     12-2509-cv
     Roth v. The Goldman Sachs Group, Inc., et al.

 1                        UNITED STATES COURT OF APPEALS

 2                            FOR THE SECOND CIRCUIT

 3                               August Term, 2012

 4

 5   (Argued: May 8, 2013                            Decided: January 29, 2014)

 6                             Docket No. 12-2509-cv

 7         - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -

 8   ANDREW E. ROTH, DERIVATIVELY ON BEHALF OF LEAP WIRELESS
 9   INTERNATIONAL, INC.,
10
11               Plaintiff-Appellant,
12
13                  v.
14
15   THE GOLDMAN SACHS GROUP, INC., GOLDMAN, SACHS & CO., LEAP
16   WIRELESS INTERNATIONAL, INC.,
17
18               Defendants-Appellees.
19
20
21   - - - - - - - - - - - - - - - -- - - - - - - - - - - - - - - - -
22
23   B e f o r e:      WINTER, CABRANES, and LIVINGSTON, Circuit Judges.
24
25         Appeal from a judgment of the United States District Court

26   for the Southern District of New York (J. Paul Oetken, Judge),

27   dismissing appellant’s derivative action for failure to state a

28   claim.   Appellant sought to hold appellees liable for failing to

29   disgorge “short-swing profits” as required by Section 16(b) of

30   the Securities Exchange Act and Securities and Exchange

31   Commission Rule 16b-6(d).       Appellees were statutory insiders when

32   they wrote call options but not when the same options expired

33   less than six months later.       We affirm.

                                           1
 1                                  GLENN OSTRAGER (Paul D. Wexler,
 2                                  Kornstein Veisz Wexler & Pollard LLP, on
 3                                  the brief), Ostrager Chong Flaherty &
 4                                  Broitman P.C., New York, NY, for
 5                                  Plaintiff-Appellant.
 6
 7                                  LAWRENCE T. GRESSER (Daniel H. Tabak &
 8                                  Alexis G. Stone, on the brief), Cohen &
 9                                  Gresser LLP, New York, NY, for
10                                  Defendants-Appellees.
11
12                                  Geoffrey F. Aronow, Michael A. Conley,
13                                  Jacob H. Stillman, John W. Avery,
14                                  Benjamin M. Vetter, Securities and
15                                  Exchange Commission, Washington, D.C.,
16                                  for Amicus Curiae Securities and
17                                  Exchange Commission.
18
19
20   WINTER, Circuit Judge:
21
22        Andrew Roth appeals from Judge Oetken’s dismissal under Fed.

23   R. Civ. P. 12(b)(6) of his derivative action on behalf of Leap

24   Wireless International, Inc. (“Leap”).           He seeks to hold the

25   Goldman Sachs Group and its wholly owned subsidiary Goldman,

26   Sachs & Co. (collectively, “Goldman”) liable under Section 16(b)

27   of the Securities Exchange Act (“Exchange Act”)1 and Rule

          1
              Section 16(b) provides:
                  (b) Profits from purchase and sale of security within six months

                  For the purpose of preventing the unfair use of information which
                  may have been obtained by such beneficial owner, director, or
                  officer by reason of his relationship to the issuer, any profit
                  realized by him from any purchase and sale, or any sale and
                  purchase, of any equity security of such issuer (other than an
                  exempted security) or a security-based swap agreement involving
                  any such equity security within any period of less than six
                  months, unless such security or security-based swap agreement was
                  acquired in good faith in connection with a debt previously
                  contracted, shall inure to and be recoverable by the issuer,
                  irrespective of any intention on the part of such beneficial
                  owner, director, or officer in entering into such transaction of
                  holding the security or security-based swap agreement purchased or
                  of not repurchasing the security or security-based swap agreement
                  sold for a period exceeding six months. Suit to recover such
                  profit may be instituted at law or in equity in any court of
                  competent jurisdiction by the issuer, or by the owner of any
                  security of the issuer in the name and in behalf of the issuer if
                  the issuer shall fail or refuse to bring such suit within sixty
                  days after request or shall fail diligently to prosecute the same
                  thereafter; but no such suit shall be brought more than two years
 1   16b-6(d)2 for their failure to disgorge “short-swing profits”

 2   derived from writing call options on Leap stock.

 3        Although Section 16(b) is long in the tooth –- older even

 4   than the author of this opinion –- and the subject of countless

 5   judicial interpretations, it seems to be an ever-growing fount of

 6   close questions as to its meaning.        The issue here arises from

 7   the fact that Goldman owned over ten percent of Leap’s equity

 8   shares –- a statutory insider under Section 16(b) -- when it

 9   wrote certain call options, but owned under ten percent when the

10   unexercised options expired less than six months later.            The

11   principal issues are whether:       (i) a call option’s expiration

12   within six months of its writing constitutes a “purchase” for

13   Section 16(b) purposes that can be matched to the “sale” that is

14   deemed under Rule 16b-6(a) to occur at the option’s writing; and

15   (ii) if so, whether the loss of statutory insider status before

16   the expiration eliminates the need for disgorgement under Section

17   16(b).   Concluding the expiration was a “purchase” but that the



                after the date such profit was realized. This subsection shall
                not be construed to cover any transaction where such beneficial
                owner was not such both at the time of the purchase and sale, or
                the sale and purchase, of the security or security-based swap
                agreement or a security-based swap involved, or any transaction or
                transactions which the Commission by rules and regulations may
                exempt as not comprehended within the purpose of this subsection.
          15 U.S.C. § 78p(b).

          2
            Rule 16b-6(d) provides:
                (d) Upon cancellation or expiration of an option within six months
                of the writing of the option, any profit derived from writing the
                option shall be recoverable under section 16(b) of the Act. The
                profit shall not exceed the premium received for writing the
                option. The disposition or closing of a long derivative security
                position, as a result of cancellation or expiration, shall be
                exempt from section 16(b) of the Act where no value is received
                from the cancellation or expiration.
          17 C.F.R. § 240.16b-6(d).

                                          3
 1   Goldman defendants were not statutory insiders at the time of the

 2   “purchase,” the district court held that Goldman was not required

 3   to disgorge any profits.      We affirm.

 4                                   BACKGROUND

 5        Appellant’s complaint alleges the following.           Goldman owned

 6   common stock in Leap.      On September 30, 2009, Goldman’s ownership

 7   stake in the company surpassed ten percent, rendering it a

 8   statutory insider subject to the reporting and disgorgement

 9   requirements of Section 16.3       On the same date, Goldman wrote

10   32,000 call options that covered 3.2 million shares of Leap and

11   were exercisable at $39/share.       The options were sold at

12   $0.33/share for a total of $1,056,000 and bore an expiration date

13   of January 16, 2010.      On October 2, 2009, Goldman’s disposal of

14   Leap shares dropped its ownership stake below ten percent.

15        In an October 6, 2009, e-mail message to Leap, Goldman

16   disclosed that it had generated profits from purchases and sales

17   of Leap securities unrelated to the options described above

18   during the period when Goldman was a statutory insider.            Pursuant

19   to Section 16(b), Goldman (voluntarily) disgorged to Leap the




          3
             Section 16 applies to “[e]very person who is directly or indirectly
     the beneficial owner of more than 10 percent of any class of any equity
     security” of the issuer. 15 U.S.C. § 78p(a). Under Rule 16a-1(a), the
     definition of beneficial owner is found in Section 13(d) of the Exchange Act
     and accompanying rules. Under Section 13(d)(3), see id. § 78m(d)(3), “[w]hen
     two or more persons act as a . . . group for the purpose of acquiring,
     holding, or disposing of securities of an issuer, such syndicate or group
     shall be deemed a ‘person’ for the purposes of this subsection.” Appellant’s
     complaint alleges that the Goldman appellees-defendants constitute such a
     “group.” Because we are reviewing a dismissal under Fed. R. Civ. P. 12(b)(6),
     we must, therefore, assume that Goldman is a group subject to the statute’s
     requirements.

                                           4
 1   profits -- totaling about $203,000 -- derived from these

 2   transactions.

 3        On January 16, 2010, the call options at issue here expired

 4   unexercised.

 5        On June 14, 2011, appellant, a Leap shareholder, made a

 6   demand on Leap to sue Goldman under Section 16(b) and Rule

 7   16b-6(d) for Goldman’s alleged failure to disgorge profits earned

 8   by writing the short call options that expired unexercised within

 9   six months.     In response, Leap referenced the profits already

10   voluntarily disgorged by Goldman and communicated that it

11   “consider[ed] the matter closed.”

12        Appellant filed the present action on July 13, 2011.

13   Goldman and Leap (the latter as a nominal defendant) moved to

14   dismiss the action for failure to state a claim.    The district

15   court granted the motions, holding:    (i) Both a purchase and a

16   sale must exist to trigger liability under the statute.    Under

17   Section 16(b), the expiration of a short call option constitutes

18   a purchase to be matched with the sale that is deemed to occur
19   when the option is written.    (ii) Goldman was a statutory insider

20   only when the options were written, not when they expired.    (iii)

21   Goldman was, therefore, not required to disgorge profits earned

22   from writing the options because the statute requires statutory

23   insider status at the time of both purchase and sale.    Reliance
24   Elec. Co. v. Emerson Elec. Co., 404 U.S. 418, 423-25 (1972).

25   Appellant timely appealed.


                                        5
 1         After the close of briefing but before oral argument, we

 2   invited the SEC to submit an amicus curiae brief regarding the

 3   merits of the appeal.   That brief, when filed, agreed with the

 4   district court.

 5                               DISCUSSION

 6         “We review a district court’s dismissal of a complaint

 7   pursuant to Rule 12(b)(6) de novo.”   Operating Local 649 Annuity

 8   Trust Fund v. Smith Barney Fund Mgmt. LLC, 595 F.3d 86, 91 (2d

 9   Cir. 2010).

10         The question before us is whether, to fall under the

11   disgorgement requirements of Section 16(b) and Rule 16b-6(d), an

12   expiration of a call option is a “purchase” and the writer of a

13   call option must be a ten percent owner both at the time it

14   writes the option and at the time the option expires.    We begin

15   with the pertinent statutory and regulatory framework.
16   a)   Section 16(b)
17         Stated simply, liability under Section 16(b), quoted in Note

18   1, supra, attaches when “there was (1) a purchase and (2) a sale

19   of securities (3) by . . . a shareholder who owns more than 10
20   percent of any one class of the issuer's securities (4) within a
21   six-month period.”   Gwozdzinsky v. Zell/Chilmark Fund, L.P., 156
22   F.3d 305, 308 (2d Cir. 1998).   It is intended to “prevent[] the

23   unfair use of information which may have been obtained” by

24   company insiders by requiring that “any profit realized by [the

25   insider] from any purchase and sale, or any sale and purchase, of

26   any equity security of such issuer (other than an exempted


                                      6
 1   security) . . . within any period of less than six months . . .

 2   shall inure to and be recoverable by the issuer, irrespective of

 3   any intention on the part of such [insider].”   15 U.S.C. §

 4   78p(b).   Section 16(b) applies to “[e]very person who is directly

 5   or indirectly the beneficial owner of more than 10 percent of any

 6   class of any equity security” of the issuer, id. § 78p(a), and

 7   states that it “shall not be construed to cover any transaction

 8   where [a statutory insider] was not such both at the time of the

 9   purchase and sale, or the sale and purchase, of the security
10   . . . involved,” id. § 78p(b).
11        Section 16(b) is generally subject to mechanical

12   application.   It “‘imposes a form of strict liability’ and

13   requires insiders to disgorge . . . ‘short-swing’ profits ‘even

14   if they did not trade on inside information or intend to profit

15   on the basis of such information.’”    Credit Suisse Sec. (USA) LLC

16   v. Simmonds, 132 S. Ct. 1414, 1417 (2012), quoting Gollust v.

17   Mendell, 501 U.S. 115, 122 (1991); accord Magma Power Co. v. Dow

18   Chem. Co., 136 F.3d 316, 320-21 (2d Cir. 1998) (“No showing of

19   actual misuse of inside information or of unlawful intent is
20   necessary to compel disgorgement.”).   As the Supreme Court has

21   noted, “the only method Congress deemed effective to curb the

22   evils of insider trading was a flat rule taking the profits out

23   of a class of transactions in which the possibility of abuse was
24   believed to be intolerably great.”    Reliance Elec. Co., 404 U.S.
25   at 422.




                                      7
 1         In the past, the customary mechanical application of Section

 2   16(b) was largely saved from arbitrariness because the underlying

 3   rules were discernible and provided predictability.            However, the

 4   growing complexities of financial transactions have generated

 5   numerous issues of statutory interpretation that admit of no

 6   clear resolution.     The courts and the SEC have responded to these

 7   developments in two ways.

 8         First, the Supreme Court has permitted a departure from

 9   “flat rule[s]” in a very limited number of situations.             For

10   example, it has noted that “[t]he statutory definitions of

11   ‘purchase’ and ‘sale’ are broad” and have the potential to “reach

12   many transactions not ordinarily deemed a sale or purchase.”
13   Kern Cnty. Land Co. v. Occidental Petroleum Corp., 411 U.S. 582,
14   593-94 (1973).     Given that breadth, “‘courts have properly asked

15   whether the particular type of transaction involved is one that

16   gives rise to speculative abuse,’” where the instrument or

17   transaction is “unorthodox” or “borderline.”4          Id. at 594-95,

18   quoting Reliance Elec. Co., 404 U.S. at 424 n.4.

19         Second, the SEC has promulgated a substantial number of
20   rules addressing the increasing use of instruments and

21   transactions that do not fit comfortably into Section 16(b)’s

22   simplistic scenario of purchases and sales of common shares.              As

23   explained below, the SEC has promulgated rules governing options

24   of the kind that give rise to the present appeal.


           4
             This approach has been viewed as very limited by some courts. See
     Texas Int’l Airlines v. Nat’l Airlines, Inc. 714 F.2d 533, 539-40 (5th Cir.
     1983)(limiting Kern County to forced sales).

                                           8
 1   b)   SEC Section 16 Rules

 2         A call option is a type of instrument commonly described as

 3   a derivative.5    Because derivative securities are not explicitly

 4   covered by Section 16(b), the SEC adopted Rule 16b-6 in 1991 “to

 5   effect the purposes of section 16 and to address the

 6   proliferation of derivative securities and the popularity of

 7   exchange-traded options.”      Ownership Reports and Trading by

 8   Officers, Directors and Principal Security Holders, Exchange Act

 9   Release No. 34-28869, Investment Company Act Release No.

10   35-25254, 56 Fed. Reg. 7242, 7248 (Feb. 21, 1991).           The adoption

11   was based on the SEC’s conclusion that, because the value of a

12   derivative security is tied to the value of the underlying equity

13   security, “holding derivative securities is functionally

14   equivalent to holding the underlying equity securities for

15   purposes of section 16.”      Trading in derivatives might,
16   therefore, give rise to speculative abuse.6         Id.

17         Appellant seeks to hold Goldman liable under Rule 16b-6(d),

18   quoted in Note 2, supra.      To reiterate, it provides in relevant

19   part that “if an insider writes an option that expires
20   unexercised within six months and profits from doing so on

21   account of having been paid by the purchaser for a right to buy



           5
             Derivatives are “financial instruments that derive their value (hence
     the name) from an underlying security or index.” Magma Power, 136 F.3d at
     321. “An option . . . is a purchased right to buy or sell property at a fixed
     or floating price . . . . A call option gives the option holder the right to
     buy shares of an underlying security at a particular price.” Id. at 321 n.2
     (citations omitted).
           6
             The SEC now defines “equity security” to mean “any equity security or
     derivative security relating to an issuer, whether or not issued by that
     issuer.” 17 C.F.R. § 240.16a-1(d).

                                           9
 1   shares that the purchaser did not exercise, the writer will be

 2   held liable.”   Allaire Corp. v. Okumus, 433 F.3d 248, 252 (2d

 3   Cir. 2006).    The Rule “is designed to prevent a scheme whereby an

 4   insider with inside information favorable to the issuer writes

 5   a[n] . . . option, and receives a premium for doing so, knowing,

 6   by virtue of his inside information, that the option will not be

 7   exercised within six months.”   Gwozdzinsky, 156 F.3d at 309.

 8         As noted, two transactions -- a sale and a purchase of

 9   securities -- are required to trigger liability under Section

10   16(b), and the status as a statutory insider must exist at the
11   time of each transaction.   Reliance Elec. Co., 404 U.S. at 423-
12   25.   Rule 16b-6 defines, for the most part, derivative

13   transactions as either sales or purchases for the purposes of the

14   statute.   These categorizations are premised on the fact that

15   “[j]ust as an insider’s opportunity to profit commences when he

16   purchases or sells the issuer’s common stock, so too the

17   opportunity to profit commences when the insider engages in

18   transactions in options or other derivative securities that

19   provide an opportunity to obtain or dispose of the stock at a
20   fixed price.”   56 Fed. Reg. at 7248.

21         For example, Rule 16b-6(a) provides that “the establishment

22   of or increase in a put equivalent position . . . shall be deemed

23   a sale of the underlying securities for purposes of section 16(b)

24   of the Act.”    17 C.F.R. § 240.16b-6(a).   The definitional section

25   of the regulations explains that writing a fixed-priced call

26   option is functionally the same as taking a “put equivalent


                                      10
 1   position.”   Such “a derivative security position . . . increases

 2   in value as the value of the underlying equity decreases,”

 3   because, when the market price of the security is above but

 4   dropping close to the strike price, the cost to the writer of

 5   selling at the strike price decreases.    17 C.F.R. § 240.16a-1(h).

 6   If the market price falls below the strike price, the option

 7   holder will not exercise it, and the writer will profit on the

 8   premium.   Following the same logic, the regulations provide that

 9   “[t]he closing of a derivative security position as a result of

10   its exercise or conversion shall be exempt from the operation of

11   section 16(b) of the Act.”   17 C.F.R. § 240.16b-6(b).

12        But while Rule 16b-6(a) equates the establishment of a put

13   equivalent position to a sale, Rule 16b-6(d) does not identify

14   the events it lists -- the writing and the expiration of the

15   option -- as either purchases or sales.   However, in a release

16   regarding the then-proposed 1991 Amendments to the Section 16

17   Rules, the SEC stated:   “[a] grant of an option may be viewed as

18   a sale of the derivative security by the writer of the option, if

19   consideration is received for the option.”   Ownership Reports and

20   Trading by Officers, Directors and Principal Stockholders,

21   Exchange Act Release No. 34-26333, 53 Fed. Reg. 49997-02, 50009

22   (Dec. 13, 1988).   In the same release, the SEC noted:   “in the

23   case of an expiration of a short option position, the expiration

24   would be treated as the purchase of the option because there is
25   short-swing profit potential in such a case.”   Id. at 50008.      The

26   SEC advances the same view here in its amicus brief.     Important


                                     11
 1   to our disposition of this appeal, therefore, is the deference we

 2   must give to an agency’s interpretation of its own regulations --

 3   as expressed here in the SEC Release quoted above and in its

 4   amicus brief -- unless the proffered interpretation is “plainly

 5   erroneous or inconsistent with the regulations.”            See Auer v.

 6   Robbins, 519 U.S. 452, 461-63 (1997) (internal quotation marks

 7   omitted); accord Press v. Quick & Reilly, Inc., 218 F.3d 121,

 8   128-29 (2d Cir. 2000).

 9   c)   Application

10         Although neither party contests that the writing of a call
11   option constitutes a sale under Section 16(b), see, e.g.,
12   Gwozdzinsky, 156 F.3d at 309, both challenge the district court’s

13   holding that a short call option’s expiration amounts to a

14   Section 16(b) purchase by the option writer.           The parties claim

15   instead that the passive expiration of a short call option is a

16   statutory nonevent in all cases under the statute; this

17   conclusion, they argue, is compelled by our holdings in Magma

18   Power and Allaire.

19         While the parties agree on this premise, each nevertheless
20   argues for a different outcome.        Acknowledging that two separate

21   transactions are necessary elements of Section 16(b)’s

22   disgorgement requirement, Goldman invites us to invalidate the

23   portion of Rule 16b-6(d) that pertains to short call option
24   expirations.7    Appellant, on the other hand, argues that the

           7
             Of course, Goldman also argues that, if we find that the expiration of
     an option under Rule 16b-6(d) is a Section 16(b) purchase, it cannot be held
     liable because it was no longer a statutory insider at the time of the
     options’ expiration. We agree with that proposition. See infra.

                                           12
 1   writing of a short call option constitutes a simultaneous sale

 2   and purchase under the statute, based on a theory that the writer

 3   commits itself to a subsequent purchase of the underlying stock

 4   at the instant it takes a short position on a call option.

 5   According to appellant, then, because Goldman was a statutory

 6   insider when the options were written -- at the time of the

 7   asserted simultaneous sales and purchases -- for Section 16(b)

 8   purposes, it is of no consequence that Goldman was not a

 9   statutory insider at the time of the option’s expiration.

10        However, both parties misconstrue our precedents, and we

11   adopt the district court’s holding and the SEC’s interpretation:

12   for purposes of Section 16(b), the expiration of a call option

13   within six months of its writing is to be deemed a “purchase” by

14   the option writer to be matched against the “sale” deemed to

15   occur when that option was written.    Rule 16b-6(d) was adopted to

16   eliminate the potential that an insider/option-writer could

17   generate profits by “knowing, by virtue of his inside

18   information, that the option will not be exercised within six
19   months.”   Gwozdzinsky, 156 F.3d at 309.    When an insider sells a
20   call option, and that same option expires unexercised less than

21   six months later, the writer’s opportunity to profit on the

22   underlying stock is realized.   It is for this reason that the SEC

23   determined, “in the case of an expiration of a short option

24   position, the expiration would be treated as the purchase of the

25   option.”   53 Fed. Reg. at 50008.    We follow that resolution of

26   the issue.


                                     13
 1         Neither Magma Power nor Allaire mandates a different result.

 2   In Magma Power, we concluded that an option holder’s decision not

 3   to exercise an option to buy stock does not constitute a

 4   transaction by the option holder for the purposes of the

 5   statute.8   136 F.3d at 324-25.      Goldman is not the option holder,

 6   however, but the option writer.        While the option holder’s

 7   decision not to purchase shares may not constitute a transaction

 8   on the part of the option holder, we have never held as much with

 9   respect to the option writer.
10         Nor does Allaire, an opinion regarding the application of
11   Rule 16b-6(a), control our decision.         In Allaire, the defendants

12   wrote call options on Allaire stock prior to becoming statutory

13   insiders.    Thereafter, the defendants acquired enough shares to

14   push their ownership stake above ten percent.           The original

15   options then expired unexercised (just one month after they were

16   written).    About a month later, while the defendants were still

17   insiders, they wrote a new set of call options on Allaire stock.

18   433 F.3d at 249.

19         Allaire argued that, under Rule 16b-6(a), the expiration of
20   the initial set of options constituted a “purchase” of the stock



           8
             The particular option in Magma Power referenced by the parties was a
     floating-price-option component that was part of a more complex instrument
     (the “Note”), and was retained by the insider after it sold the Note. The
     Note itself included a call option that could be exercised by the Note holder.
     The component the insider retained allowed it, when the Note holder decided to
     exercise its option, either to reacquire shares by paying the Note holder the
     shares’ market value in cash, or to fulfill the Note holder’s call with
     shares. 136 F.3d at 324-25. The insider fulfilled its obligation on the Note
     with shares rather than cash -- that is, deciding not to exercise its option
     to purchase shares. Id. After a thorough analysis, we determined that the
     insider’s decision to not repurchase shares was not the equivalent of a
     purchase under 16b-6(a).

                                           14
 1   because “it represents a liquidation of or decrease in a put

 2   equivalent position”; the second set of options then, when

 3   written, amounted to the establishment of a new put equivalent

 4   position -- a sale that, according to Allaire, could be matched

 5   to the purported purchase.   Id. at 249, 251.   We held that the

 6   expiration of the first set of options did not constitute a

 7   purchase under Section 16b-6(a) matchable to the later sale of a

 8   different set of call options.   Id. at 252.

 9        When read out of that context, there is language in Allaire

10   that would seem in tension with our conclusion that the

11   expiration of a call option under Rule 16b-6(d) constitutes a

12   purchase by the option writer.   But we reiterate, to the extent
13   that Allaire did not make it clear, that this language applies
14   only to short call option expirations under Rule 16b-6(a).

15   Indeed, “[t]he principal issue” in Allaire was “whether, under

16   Rule 16b-6(a), the expiration of a short call option is a

17   purchase, thereby exposing its insider/writer to section 16(b)

18   liability if within six months after that expiration he or she
19   also wrote (sold) another such call option.”    Id. at 251
20   (emphasis added).

21        Given the facts of Allaire, there are sound reasons to view

22   our holding there as limited to call-option expirations under

23   Rule 16b-6(a).   The danger of misuse of non-public information

24   exists at the time the option is written, and the expiration of

25   that option is the moment of profit.   Matching writings with

26   expirations of different options does not clearly advance the


                                      15
 1   purposes of the statute.   Options written at different times are

 2   less likely to give rise to speculative abuse, and matching the

 3   expiration of an option only to its own writing recognizes the

 4   more evident danger.

 5        The Allaire opinion itself makes this clear.   For example,

 6   we observed that, under Rule 16b-6(a), “when the option is

 7   written by the insider (and not canceled), leaving the insider

 8   with no control over whether or not it will be exercised, his or

 9   her inside information, at least in the usual case, cannot be
10   employed for his or her personal profit.”   Id. at 252.   We

11   concluded, “neither the holder’s exercise of the option nor the

12   holder’s allowing the option to expire constitutes a transaction

13   by the option’s writer.”   Id.   Moreover, at several junctures,

14   Allaire was careful to note that its holding applied only to

15   option expirations under Rule 16b-6(a).   See id. (“Just as the

16   holder’s exercise of a call option is not a ‘sale’ by the writer

17   under Rule 16b-6(a), neither is the expiration of a call option a

18   ‘purchase’ by the writer under that provision.” (emphases
19   added)); id. at 253(“If the expiration of a call option were a
20   purchase under Rule 16b-6(a), what purpose would it serve to

21   provide, as Rule 16b-6(d) does, that the expiration of an option

22   within six months of its writing triggers liability?”); id. at

23   254 (“[T]he writing of an option may be a ‘transaction’ under

24   section 16(b) but . . . the expiration of an option, when matched

25   against any transaction other than its own writing, is not.”

26   (emphasis added)).


                                      16
 1         Allaire’s express and implied references to Rule 16b-6(d),

 2   therefore, beg the question we answer:          when matched against its

 3   own writing, the expiration of an option within six months is a

 4   “transaction” -- a purchase by the option writer -- for the

 5   purposes of Section 16(b).

 6         Appellant’s theory -- that the writing of an option

 7   constitutes a simultaneous purchase and sale -- finds support

 8   neither in the statutory text, the SEC Rules, nor in our

 9   precedents.    Section 16(b) plainly requires separate

10   transactions.

11         To the extent appellant argues that the broad, statutory

12   definitions of “purchase” and “sale” encompass the circumstances

13   here -- essentially that both definitions should apply to the

14   transaction that occurs when the option is written to effectuate

15   the purposes of the statute -- that argument is contrary to the

16   statutory text, which is clearly addressed to separate

17   transactions.     Moreover, it ignores the real possibility that the

18   holder will exercise the option.           Most importantly, the SEC

19   undertook this identical inquiry when it promulgated Rules

20   establishing that there are two relevant transactions at separate
21   points in time:     the writing of the option and its expiration.9


           9
             Appellant cites to several district court cases in support of his
     simultaneous purchase and sale theory, none of which are persuasive. See,
     e.g., Matas v. Siess, 467 F. Supp. 217 (S.D.N.Y. 1979) (exercise of stock
     appreciation rights for cash under company plan was an unorthodox transaction
     that the court treated as both a purchase and sale for purposes of Section
     16(b), where defendants timed the exercise to maximize the
     difference, which they received in cash, between the option price
     and the market price on the date of exercise).


                                           17
 1         While the SEC’s resolution may not be the only reasonable

 2   one, it is certainly within the realm of reason, and we defer to

 3   it.   Press, 218 F.3d at 128-29.    Section 16(b) was written to

 4   govern a financial world of largely square pegs and square holes.

 5   The growing use of oval, rectangular, triangular, star-like, etc.

 6   pegs, creates problems without clear solutions.    We are not free

 7   to reject the SEC’s view as to the most desirable, if not

 8   perfect, solution to particular issues.

 9         In that regard, appellant warns of the dangers associated

10   with the holding we now adopt, cautioning that a statutory

11   insider can simply write an option and then divest himself of

12   shares enough that he is no longer subject to Section 16(b)’s

13   disgorgement requirements.   However, this argument is foreclosed
14   by Reliance Electric, which allowed a statutory insider to
15   purposefully drop its holdings to slightly under ten percent so

16   as to sell the remainder without liability under Section 16(b).

17   When it enacted Section 16(b), “Congress did not reach every

18   transaction in which an investor actually relies on inside
19   information.”   Reliance Elec. Co., 404 U.S. at 422.    For example,
20   the statute “clearly contemplates that a statutory insider might

21   sell enough shares to bring his holdings below ten percent, and

22   later -- but still within six months -- sell additional shares

23   free from liability under the statute,” id. at 423, creating the

24   very situation of which appellant calls upon us to be

25   apprehensive.   As in the case of structured transactions designed

26   to drop below ten percent, we must also follow the instruction


                                        18
 1   that “[l]iability cannot be imposed simply because the investor

 2   structured his transaction with the intent of avoiding liability

 3   under [Section] 16(b).”   Id. at 422.

 4        The prophylactic disgorgement rule of Section 16(b) is not

 5   an all-encompassing remedy for every occasion when insiders

 6   succeed in writing options and disposing of stock in a way that

 7   allows a profit based on inside information.    Section 16(b)

 8   requires that a statutory insider must have such status at the

 9   time of the sale and the purchase of securities in order to be

10   liable.   Therefore, to be liable, Goldman had to have been a

11   statutory insider both at the time of the option’s writing and at

12   the time of its expiration.    Because Goldman was no longer a

13   statutory insider at the time the options expired in January

14   2010, it is not liable.

15                                 CONCLUSION

16   To summarize:

17        (1) For purposes of Section 16(b), the expiration of a call

18   option within six months of its writing is to be deemed a

19   “purchase” by the option writer to be matched against the “sale”

20   deemed to occur when that option was written.

21        (2) Section 16(b) requires statutory insider status at the

22   time of both purchase and sale, and so Goldman was not required

23   to disgorge profits where it was a statutory insider only when

24   the options were written, but not when they expired.

25        For the reasons stated above, we affirm the June 8, 2012,

26   judgment of the district court.


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