                                                                  FILED
                                                       United States Court of Appeals
                                                               Tenth Circuit

                                                           November 23, 2015
                                  PUBLISH                 Elisabeth A. Shumaker
                                                              Clerk of Court
                   UNITED STATES COURT OF APPEALS

                                TENTH CIRCUIT


 UNITED STATES OF AMERICA,

       Plaintiff - Appellee,

 v.
                                                    No. 14-5147
 IQBAL MAKKAR, a/k/a Jack Singh,
 a/k/a Iqbal Singh Makkar,

       Defendant - Appellant.

 UNITED STATES OF AMERICA,

       Plaintiff - Appellee,
                                                    No. 14-5148
 v.

 GAURAV SEHGAL, a/k/a Ricky
 Sehgal,

       Defendant - Appellant.


               Appeals from the United States District Court
                    for the Northern District of Oklahoma
        (D.C. Nos. 4:13-CR-00205-CVE-1 and 4:13-CR-00205-CVE-2)


Guy A. Fortney (Robert R. Nigh, Jr. and Corbin C. Brewster on the briefs),
Brewster & De Angelis, Tulsa, Oklahoma, for Defendant-Appellant Iqbal Makkar.

Stanley D. Monroe (Kirsten L. Palfreyman with him on the briefs), Monroe &
Keele, P.C., Tulsa, Oklahoma, for Defendant-Appellant Gaurav Sehgal.
Leena Alam, Assistant United States Attorney (Danny C. Williams, Sr., United
States Attorney, with her on the briefs), Tulsa, Oklahoma, for Plaintiff-Appellee.



Before TYMKOVICH, Chief Judge, GORSUCH and McHUGH, Circuit Judges.


GORSUCH, Circuit Judge.


      Iqbal Makkar and Gaurav Sehgal ran the “Gitter Done,” a small town

convenience store in northeastern Oklahoma. When questions surfaced about the

incense they carried on their shelves, the men spoke with state law enforcement

officers, offered to have the officers test the incense to determine its legality, and

offered as well to stop selling the product until the results came in. But this

cooperation with state authorities apparently won the men little admiration from

federal investigators: soon enough they found themselves under indictment and

convicted for violating the Controlled Substance Analogue Enforcement Act

(Analogue Act), conspiracy, and money laundering. In this appeal Mr. Makkar

and Mr. Sehgal contend that the government overreached at trial — in the jury

instructions it sought and won, and again in its successful efforts to exclude

evidence of their cooperation with law enforcement. After our own review of the

record, we have to agree.

                                          *




                                         -2-
      Take first Mr. Makkar’s argument about the jury instructions. The

Analogue Act is a curious animal. It’s familiar learning that the Controlled

Substances Act (CSA) proscribes the knowing possession and distribution of

certain listed substances (marijuana, cocaine, heroin, and the like). What’s less

well known is that the Analogue Act picks up where the CSA leaves off,

forbidding the possession and distribution of substances analogous to those listed

in the CSA. In this way, the relationship between the two statutes is not unlike

the relationship between the different sections of the Armed Career Criminal Act

(ACCA). Much as here, one part of that statute lists certain specific violent

felonies and imposes special punishments for their commission. Meanwhile,

another part of that statute — what’s called its residual clause — extends the

statute’s punishments to other, unspecified offenses that can claim similarity to

listed ones.

      The resemblance between the Analogue Act and the residual clause of the

ACCA might raise some questions in your mind. After all, the Supreme Court in

Johnson v. United States, 135 S. Ct. 2551 (2015), recently declared the ACCA’s

residual clause too vague to permit its constitutional application. But so far at

least the Court hasn’t reached a similar judgment about the Analogue Act. In

fact, the Court only recently gave the Analogue Act a narrow construction that

may go some way to alleviating potential concerns about the vagueness of its

terms. In McFadden v. United States, 135 S. Ct. 2298 (2015), the Court accepted

                                         -3-
the government’s concession that to establish a violation of the Analogue Act it

must prove the drug in question bears two features: (1) it must be substantially

similar in chemical structure to a schedule I or II CSA controlled substance, and

(2) it must have, or be represented or intended to have, an effect on the central

nervous system that is substantially similar to that of a schedule I or II CSA

controlled substance. Id. at 2305 n.2. When it comes to mens rea, the Court

further explained, the government must show that the defendant knew the drug he

possessed either (1) had both of these features, or (2) was controlled by the CSA

or Analogue Act. Id. at 2305. The Court seemed to suggest that this narrow

construction would help alleviate potential vagueness concerns, at least in the

face of a facial challenge. Id. at 2307. But whether this construction will suffice

to save the Analogue Act from the same fate as the ACCA’s residual clause may

still remain to be seen. It’s an open question, after all, what exactly it means for

chemicals to have a “substantially similar” chemical structure — or effect. And

whether terms like those will admit of fair application and afford citizens fair

notice, or whether we will find ourselves wading incrementally, in one as-applied

challenge after another, deeper into an analytical swamp much as we did with the

ACCA’s residual clause litigation.

      Still, in this case we face a much more prosaic problem. The government

sought and secured an ambitious mens rea instruction that just will not square

with the text of the statute or McFadden. At trial, the government didn’t attempt

                                         -4-
to show that Mr. Makkar or Mr. Sehgal knew the incense they sold was unlawful

under the CSA or Analogue Act — the second method of proving mens rea

McFadden prescribed. Instead, the government attempted to show mens rea only

in the first manner McFadden discussed — by showing that the defendants knew

that the incense they sold had (1) a substantially similar chemical structure to

JWH-18 (a synthetic cannabinoid with marijuana-like effects listed as a CSA

controlled substance) and (2) a substantially similar effect to that of marijuana

(another CSA listed substance). So far, at least for current purposes we may

assume, so good. 1 The difficulty is that, after choosing to proceed this way, the

government sought to shrug off the first of the mens rea requirements it had just

agreed to shoulder. In fact, as far as we can tell, at trial the government

introduced no evidence suggesting that the defendants knew anything about the

chemical structure of the incense they sold. And as a way around this

shortcoming the government sought — and the district court agreed to issue — an

instruction permitting the jury to infer that the defendants knew the incense they

sold had a substantially similar chemical structure to JWH-18 from the fact they

knew the incense had a substantially similar effect to marijuana. Coming at the

point another way, the government asked for and won the right to collapse its two

      1
         One wrinkle: note that the government sought to prove the incense bore
a similar structure to one CSA listed drug and a similar effect to another.
Whether this is permissible under the Analogue Act, or whether it might
contribute to questions about the constitutionality of its application, are not issues
presented to us in this appeal and we do not pass upon them one way or the other.

                                         -5-
separate elemental mens rea burdens into one. Under the inferential instruction it

secured, the government was able to argue to the jury that it should find the first

mens rea element satisfied beyond a reasonable doubt merely (and without more)

because it found the second satisfied beyond a reasonable doubt.

      This surely made trial easier for the government, but just as surely it means

we must undo the judgment now. Before a district court may issue an instruction

permitting the jury to infer the presence of even a single essential element from a

set of facts the inference must — at the least — be shown capable of leading a

rational trier of fact to the conclusion that the element in question is proven to the

level demanded by the applicable standard of proof. United States v. Berry, 717

F.3d 823, 829 (10th Cir. 2013). Neither may a district court ever issue

instructions that effectively relieve the government of proving each essential

element specified by Congress. See United States v. Gaudin, 515 U.S. 506, 511

(1995). Both of these principles were violated here. The government’s

instructional inference invited the jury to infer the presence of one essential

element from another, effectively collapsing two independent statutory inquiries

into one. And it did so only by resort to a logical fallacy, a hasty generalization

or associational error — an unwarranted assumption that because certain things

share one characteristic they must share others. As a matter of common

experience and logic, the fact that one drug produces a similar effect to a second

drug just doesn’t give rise to a rational inference — let alone rationally suggest


                                         -6-
beyond a reasonable doubt — that the first drug shares a similar chemical

structure with the second drug. And it most certainly does not give rise to a

qualifying inference that the first drug shares a similar chemical structure with a

third drug — as the government was, in fact, allowed to argue to the jury in this

case.

        The government now admits all this, expressly acknowledging on appeal

that different drugs can bear similar effects while lacking similar chemical

structures. As Mr. Makkar notes by way of example, Tylenol and Aspirin may do

much the same job on your aches and pains but most scientists do not place them

in the same chemical group. See Harold E. Doweiko, Concepts of Chemical

Dependency 208-09 (9th ed. 2015). Cocaine and methamphetamine are also

sometimes said to have similar effects, but their chemical structures are rarely

said to be substantially similar even by the government. See Drug Enforcement

Administration, Drugs of Abuse 51 (2015); 2 Encyclopedia of Applied

Developmental Science 1062 (Celia B. Fisher & Richard M. Lerner eds., 2005).

Even closer to home, the DEA has issued published guidance acknowledging that,

while JWH-18 and marijuana have similar effects, the former “is not related in

chemical structure to [THC] or other cannabinoids contained in the cannabis

plant.” Drug Enforcement Administration, JWH-018 1-Pentyl-3-

(1-naphthoyl)indole (2013). And closer to home still, the government’s own

chemistry experts advised the government and court in another case decided


                                         -7-
before Mr. Makkar’s trial that the very inferential instruction it sought here “is

not scientifically sound.” United States v. Lane, No. CR-12-01419-PHX-DGC,

2013 WL 3716601, at *1 (D. Ariz. July 13, 2013).

      But while conceding now that the jury instruction it sought and won in this

case was wrong, the government also insists that the error isn’t consequential

enough to worry over. The government points to the fact that Mr. Makkar didn’t

object to the instruction at trial. And the government reminds us that, in these

circumstances, we apply the plain error standard of review. Under that standard,

before reversing we must be persuaded that (1) the district court erred; (2) the

error was plain; (3) the error affected a defendant’s substantial rights; and (4) the

error seriously affected the fairness, integrity, or public reputation of a judicial

proceeding. United States v. Olano, 507 U.S. 725, 732 (1993). The government

accepts that the first element — error — is present in this case, but pitches an

avid battle on the second, insisting that the instructional error here can’t fairly be

described as plain. By way of support it points us to United States v. Turcotte,

405 F.3d 515 (7th Cir. 2005) — a decision that arguably once endorsed the

government’s inferential instruction. From the fact that another court once

committed the same error it did in this case, the government asks us to reason, the

error it invited doesn’t qualify as a plain one.

      This argument depends on a hasty generalization of its own. The fact other

circuits have committed an error can supply “strong evidence” that it doesn’t


                                          -8-
qualify as a “plain” one. United States v. Story, 635 F.3d 1241, 1248 (10th Cir.

2011). But another circuit’s commission of an error doesn’t necessarily and

always “control” the plain error inquiry. United States v. Ahidley, 486 F.3d 1184,

1193 n.7 (10th Cir. 2007); see also United States v. Overholt, 307 F.3d 1231,

1256 (10th Cir. 2002). The fact that able judges elsewhere once committed an

error may go some way toward showing it isn’t plain, but it doesn’t always and

necessarily prove the point as the government seems to suppose. Neither could it

sensibly do so. After all, to err is human — and to plainly err is too. Despite our

aspirations (and maybe sometimes our pretenses) we judges can hardly claim to

escape that fact of life. Certainly far greater minds than ours haven’t managed to

evade its grasp. See, e.g., Atom Energy Hope Is Spiked by Einstein, Pittsburgh

Post-Gazette, Dec. 29, 1934, at 13 (“The idea that man might some day utilize the

atom’s energy brought the only emphatic denial from [Einstein].”); Lord May,

Royal Society Anniversary Address, Dec. 2003, quoting Lord Kelvin (1895),

(“Heavier than air flying machines are not possible.”).

      When it comes to the particular error before us, too, we harbor no doubt

that it was plain by the time of the trial in this case. Yes, Turcotte appears to

have fallen into the same trap as the government did here. But even in the

government’s telling, no other circuit court repeated Turcotte’s mistake in all the

years between that decision in 2005 and the trial in this case in 2014. And surely

those years of precedential silence chirping around Turcotte — the fact that over


                                         -9-
the span of nearly a decade no other circuit apparently endorsed its reasoning —

must be heard and accounted for. Even more dramatically, we know that in those

intervening years the government in Lane expressly disavowed Turcotte’s

inference as scientifically unsound. And we know the DEA effectively rejected

the inference as irrational too when it acknowledged that JWH-18 and marijuana

bear similar effects but do not share a similar chemical structure. These

developments, moreover, only confirmed what’s been true all along — that the

government’s inference depends on what can only be described as an assumption

inconsistent with logic and experience — an assumption that just because one

drug shares a particular trait in common with a second drug the first also shares a

different trait in common with the second drug — or even a third drug. And

while we cannot ignore the holding of another circuit when assessing the

plainness of an error, we equally cannot ignore so many countervailing

considerations like these. In this case, those countervailing considerations seem

to us to speak clearly and loudly to the plainness of the government’s error and in

a way even Turcotte cannot fairly obscure. Indeed, we find it hard to see how we

might fairly describe an error as anything less than plain when the government

itself concedes the error on appeal and did so (effectively twice) even before the

trial in this case.

       Of course, that still leaves the remaining two elements of the plain error

test. But our discussion on these points can be brief. The government doesn’t


                                        - 10 -
dispute either element and it’s easy to see why. At trial, the government sought

to prove mens rea by way of the first route McFadden approved. Yet, it made no

effort to carry the burden of producing evidence suggesting that the defendants

knew the chemical composition of the incense they sold, relying instead entirely

and admittedly on an unsound inference. And surely a defendant’s substantial

rights and the integrity of judicial proceedings are both implicated when he is

relegated to federal prison even though the government concedes it hasn’t proven

what the law demands it must prove to send him there. United States v.

Sabillon-Umana, 772 F.3d 1328, 1333-34 (10th Cir. 2014). 2

                                          *

      With the plain error test satisfied, it might seem we’ve reached the end of

the road on Mr. Makkar’s challenge to the jury instructions. But at oral argument

on appeal the government sought to introduce a new argument in defense of the

instructions it sought and won. To bear its burden of showing mens rea under

McFadden, the government contended, it must prove only that the defendant knew

the drug in question has a substantially similar effect to a class I or II CSA




      2
         In this light, you might also wonder if double jeopardy precludes a retrial
in this case. Given the parties’ intent focus on the instructional error in this
appeal, however, that’s a matter we decline to pass upon one way or the other at
this time and leave for the district court to address in the first instance on remand
in the event the government should seek a retrial.


                                        - 11 -
controlled substance. And, the government contended, it proved at least that

much at trial.

      This new argument concerns us on various fronts. Not only does it appear

too late in these proceedings to be taken seriously — presented for the first time

at argument. And not only is it inconsistent with the jury instructions the

government itself sought and the trial court issued in this case. It also disregards

the Supreme Court’s recent teachings and the statutory text. After all and as

we’ve seen, McFadden imposes a far more challenging mens rea requirement than

the government is willing now to admit. McFadden requires the government to

show that the defendant: (1) knew the drug in question had both a similar

chemical structure and similar effects to a controlled substance, or (2) knew the

drug in question was unlawful under the Analogue Act or CSA. 135 S. Ct. at

2305. Proof that the defendant merely knew the drug he sold had a similar effect

to a controlled substance is never enough. And the plain language of the statute

underscores and confirms what McFadden clearly explained. As written, the

Analogue Act makes it a crime to possess or distribute a drug that both (1) is

substantially similar in chemical structure to a schedule I or II CSA controlled

substance, and (2) has, or is represented or intended to have, an effect on the

central nervous system that is substantially similar to that of a schedule I or II

CSA controlled substance. Both elements are essential to a conviction and the

government offers no sensible way or reason why a mens rea requirement applied


                                        - 12 -
to the statute might take an olympian leap over the first essential element and

touch down only on the second. Neither can we discern for ourselves any

plausible argument along these lines. Cf. Flores-Figueroa v. United States, 556

U.S. 646, 650 (2009) (noting that when a statute introduces elements of a crime

with the word “knowingly,” that means it applies to “all the subsequently listed

elements”).

                                           *

      Where Mr. Makkar identifies an instructional error, Mr. Sehgal focuses our

attention on an evidentiary error. As part of their defense at trial Mr. Makkar and

Mr. Sehgal sought to introduce evidence showing that they asked state law

enforcement agents to test the incense to assure its legality under state law — and

that they offered to stop selling the incense until the results came in. In the

defendants’ view, this evidence was relevant to the questions whether they knew

the chemical structure of the incense and whether they knew its structure was

substantially similar to the structure of controlled substances. After all, they

sought to argue, why run a test if you already know the answer? Let alone agree

to have law enforcement administer the test if you know the answer will be

unfavorable to you under either state or federal law? Especially when state and

federal agents often cooperate with one another (as, in fact, they did in this case)?

In reply to the defendants’ trial plans, the government filed a written motion in

limine seeking to exclude the evidence as irrelevant under Rule 401 of the Federal


                                         - 13 -
Rules of Evidence. And here again the district court adopted the government’s

position. In doing so it rejected the defendants’ suggestion that the evidence was

relevant because “[i]f they knowingly sold [the incense], and it is an analogue,

it’s illegal. [They] don’t have to know the chemical composition.” Aplt. App.

Vol. II, at 321.

      While we normally afford a district court a good deal of discretion on

evidentiary rulings, we do not defer to rulings that rest on legal error. United

States v. Toombs, 713 F.3d 1273, 1278 (10th Cir. 2013). And the government’s

motion in limine, adopted by the district court, clearly depends on a mistaken

view of the Analogue Act. As we’ve seen, McFadden’s first path for proving

mens rea — the path the government chose to pursue at trial in this case —

required it to prove a good deal more than that the defendants knowingly sold the

incense. The government had to prove that the defendants knew the incense had

both similar effects and a similar chemical structure to a controlled substance.

Neither does anyone before us even attempt to suggest that the defendants’

proffered evidence was irrelevant to these properly controlling questions. The

government did not attempt to suggest so much at trial, the district court did not

contend so much in its ruling, and the government does not make any effort in

this direction on appeal.

      Instead and again the government replies that, even if it invited error at

trial, the error it invited was (again) immaterial. In doing so, the government this


                                       - 14 -
time points to harmless error doctrine and reminds us that, even when a defendant

rightly identifies and objects to an error at trial, federal appellate courts aren’t in

the business of supplying remedies where they aren’t needed — where the error in

question did not affect the defendant’s substantial rights. See Fed. R. Crim. P.

52; 28 U.S.C. § 2111.

      All that’s true enough but we don’t see how it might fairly describe the

error here. It’s the government’s burden of showing any error it invited is only

harmless. And toward that end in this case the government stresses that Mr.

Makkar and Mr. Sehgal were allowed to introduce other evidence about their

mens rea. From this fact, the government would have us conclude that the

erroneously excluded evidence was merely cumulative. But this represents

another leap of logic longer than we can safely take. As a matter of common

sense and our collective experience, we have a hard time imagining more

powerful proof that a defendant didn’t know the chemical composition of a drug,

and didn’t know it was substantially similar to an unlawful substance, than

evidence that he turned to law enforcement for information about the drug’s

composition and offered to suspend sales until tests could be performed. Indeed,

it’s difficult for us to imagine why the government would have opposed the

introduction of this evidence and taken the trouble to present a written motion on

that score but for its extraordinary power to persuade the jury on questions like

these. See United States v. Yarbrough, 527 F.3d 1092, 1103 (10th Cir. 2008)


                                          - 15 -
(When an error deprives a defendant of “important evidence relevant to a sharply

controverted question going to the heart of [the] defense, . . . substantial rights

[are] affected.”).

                                           *

      Mr. Makkar and Mr. Sehgal present several other arguments for reversal —

at least some of which raise some potentially troubling questions in their own

right. For example, they complain that the government endorsed and the district

court admitted unreliable and inflammatory testimony about the health effects of

the incense. They point by way of illustration to one government witness who

testified before the jury that the incense killed his friend — even though the

friend was alive and apparently well — and scheduled to testify later the same

day. They point as well to the calculation of their advisory guidelines sentences.

In most cases, they note, inert materials associated with illicit drugs are added

into guidelines calculations at the “drug quantity table” stage, with the aim of

capturing the actual “street weight” of the drugs as sold. See U.S.S.G. § 2D1.1.

But in this case, they tell us, the district court included inert materials at an

earlier stage, when it applied the “drug equivalency table.” And this choice

meant the inert materials exerted something like a geometric effect on their

advisory guidelines sentencing calculations. Thus calculated, they say, the

guidelines attributed to them not the actual “street weight” of the inert materials

they sold but 167 times that weight. See id. The men argue that in following this


                                         - 16 -
path the district court misread the guidelines, which most expressly reference

inert materials in a note to the drug quantity table, not the drug equivalency table.

And they argue their resulting sentences were irrationally inconsistent with the

sentencing commission’s goal of seeking sentences that account for the actual

street weight of illicit drugs as sold. We see no need, however, to resolve the

defendants’ additional objections along these and other lines. Whether or not

their arguments bear merit, we think the essential point by now amply evident:

their convictions rest on legal errors that cannot be easily dismissed as harmless.

Neither do we assume the additional putative errors they complain of will

necessarily recur: to the contrary and as we’ve seen, it’s unclear at this point

whether the men can be lawfully retried consistent with the law’s demands.

      Mr. Makkar’s and Mr. Sehgal’s convictions for violating the Analogue Act

are vacated. Because the putative violation of the Analogue Act was the only

predicate crime to support their convictions for conspiracy and money laundering,

Mr. Makkar’s and Mr. Sehgal’s convictions on these counts are vacated as well.

The case is remanded and any further proceedings shall conform with this

opinion.




                                        - 17 -
