Roth v. The Goldman Sachs Group, Inc. , 740 F.3d 865 ( 2014 )


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  •      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.
    19