the IRS by

9    withholding information and making affirmative misstatements" about these shelters, Majority

10   Opinion ante at 10, in IRS audit interviews and in connection with a 2000 IRS amnesty program that

11   would allow a person who had invested in tax shelters, if the IRS deemed them not legitimate

12   transactions, to avoid paying penalties on those transactions.

13                   The Majority does not suggest that there was insufficient evidence for the jury to find

14   that there existed a conspiracy with one or more of the objectives alleged in Count One. Nor could

15   it, given that Coplan and defendant Brian Vaughn, a certified public accountant and certified financial

16   planner employed by E&Y, were convicted of participating in the alleged conspiracy and that we

17   affirm those convictions. Rather, the Majority finds that the evidence was insufficient to show that

18   Shapiro and Nissenbaum knew of the conspiracy and participated in it. See Majority Opinion ante

19   at 18-19.

20                   The Majority Opinion sets out the well established legal principles that "[i]n the

21   context of a conspiracy conviction, 'deference to the jury's findings is especially important . . . because

22   a conspiracy by its very nature is a secretive operation, and it is a rare case where all aspects of a


                                                         2
 1   conspiracy can be laid bare in court,'" Majority Opinion ante at 18 (quoting United States v. Rojas,

 2   617 F.3d 669, 674 (2d Cir. 2010)); that "'the government is entitled to prove its case solely through

3    circumstantial evidence,'" Majority Opinion ante at 29 (quoting United States v. Rodriguez, 392 F.3d

4    539, 544 (2d Cir. 2004)); and that "[i]n evaluating a sufficiency challenge, we 'must view the evidence

5    in the light most favorable to the government, crediting every inference that could have been drawn

6    in the government's favor, and deferring to the jury's assessment of witness credibility and its

 7   assessment of the weight of the evidence.'" Majority Opinion ante at 17 (quoting United States v.

 8   Chavez, 549 F.3d 119, 124-25 (2d Cir. 2008)). But in finding the evidence insufficient to permit the

 9   jury to infer that Shapiro and Nissenbaum knew of the conspiracy and participated in it, the Majority

10   does not apply these principles.



11   A. The Conspiracy Count

12                  E&Y, an accounting firm, had a Personal Financial Counseling group ("PFC") that

13   included a group, initially called VIPER--an acronym for Value Ideas Produce Extraordinary Results--

14   and whose name was later changed to Strategic Individual Solutions Group ("SISG") (see

15   Government Exhibit ("GX") 73), which marketed tax shelters (see Trial Transcript ("Tr."), 4619,

16   1069). Coplan was the leader of this "high net worth market group" (Tr. 4619-20); Shapiro and

17   Nissenbaum were core members (see, e.g., id. at 2135-37, 2236).

18                  At trial, the government introduced numerous e-mails between or among Shapiro,

19   Nissenbaum, and Coplan (and others) discussing, inter alia, the need to prevent certain materials,

20   which mentioned E&Y clients' interest in minimizing or eliminating taxes, from falling into the hands

21   of the IRS. These included:


                                                       3
 1   - GX 795 (Coplan e-mail dated November 27, 2000, with copies to Shapiro, among
 2   others, stating, "we refrain from sending out--or leaving with a client--promotional
 3   materials that go through the steps of a strategy, or even highlight the tax benefits of
 4   a strategy. Business purpose is a critical element to prove for these solutions, and the
 5   less evidence there is that the client responded to a tax-saving promotion, the better
 6   for his argument that there were non-tax motivations guiding his actions." (emphasis
 7   added));

 8   - GX 860 (Shapiro e-mail dated May 22, 2001, to Melinda Merk, a member of the PFC
 9   group who worked with SISG (see Tr. 1281), stating that "as a general rule,
10   presentation materials SHOULD NOT be left with the client. Clients may take notes,
11   etc., but materials should be handed back at the end of the meeting. In an audit
12   meeting i [sic] had in Minneapolis on a COBRA transaction, one of the items
13   requested of the taxpayer was any promotional materials that they had.");

14   - GX 795 (Merk e-mail dated November 22, 2000, to an E&Y tax department
15   employee stating "I am hesitant to prepare and provide any summary for delivery to
16   a potential client, based on my recent conversations with Richard Shapiro and Bob
17   Coplan that we be very careful about providing such information in writing for
18   potential dissemination into the marketplace and/or receipt by the media, Treasury
19   . . . ." (emphases added));

20   - GX 555 (Coplan e-mail dated July 17, 2001, to some 60 E&Y employees, including
21   Shapiro and Nissenbaum, "instruct[ing them] to immediately delete and dispose of any
22   and all materials in [their] drawers and on [their] computers related to the COBRA
23   transaction other than" opinion letters and documents related to the client's currency
24   trades and "documents supporting the economic purpose and bona fide nature of the
25   investment in the transaction" (emphases added));

26   - GX 602 (Coplan e-mail dated July 23, 2001, to some 60 E&Y employees, including
27   Shapiro and Nissenbaum, re "PICO Materials Leak," stating that a potential client had
28   sent a set of E&Y's PICO materials to an E&Y competitor, and that although Coplan
29   was "not suggesting that this is necessarily a calamitous event[, t]he potential negative
30   repercussions are obvious, and a fax of the materials to certain people [including] the
31   government WOULD have calamitous results" (emphasis added)); and

32   - GX 639 (Coplan e-mail dated June 14, 2000, to an E&Y regional senior manager,
33   with a copy to Shapiro re "Final Set of CDS Add-On Slides," stating, inter alia, that
34   "[i]f these slides ever made their way to the IRS . . . the entire business purpose
35   argument that gives us the ability to distinguish this from COBRA would be out the
36   window." (emphases added)).




                                                4
 1                  As discussed below in subparts 1-4 and Part B below, the government also presented

 2   testimony from many witnesses, including

 3          - former E&Y tax partner Thomas A. Dougherty, who testified that, in the presence
 4          of Shapiro and others, he lied to the IRS in connection with the COBRA tax shelter,
 5          making false but "plausible" representations that he had discussed with Shapiro;

 6          - former E&Y client Kathryn Munro, who testified to statements made--and statements
 7          not made--to her by E&Y in connection with investments in CDS and Add-On
 8          shelters, and with respect to false and misleading amnesty letters prepared by E&Y for
 9          submission to the IRS;

10          - former E&Y manager Jason Bryant Rydberg, who dealt with Munro and testified to,
11          inter alia, the preparation of false and misleading opinion letters and letters to the IRS
12          following its offer of amnesty with regard to CDS and Add-On tax shelters, and
13          testified to the E&Y requirement that presentations with regard to those shelters be
14          shown in advance to Shapiro;

15          - former E&Y manager Belle Six--who earned a total of some $22 million in
16          commissions both from selling CDS shelters while at E&Y working with, among
17          others, Shapiro, Coplan, and Nissenbaum, and from selling E&Y Add-On shelters
18          thereafter--who had pleaded guilty to conspiring to defraud the government and had
19          been required to pay or forfeit that total to the government (see Tr. 2106-10); and

20          - former practicing lawyer Peter Cinquegrani, who had pleaded guilty to, inter alia,
21          conspiring with others to give false statements and false documents to the IRS in
22          connection with the PICO tax shelter, having collaborated with Shapiro in fashioning
23          PICO opinion letters that Cinquegrani testified he knew contained false and
24          misleading statements constituting a "cover story" (Tr. 4015).



25          1. Shapiro and COBRA

26                  Shapiro was the E&Y leader on the national roll-out presentation of the COBRA tax

27   shelter in 1999. (See Tr. 4588.) Dougherty testified principally about the professed--and purported--

28   interests of three members of a partnership called WRB Lake who invested in a COBRA tax shelter.

29   Dougherty had been instructed by E&Y's tax division director to ask two of those partners--E&Y

30   clients Bill Wanner and Brian Sullivan, whose business was water purification and desalinization and

                                                        5
 1   who were selling a company at a profit of more than $20 million each--whether they were interested

 2   in E&Y's CDS strategy (see id. at 1081-86) to convert their ordinary income, which would have been

 3   taxable at about a 40% rate, into long-term capital gains, which would be taxable at 20% (see

 4   generally id. at 2149). However, Wanner and Sullivan, along with another WRB Lake partner,

 5   informed Dougherty that they were interested instead in a strategy whereby taxes on their transaction

 6   would be not just minimized but "eliminate[d]." (Id. at 1087.) After E&Y decided to market

 7   COBRA, its tax elimination strategy (see id. at 1088-89), the WRB Lake partners sought "to enter into

 8   a COBRA transaction . . . for the purpose of eliminating tax on the transaction they were going

 9   through"; the clients said they "w[ere] interested in pursuing [COBRA] for that purpose" (id. at 1183),

10   and in 1999 they did so. From the outset, Wanner had stated his "desire to enter into the COBRA

11   transaction for purposes of creating a tax loss." (Id. at 1141.)

12                  In mid-March 2001, Sullivan received notice from the IRS that the WRB Lake

13   partnership was being audited. He so informed Dougherty, who in turn informed Coplan by e-mail

14   and fax, which Coplan forwarded to, among others, Shapiro, Nissenbaum, and Denis Conlon (see

15   Tr. 1171-75), a member of E&Y's national tax practice whose specialty was responding to contacts

16   from the IRS (see GX 540; Tr. 1175-76). In a conference call in early April, Dougherty discussed

17   with Coplan and Conlon the "facts that could hurt the client's [sic] case" (Tr. 1186). Dougherty,

18   Coplan, and Conlon "tr[ied] to . . . come up with some ideas that may be presented to the [IRS] agent

19   for why the[]" WRB Lake partners entered the COBRA transaction (id. at 1182 (emphases added)),

20   even though Dougherty, Coplan, and Conlon "knew that this was a COBRA transaction, one all three

21   principals had entered into . . . to realize the tax savings" (id. at 1181). Dougherty testified:

22                  At this point of the discussion, we're looking at other reasons that the taxpayers
23                  came together for the purposes of why did they purchase foreign digital

                                                        6
 1                  contracts, why did they do this together in a partnership, and why did they
 2                  decide to terminate that partnership and not do any more foreign currency
 3                  investing.

 4   (Id.) Dougherty advanced various possible explanations, including that Wanner had had some prior

 5   experience, in his business, of doing some foreign currency trading, and "maybe that was something

6    we could throw out as being the fact supporting a reason for entering into this transaction" (id. at 1182

 7   (emphasis added)), although Wanner had not indicated to Dougherty any such motivation (see id.

 8   at 1181-83). Dougherty "also talked about the fact that the three [WRB Lake partners] happened to

 9   be joint investors in [a] newly formed company," which could explain why "they would be willing

10   to form a partnership together and carry on some partnership investment activities. Maybe that would

11   be something we could use." (Id. at 1182 (emphasis added).) Dougherty had already told Coplan and

12   Conlon "the real history behind these clients; that is, how they came to Ernst & Young and the

13   COBRA transaction." (Id. at 1736.) "They knew those facts about the three clients." (Id. at 1738.)

14   "We were talking about plausible reasons that could be presented"; "we needed to come up with some

15   business reasons why the transaction took place in the form it took place." (Id. at 1740 (emphases

16   added).)

17                  After that conference call among Dougherty, Coplan, and Conlon, Conlon sent

18   Dougherty and Coplan an e-mail dated April 19, 2001, stating that they needed to have Shapiro join

19   the thinking (see GX 542 ("I think we need Richard . . . . I want to state our case clearly and correctly

20   from the beginning . . . . IRS would like to catch us cold and get admissions that will hurt our case.

21   We need to make sure that does not happen.")). Accordingly, on April 20, 2001, Coplan e-mailed

22   Dougherty, Conlon, and Shapiro to schedule a conference "call with all of us . . . to go over the facts

23   of this case and plan how we will approach the agents on this matter." (Tr. 1188.)


                                                        7
 1                  In late April, a conference call was held among Dougherty, Coplan, Conlon, and

 2   Shapiro. During that call, Shapiro raised the question of business purpose (see Tr. 1741-42), saying

 3   "[w]e need to discuss business purpose on this transaction" (id. at 1191). Dougherty, however,

 4   "[h]ad" already "told Mr. Shapiro at that point the real facts about how these clients had come to Ernst

 5   & Young for the COBRA transaction." (Id. at 1741 (emphasis added).) The reason Dougherty,

 6   Coplan, Conlon, and Shapiro were "discussing business purpose" was the "same reason" that

 7   Dougherty, Coplan, and Conlon had discussed possible business purposes in their earlier call: they

 8   needed "to talk about the other reasons, plausible reasons, that could be discussed . . . should it

 9   become important to discuss that at the meeting with the agent." (Id. (emphases added).)

10                  Dougherty testified that in the ensuing May 17, 2001 IRS interview, attended by

11   Dougherty, Conlon, and Shapiro, Dougherty "lied" to the IRS agent "about why the three [WRB Lake

12   partners] got into the COBRA transactions." (Tr. 1743.) Dougherty gave the agent "the plausible

13   reasons that we had talked about during the discussions, which were misleading the agent as to the

14   real purpose." (Id. at 1743-44 (emphases added).) Dougherty testified that the "[s]tatements [he]

15   made to the agent about why the clients had done this, were . . . things [he] had gone over during the

16   calls with Mr. Coplan, Mr. Conlon, and Mr. Shapiro." (Id. at 1743 (emphasis added).)

17                  From this series of events alone, the jury could permissibly find that, with respect to

18   COBRA, Shapiro knowingly joined and participated in the conspiracy with Coplan and others to

19   impair the lawful functions of the IRS and to make false statements to the IRS.




                                                        8
1           2. Shapiro and CDS and CDS Add-On

2                   In addition, Shapiro was E&Y's "subject matter expert"--or "SME"--on its CDS

3    strategy (Tr. 4555), which would convert high ordinary income into long-term capital gains (taxable

4    at about half the rate of such ordinary income), and on the Add-On strategy (see GX 636), which,

5    when used in the second year of a CDS transaction, would involve the creation and liquidation of an

6    LLC and eliminate even the capital gains. The SME had the "technical expertise" (Tr. 4876), i.e., he

 7   "was the person that knew the transaction the best and that's who you went to for the questions" (id.

 8   at 4555) and "for approval" (id.). For example, a regional senior manager sent an e-mail to Shapiro

 9   forwarding a Power Point presentation to Shapiro "for approval as the CDS SME." (GX 30, dated

10   October 22, 1999.) And in response to a Power Point presentation proposed by Vaughn for Add-On,

11   Coplan stated that "the Add-On strategy will lose all of its 'business purpose' if it is reduced to steps

12   in a PowerPoint slide. The tax objective will appear to be the driving force" (GX 636 (Coplan e-mail

13   dated June 14, 2000, to Vaughn, with a copy to Shapiro)); Coplan recommended not using slides and

14   recommended that all "materials like this" should be reviewed in advance by Shapiro, as the Add-On

15   "SME" (id.).

16                  Success of the CDS shelter--involving a partnership that was to engage in swap

17   transactions purportedly having a term of 18 months--depended on the swap's termination after one

18   year but short of the 18-month stated termination date. One year was the dividing line between short-

19   term capital gains and long-term capital gains; termination prior to the end of the stated 18-month

20   term was required for gains to be treated as capital gains rather than ordinary income. (See, e.g.,

21   Tr. 2198-99.) Shapiro repeatedly urged that the fact that early termination was pre-planned not be

22   disclosed. On February 8, 2000, he sent an e-mail to Merk, with copies to Nissenbaum, Coplan, and


                                                        9
 1   Vaughn, on "the [CDS] action plan"; in addition to suggesting that he, Shapiro, along with Coplan

 2   or Vaughn, should be involved in any CDS sales contact, Shapiro noted "the fact that our swap will

 3   be terminated early"--and noted that this was "[c]learly . . . necessary for the flow of the transaction"--

 4   and he "question[ed] . . . seriously" whether there "should . . . be a document in existence . . . that has

 5   all chapters and verses laid out." (GX 66 (emphases added).) Shapiro added that "[t]he fact that no

 6   materials are to be left behind at a sales call is not enough. In my opinion, before anything is in 'stone'

 7   here, we should consider what are [sic] record will/should look like." (Id. (emphasis added).) And

 8   in an e-mail to Vaughn about "cds models," with copies to Nissenbaum, Coplan, and others, Shapiro

 9   instructed that certain "deletions" from the model documents were "essential," and that the statements

10   that "'Calculations assume utilization of the Early Termination Provision . . .' should be deleted."

11   (GX 100, dated April 14, 2000.)

12                   Bolton Capital Planning ("Bolton" or "BCP") was the general partner in some LLPs

13   created for CDS shelters. (See, e.g., Tr. 2215-16, 2477; GX 1231.) After Bolton received an inquiry

14   from the IRS with regard to a CDS shelter, Coplan revised the language of the initial draft of the BCP

15   response to the IRS inquiry to state that "[i]f the general partner, based on market fluctuations,

16   terminates the swap contracts early, capital gain would arise on such termination" (GX 412 (Coplan

17   e-mail dated January 18, 2001 (emphasis added))). Six testified that this "does not" (Tr. 2321)

18   "accurately describe what . . . clients" were "told . . . about early termination and how the decision was

19   made to early terminate" the CDS swaps (id. at 2320). The decision was not to be made based on

20   market fluctuations; the "understanding" was "[t]hat we assumed we would terminate, early terminate

21   . . . if the counterparty did not." (Id. at 2321 (emphases added).) The revised language in GX 412 had

22   been introduced the previous day in an e-mail from Coplan to Shapiro, Nissenbaum, and others, with


                                                         10
 1   the statement that "This one should be more acceptable to Richard." (GX 932, dated January 17,

 2   2001; see Tr. 2318-22.)

 3                  Consistent with Shapiro's observation that "early" termination was necessary for

 4   success of the CDS strategy but should not be so described, former E&Y client Munro testified that

 5   when she and her husband had invested in a CDS shelter, they were not told that the swap had a

 6   duration of 18 months. They were simply told it would last a year. (See Tr. 3548; see also id. at 4564

 7   (Rydberg testifying that "the maturity date of the swap that[ was] used in the CDS transaction" was

 8   18 months; "[w]e told [clients] it would last 12 months and a day to the early termination date"); id.

 9   at 4537 ("all the CDS transactions ha[d] the same . . . early termination date" of "12 months and one

10   day").)

11                  Munro also testified that the "purpose of [the Munros' CDS] transaction was to defer

12   [their] tax liability until [they] sold" shares that her husband had received from the exercise of stock

13   options "and could pay the capital gains tax." (Tr. 3539; see also id. at 3525, 3530-32.) In 1999 with

14   respect to CDS and in 2001 with respect to Add-On, Rydberg sent the Munros "representation

15   letter[s]" to sign and return in order to receive opinions from a law firm as to the legitimacy of their

16   investments in CDS and Add-On. (Id. at 3519-24, 4637-38.) Munro testified that these were letters

17   that she did "[n]ot really" read before signing (id. at 3524), having "paid a lot of money to Ernst &

18   Young for tax advice" (id. at 3526; see, e.g., id. at 4581 (Rydberg testifying that he told clients "the

19   fee[] for th[e CDS] transaction . . . was 4 percent of the loss that was being generated"); id. at 3512

20   (the Munros, for their CDS transaction, paid E&Y $400,000)). Munro testified that the representation

21   letters were false and misleading in that they misstated the purpose for which she and her husband had

22   invested in CDS and Add-On; and the opinion letters received by the Munros--who did not deal with

23   the opining law firm except through E&Y--repeated those misstatements. (See id. at 3524-41.)

                                                       11
 1                  Munro testified that, contrary to the E&Y-drafted representation letters, "[w]e did not

 2   invest in [the partnership] as a sound financial investment. We invested in it so we could pay less in

 3   taxes. That was the basic purpose of the transaction." (Tr. 3525.) Contrary to the representation

 4   letters, "[i]t wasn't a sound coherent business strategy. It was a specific transaction to help us reduce

 5   our taxes"; nobody "from Ernst & Young talk[ed] to [Munro] about a coherent business philosophy

 6   in connection with the CDS transaction." (Id.) Contrary to the opinion letters--which were based on

 7   the representation letters--the CDS in fact "had a predetermined outcome . . . and the outcome was

 8   the conversion of ordinary income to capital gains income. And that's what the purpose of the

 9   transaction was about." (Id. at 3530-31.) Contrary to the opinion letters, the partnership formed by

10   Munro and her husband for the CDS had no "overall business plan"; "[t]he plan of the partnership was

11   to convert ordinary income that you had by exercising your options and convert it to capital gain. So

12   pay less in taxes was the primary purpose of the partnership." (Id. at 3531-32.)

13                  In 2002, Rydberg informed Munro of the IRS's amnesty program, and E&Y drafted

14   amnesty letters for Munro and her husband with respect to CDS and Add-On, which were signed by

15   the Munros and were submitted to the IRS. (See Tr. 3545-46, 3550.) Munro testified that those

16   amnesty letters--which were based on the opinion letters and (a) described business purposes that the

17   Munros did not have, (b) did not mention the Munros' purpose of reducing taxes, and (c) stated that

18   the letters did not omit any material facts (see id. at 3546 (describing GX 1231 as pertaining to CDS

19   and GX 1232 as pertaining to Add-On))--were false and misleading (see Tr. 3544-50).

20                  The Munros' amnesty letters to the IRS, submitted in March 2002, had been drafted

21   by Rydberg. Rydberg testified that his draft for Add-On followed a template received from Coplan.

22   (See, e.g., Tr. 4657-58; GX 491.) Drafts of that template had been e-mailed by Coplan to, among

23   others, Shapiro and Nissenbaum on February 27, 2002 (see GX 490), and on March 5, 2002 (see

                                                        12
 1   GX 491). In the latter e-mail, Coplan stated "Please look this over to see if there are any changes you

 2   would make either to avoid unnecessary facts or to make it easier to complete accurately. I want to

 3   post this and distribute this morning. I will be sending along the CDS template later this morning

 4   . . . ." (Id.) Nissenbaum responded to Coplan, with a copy to Shapiro, that, other than believing

 5   details as to the specific option trades to be unnecessary, "[t]he disclosure looks fine to me" (id.; see

6    Tr. 4663); and Shapiro provided some nonsubstantive comments that were adopted (see Tr. 4663-65;

 7   compare GX 491 with GX 492). But "[t]hroughout these various drafts of the generic add-on amnesty

 8   template, . . . the basic description of the transaction remain[ed] the same" (id. at 4665); and those

 9   drafts omitted mention of tax-minimization or tax-elimination purposes (see GX 490, 491).

10                  Although the Add-On strategy for CDS was the brainchild of Vaughn (see

11   Tr. 2378-79), Add-On was in reality a combination of CDS and COBRA (see id. at 1378-81). Both

12   of the latter were shelters promoted to E&Y by Shapiro (see id. at 2144-46 (CDS); id. at 4588

13   (COBRA)), and Shapiro was the SME for Add-On (see GX 636). Vaughn, in a June 9, 2000 e-mail

14   to numerous E&Y tax department employees, with copies to Shapiro, Coplan, and Nissenbaum, noted

15   that "[w]ith the add-on feature, CDS can now be applied to capital gain situations," and stated that

16   "the 1999 and 2000 clients that have completed a CDS transaction" would shortly be "notif[ied] . . .

17   of the opportunity to participate in the new trading program." (GX 633.) Shapiro responded: "i [sic]

18   remain concerned of the formal pre-wired tie-in to cobra. i [sic] think it adversely impacts the story

19   that we can tell regarding the purpose of the transaction." (Id. (emphasis added).) Coplan then edited

20   the letter to be sent to clients announcing Add-On and, in an e-mail dated July 1, 2000, to Shapiro,

21   Vaughn, Six, Merk, and Nissenbaum, stated, "I softened the last reference to the liquidation of the

22   interest in the LLC so it sounds less like an event that we know will happen in the near future."

23   (GX 144 (emphases added).) However, LLC liquidation was part of the eighth of 13 specified steps

                                                        13
 1   that were necessary for the success of an Add-On transaction. (See GX 115 (Vaughn e-mail dated

 2   May 18, 2000, to Coplan and Shapiro).) As Six testified, "liquidation of the interest in the LLC" in

 3   fact "was one of the steps that was required to obtain the tax benefits." (Tr. 2410.)



 4          3. Shapiro and PICO

 5                  The PICO (or Personal Investment Corporation) tax shelter was a tax deferral and

 6   conversion strategy that involved investments in an S corporation, called PICO, by the taxpayer and

 7   another shareholder. The PICO would engage in straddle transactions that generated offsetting gains

 8   and losses, with only the losses allocated to the taxpayer. These capital losses could be used by the

 9   taxpayer to offset his capital gains from unrelated sources. (See Tr. 3736.)

10                  Cinquegrani, in early 2000, was an attorney who was approached, for an opinion letter,

11   by the person who had conceived of PICO and who instructed Cinquegrani to contact Richard

12   Shapiro, E&Y's lead contact for PICO. (See Tr. 3739-42.) In Cinquegrani's initial conversation with

13   Shapiro, there was no discussion of any business purpose or non-tax reason for PICO. (See id.

14   at 3743-44.)

15                  Cinquegrani proceeded to have legal issues researched, and he kept Shapiro informed

16   of the results. (See, e.g., Tr. 3748-49.) He had many conversations with Shapiro, "discuss[ing]

17   various provisions of the Internal Revenue Code that may apply to the transaction, and [Shapiro]

18   asked about what issues were or were not being included in the opinion" (id. at 3773); and

19   Cinquegrani sent memoranda and drafts to Shapiro, who forwarded them to Coplan and Nissenbaum

20   (see id. at 3751-54, 3769-70). Cinquegrani sent summaries of the conclusions to be included in the

21   requested opinion letter, and drafts of proposed fact sections--based on "assumed" facts, as there were

22   no PICO clients at the time (id. at 3752-53)--to support the already-reached legal conclusions (see id.

                                                       14
 1   at 3750-54; id. at 3761 ("by the time [Cinquegrani] drafted [this] facts section," the PICO opinion

 2   letter "was largely in its final form").)

 3                   After receiving Cinquegrani's draft of the fact section, Shapiro sent Cinquegrani an

 4   e-mail listing economic-substance representations that had been made in connection with a different

 5   transaction, stating that he was sending them for discussion purposes "as to tone, etc., not specifically

 6   for content." (GX 653 (Shapiro e-mail dated August 7, 2000 (bold in original)).) Shapiro's first four

 7   sample representations referred to "substantial non-tax" business purposes for the transaction; and the

 8   last stated that "[i]nvestor has reviewed the description of the transactions contained in the Letter and

 9   such description is accurate and complete, and there are no pertinent facts relating to the Transactions

10   that have not been set forth in such description"; but Shapiro's samples said nothing about the

11   transaction's tax ramifications. (Id.) Cinquegrani testified that he added some of Shapiro's sample

12   representations to the ensuing version of the PICO opinion (see Tr. 3777); the substance of two

13   Shapiro samples asserting non-tax business purposes appeared as client representations in

14   Cinquegrani's opinion letter (see, e.g., GX 663).

15                   Cinquegrani testified that he knew he was drafting a document that was misleading as

16   to the true purpose of the PICO transaction and that he was engaged in wrongdoing. (See Tr. 3761.)

17   For example, the fact description began by stating that the LLC "is offering qualified investors ('the

18   investors') the opportunity to create a special purpose investment management company to capitalize

19   on [the LLC's] expertise in the foreign exchange markets and general investment management

20   services"; Cinquegrani testified that that was not an accurate statement because "the real reason for

21   offering this vehicle, which is the PICO, is to provide tax losses for investors." (Id. at 3754-56.) The

22   description contained other false or misleading statements as well (see id. at 3756-61), because

23   although PICO was designed "[t]o make available to the investor significant losses" (id. at 3758),

                                                         15
 1   Cinquegrani's "intention was to describe the transaction as much as possible as an ordinary business

 2   deal and to downplay all the tax aspects" (id. at 3756), "deemphasizing wherever possible tax

 3   benefits" (id. at 3760). No one at E&Y expressed any concerns about the language of the letter. (See

 4   id. at 3761.)

 5                   In sum, Cinquegrani testified that there was a "cover story element to the beginning

 6   of the opinion that misleads about what the transaction is all about" (Tr. 4015) and that the opinion

 7   letter contained statements that were false and misleading (see id. at 3754-81), indeed, "wildly

 8   misleading" (id. at 3779). Cinquegrani was asked why he did not tell "Shapiro" and others that the

 9   opinion letter contained a false cover story. (Id. at 4021.) Cinquegrani testified that he "didn't feel

10   a need to say, oh, by the way, the stuff we are writing doesn't really reflect what's really going on,"

11   because "the key players, that you mentioned, Mr. Shapiro [and others], they all participated in

12   creating the story." (Tr. 4021-22.)



13           4. Nissenbaum

14                   Nissenbaum too was a core member of the SISG Group headed by Coplan. (See

15   Tr. 2135-37, 2236.) I disagree with the Majority's view that the evidence was insufficient to permit

16   a reasonable inference that Nissenbaum knew of and participated in the conspiracy to impede the IRS

17   in the performance of its lawful functions.

18                   As the above discussion of Shapiro reveals, Nissenbaum too received numerous

19   e-mails from Coplan, as well as several from Shapiro, urging concealment of facts that were material

20   to the tax-minimization or tax-elimination goals of the COBRA, CDS, Add-On, and PICO shelters.




                                                       16
 1   These included:

 2           - Coplan's July 17, 2001 e-mail, GX 555, ordering retention of documents "supporting
 3           the economic purpose and bona fide nature of the investment in the [COBRA]
 4           transaction" (emphasis added), along with legal opinions and documents relating to
 5           the currency trades, but ordering the immediate deletion and disposition of any other
 6           materials related to COBRA;

 7           - Coplan's July 23, 2001 e-mail, GX 602, about a "PICO Materials Leak," stressing
 8           that leaking "of the materials to . . . the government WOULD have calamitous results";

 9           - Shapiro's February 8, 2000 e-mail on CDS, GX 66, "seriously" "question[ing]"
10           whether the "[c]learly . . . necessary" "fact that our swap will be terminated early"
11           should be included in "a document";

12           - Shapiro's April 14, 2000 e-mail on CDS, GX 100, terming it "essential" that the
13           statements that "'Calculations assume utilization of the Early Termination Provision'"
14           "be deleted" from the model documents;

15           - Coplan's July 1, 2000 e-mail, GX 144, stating--despite the fact that liquidation of the
16           interest in the LLC was in fact a step that was required in order to achieve the planned
17           tax benefits--that Coplan had "softened the" Add-On announcement letters' "reference
18           to the liquidation of the interest in the LLC so it sounds less like an event that we
19           know will happen in the near future."

20                   I see nothing that required the jury to regard Nissenbaum as a disinterested recipient

21   of random e-mails. These were communications sent to him as a core member of the SISG group,

22   which prepared presentations, prepared templates for letters to and for clients, and prepared templates

23   for responses to IRS inquiries. Plainly Nissenbaum did review e-mails sent to him with regard to

24   letters to be sent to the IRS in seeking amnesty. With regard to PICO, Dougherty testified that he

25   prepared a disclosure letter using an "amnesty template . . . coming from Mr. Nissenbaum" (Tr. 1761;

26   see id. at 1317-18); and that template did not "disclos[e] all the [taxpayer's] motives" for entering into

27   the transaction (id. at 1762) and did not "mention the primary motivation of deferring and reducing

28   taxes" (id. at 1761). Nissenbaum approved the letter (prepared from his template) without substantive

29   change as "Good to go" (GX 583 (Nissenbaum e-mail dated April 18, 2002); see also Tr. 1641). With


                                                        17
 1   regard to Add-On, Coplan solicited--and received--comments from Nissenbaum on the proposed

 2   amnesty template (which adopted misstatements in the opinion letters received by E&Y clients, the

 3   opinion letters, in turn, having been prepared from the form representation letters for the clients (see,

 4   e.g., GX 786 (e-mail dated March 30, 2001, from Brent Clifton, attorney who wrote Add-On opinion

 5   letters, to Shapiro, Coplan, and Nissenbaum); Tr. 2486-88)). The amnesty letter templates did not

 6   disclose the taxpayer's actual motive, i.e., tax-elimination. Nissenbaum's only suggestion was to

 7   eliminate some investment details; otherwise, he said, "[t]he disclosure looks fine to me" (GX 491

 8   (Nissenbaum e-mail dated March 5, 2002, to Coplan and Shapiro); see Tr. 4663).

 9                   Nor can it reasonably be argued that Nissenbaum did not realize the import of any of

10   these nondisclosures. In March 2000, when he became aware that a regional E&Y tax department

11   employee had sent to some 18 other tax department employees a Power Point presentation describing

12   an SISG tax shelter, Nissenbaum instructed the director of that region to "make it clear" that "nothing

13   from SISG is to be circulated this widely" (GX 94 (Nissenbaum e-mail dated March 22, 2000

14   (emphasis in original))). Nissenbaum stated, "This could shut this down sooner than sending the

15   PowerPoint to the IRS!" (Id.)



16   B. The Convictions of Shapiro and Nissenbaum on Counts Two and Three

17                   Counts Two and Three of the superseding indictment charged Shapiro and Nissenbaum

18   with substantive offenses, to wit, attempted tax evasion in violation of 26 U.S.C. § 7201 in connection

19   with the Add-On tax shelter. Section 7201 prohibits "any conduct, the likely effect of which would

20   be to mislead or to conceal," Spies v. United States, 317 U.S. 492, 499 (1943). The jury was

21   instructed, inter alia, that it could find defendants guilty of these substantive offenses on the basis of

22   the principle established in Pinkerton v. United States, 328 U.S. 640 (1946), that when the evidence

                                                        18
 1   establishes that a conspiracy existed, a member of the conspiracy may be held liable for all acts of

 2   wrongdoing performed by other coconspirators during the course of and in furtherance of the

 3   conspiracy, see id. at 646-47.

 4                  Coplan and Vaughn were convicted of the conspiracy alleged in Count One and of the

 5   substantive tax evasion offenses alleged in Counts Two and Three. Given the evidence that supports

 6   the convictions of Shapiro and Nissenbaum of the Count One conspiracy, discussed in Part A above,

7    the jury could easily find that the tax evasions by Coplan and Vaughn were in furtherance of the

8    conspiracy and were foreseeable to Shapiro and Nissenbaum. I would thus uphold the verdicts against

 9   Shapiro and Nissenbaum on Counts Two and Three on the Pinkerton theory.

10                  The Majority rejects the applicability of the Pinkerton theory "[f]or substantially the

11   reasons that" the Majority would reverse the convictions of Shapiro and Nissenbaum for conspiracy,

12   Majority Opinion ante at 32-34. That is, the Majority views the evidence as insufficient to permit the

13   inference that Shapiro and Nissenbaum knew of and participated in the Count One conspiracy, i.e.,

14   that they were in fact members of the conspiracy.

15                  In my view, the evidence discussed in Part A above was ample to permit the jury to

16   infer that Shapiro and Nissenbaum knew of and participated in the proven conspiracy. Each was a

17   core member of SISG, the tax-shelter-marketing arm of E&Y; they received numerous e-mails,

18   principally from Coplan, cautioning against allowing E&Y materials marketing those shelters to fall

19   into the hands of "the IRS." And similar warnings were explicitly issued by Shapiro and Nissenbaum

20   themselves. The numerous warnings and stated goal to maintain sanitized files need not themselves

21   have been unlawful in order to show, as they did, that Shapiro and Nissenbaum were fully aware of

22   the efforts to conceal the tax purposes of these shelters from the IRS. And the evidence was sufficient

23   to permit the jury to infer that Shapiro and Nissenbaum engaged in misleading conduct that was

                                                       19
1   plainly unlawful. Shapiro, for example, not only discussed with Dougherty false statements that they

2   could proffer to the IRS in connection with the audit of the WRB Lake partners but also attended the

3   IRS interview at which Dougherty told such "lie[s]." And both Shapiro and Nissenbaum reviewed

4   and approved form letters to be submitted by E&Y clients to the IRS, in support of amnesty, that

5   proffered business purposes, did not disclose the tax-reduction or tax-elimination motivation, and

6   stated that no pertinent facts were undisclosed. In sum, I conclude that the evidence was sufficient

7   to support the convictions of Shapiro and Nissenbaum of conspiracy as charged in Count One and of

8   the substantive offenses charged in Counts Two and Three.




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