United States v. Rivera-Izquierdo , 850 F.3d 38 ( 2017 )


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  •           United States Court of Appeals
    For the First Circuit
    No. 15-1620
    UNITED STATES OF AMERICA,
    Appellee,
    v.
    JORGE RIVERA-IZQUIERDO,
    Defendant, Appellant.
    APPEAL FROM THE UNITED STATES DISTRICT COURT
    FOR THE DISTRICT OF PUERTO RICO
    [Hon. Carmen Consuelo Cerezo, U.S. District Judge]
    Before
    Barron, Stahl, and Lipez,
    Circuit Judges.
    David Shaughnessy for appellant.
    James I. Pearce, Attorney, Appellate Section, Criminal
    Division, U.S. Department of Justice, with whom Leslie R. Caldwell,
    Assistant Attorney General, Criminal Division, Sung-Hee Suh,
    Deputy Assistant Attorney General, Criminal Division, Wifredo A.
    Ferrer, United States Attorney, Southern District of Florida,
    Charles R. Walsh, Trial Attorney, Criminal Division, and Luke Cass,
    Trial Attorney, Criminal Division, were on brief, for appellee.
    March 6, 2017
    BARRON, Circuit Judge.           In 2014, a jury convicted Jorge
    Rivera-Izquierdo ("Rivera") of two counts of money laundering, in
    violation of 18 U.S.C. §§ 1957 and 2.                He now appeals.    Finding no
    reversible error, we affirm.
    I.
    18 U.S.C. § 1957 makes it a felony to "knowingly engage[]
    or attempt[] to engage in a monetary transaction in criminally
    derived property of a value greater than $10,000 and is derived
    from specified unlawful activity."                 18 U.S.C. § 1957(a) (emphasis
    added).      The    statute    goes   on      to    define   "criminally   derived
    property" as follows: "any property constituting, or derived from,
    proceeds obtained from a criminal offense."                  
    Id. § 1957(f)(2).
    In    2010,   a   federal     indictment        charged   Rivera   with
    violating 18 U.S.C. § 1957 and 18 U.S.C. § 2, which punishes aiders
    and abettors as though they were principals.                     According to the
    indictment, Rivera and several co-defendants, "aiding and abetting
    each other, did knowingly engage or attempt to engage in" two
    transactions to purchase cars with "criminally derived property of
    a value greater than $10,000 and is derived from specified unlawful
    activity."
    The indictment alleged that the two vehicle purchases
    occurred in September 2008 and May 2009, respectively.                           The
    "specified unlawful activity" was a fraudulent scheme perpetrated
    - 2 -
    by   Rosa      Castrillon-Sanchez      ("Castrillon"),        the   daughter   of
    Rivera's common-law wife.1
    According to the indictment, in September 2008, Rivera
    and Castrillon used "criminally derived" funds from Castrillon's
    fraudulent scheme to make a down payment of $20,000 for a 2008
    Toyota Sequoia sport utility vehicle.            In addition, several months
    later, Rivera again helped Castrillon purchase a sport utility
    vehicle -- this time, a BMW -- by making a "[p]ayment toward" the
    vehicle's purchase price of approximately $63,418 with funds in
    excess of $10,000 that were "criminally derived" from Castrillon's
    fraudulent scheme.
    The indictment described Castrillon's fraudulent scheme
    as follows.       Castrillon would tell her victims, most of whom were
    friends and family members, that a large sum of money -- for which
    she was the ostensible beneficiary -- had been "frozen" in a local
    bank.       Castrillon would then request money to help "release" these
    "frozen" funds.          The victims could not afford the large sums of
    money       Castrillon    requested.   She     thus   would    either   complete
    fraudulent loan applications on behalf of her victims or instruct
    1
    Subsection (f)(3) provides that the term "specified unlawful
    activity" is to be given the meaning that term has in 18 U.S.C.
    § 1956(c)(7). The parties do not dispute that Castrillon's scheme
    -- for which she was charged with violating 18 U.S.C. § 1028, the
    federal identity fraud statute, 18 U.S.C. § 1343, the federal wire
    fraud statute, and 18 U.S.C. § 1344, the federal bank fraud statute
    -- qualifies as specified unlawful activity under § 1957. See 18
    U.S.C. §§ 1957(f)(3), 1956(c)(7), 1961.
    - 3 -
    them to take out loans themselves.     Castrillon would then take the
    cash from those loans.   All told, Castrillon defrauded her victims
    out of millions of dollars.
    At trial, Rivera introduced evidence that Castrillon
    gambled extensively and that she used money taken from her gambling
    winnings -- rather than from the money that she had taken from the
    fraud victims -- to supply the funds that Rivera then used to make
    the car purchases.   Rivera thus contended that, because the money
    that he used in buying the cars came from the gambling winnings,
    it was not "criminally derived property."     Rivera also argued that
    he did not know that the funds that he received from Castrillon
    and that he then used in buying the cars constituted "criminally
    derived property," even if those funds somehow were so derived.
    Instead, he argued, he thought that the funds that Castrillon gave
    him were just funds that she took from her gambling winnings.
    In response, the government sought to show at trial that
    the money from the gambling winnings actually did constitute
    "criminally derived property."    The government did so by putting
    in evidence that Castrillon had used the money that she took from
    her fraud victims to fund her gambling.      The government also put
    forward evidence to show that Rivera knew that Castrillon had done
    so.
    After a month-long trial, the jury convicted Rivera of
    two counts of money laundering, in violation of 18 U.S.C. §§ 1957
    - 4 -
    and 2.       The jury acquitted him, however, of the two other counts
    that    he    faced:   conspiracy     to    commit     bank    and   wire    fraud   in
    violation of 18 U.S.C. § 1349, and wire fraud, in violation of 18
    U.S.C. § 1343.
    The District Court sentenced Rivera to 42 months of
    imprisonment.       On appeal, Rivera makes a number of challenges to
    his convictions.        We consider each one in turn.
    II.
    We start with the challenge that is the primary focus of
    the parties: Rivera's contention that the District Court erred in
    instructing the jury regarding one part of § 1957.                     We find that
    this challenge has no merit.
    A.
    The District Court instructed the jury that, just as
    § 1957(f)(2) provides, the term "'criminally derived property'
    means    any     property    constituting,        or   derived       from,    proceeds
    obtained from a criminal offense."               Rivera does not challenge this
    instruction.           He   instead    challenges        the    instruction        that
    immediately       followed,    which       purported     to     define       the   term
    "proceeds" in the statute's definition of "criminally derived
    property."
    That instruction informed the jury that "proceeds" were:
    "any property derived from or obtained or retained, directly or
    indirectly, through some form of unlawful activity, including the
    - 5 -
    gross receipts of such activity."      Rivera points out that this
    instruction tracked, word for word, the definition of "proceeds"
    that Congress set forth in an amendment to § 1957, which became
    law in 2009 as part of the Fraud Enforcement and Recovery Act of
    2009 ("FERA"), Pub. L. 111-21, 123 Stat. 1617.      Rivera contends
    that, under the Ex Post Facto Clause, this definition of "proceeds"
    could not lawfully have been applied to his case because the
    "specified   unlawful   activity"     --   Castrillon's   fraudulent
    scheme -- had begun years before FERA's passage.2
    2 Among other things, FERA defined "proceeds" in the companion
    money-laundering statute, 18 U.S.C. § 1956, to encompass "any
    property derived from or obtained or retained, directly or
    indirectly, through some form of unlawful activity, including the
    gross receipts of such activity."      18 U.S.C. § 1956(c)(9) (as
    amended).    FERA then also expressly provided that the term
    "proceeds" used in the definition of "criminally derived property"
    in § 1957 "shall have the meaning given ['proceeds'] in section
    1956." 18 U.S.C. § 1957(f)(3) (as amended). The definition of
    "criminally derived property" in subsection (f)(2) of § 1957,
    however, has not been modified since the statute's passage in 1986.
    See Anti-Drug Abuse Act of 1986, Pub. L. 99-570, § 1352, 100 Stat.
    3207.
    We note that the simple insertion of the new, post-FERA,
    definition of "proceeds" from § 1956(c)(9) into § 1957(f)(2)
    appears to lead to a strange result: "The term 'criminally derived
    property' means any property constituting, or derived from, any
    property derived from or obtained or retained, directly or
    indirectly, through some form of unlawful activity, including the
    gross receipts of such activity, obtained from a criminal offense."
    Thus, we think Congress likely intended for the definition of
    "criminally derived property" in subsection (f)(2) to read
    something like the following: "the term 'criminally derived
    property' means any property constituting or derived from,
    proceeds, obtained from a criminal offense, including the gross
    receipts of such activity." See S. Rep. No. 111-10, at 8 (2009)
    (explaining that because Santos "mistakenly limited the term
    'proceeds' to the 'profits' of a crime," FERA was designed to
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    Rivera goes on to argue that the instruction was more
    "expansive and elastic" than the pre-FERA definition of "proceeds"
    that the District Court should have used.          To make this argument,
    Rivera    first   directs   our   attention   to   the    companion   money-
    laundering statute to § 1957, which is 18 U.S.C. § 1956.3
    Prior to FERA's passage, Rivera notes, that statute --
    like § 1957 -- did not define the word "proceeds."           There was thus
    no reason to conclude that "proceeds" in § 1956 meant anything
    other than what that word meant in § 1957.               This fact matters,
    Rivera argues, because, in 2008, in United States v. Santos, 
    553 U.S. 507
    (2008), the Supreme Court narrowly construed the word
    "amend the criminal money laundering statutes . . . to make clear
    that the proceeds of specified unlawful activity include the gross
    receipts of the illegal activity, not just the profits from the
    illegal activity"); see also 155 Cong. Rec. S4774-02 (daily ed.
    Apr. 28, 2009) (statement of Sen. Levin) ("[R]ecent court decisions
    have misdefined the term 'proceeds' from the money laundering
    statute   to   mean   only   the   net   receipts   from   unlawful
    activities . . . This act will fix these decisions and explicitly
    define 'proceeds' to include not only net but gross receipts from
    unlawful activities.").
    3   Prior to 2009, § 1956 provided:
    Whoever, knowing that the property involved in a
    financial transaction represents the proceeds of some
    form of unlawful activity, conducts or attempts to
    conduct such a financial transaction which in fact
    involves the proceeds of specified unlawful activity--
    (A) with the intent to promote the carrying on of
    specified unlawful activity . . . shall be sentenced to
    . . . imprisonment for not more than twenty years.
    Anti-Drug Abuse Act § 1352 (emphasis added).
    - 7 -
    "proceeds" in § 1956 and thus, according to Rivera, necessarily
    also set forth the same narrow construction of that word in § 1957.4
    Specifically, according to Rivera, Santos made clear
    that "proceeds" meant only the net receipts (or, put otherwise,
    the profits) of specified unlawful activity and not the gross
    receipts of that activity.         Rivera also contends that Santos made
    clear that, in any event, "proceeds" (whether gross or net) never
    means       "more   than   the   receipts   from   the   specified   criminal
    activity."5
    4
    In Santos, the Court considered whether the expenses of
    operating the defendant's "illegal lottery" -- including "payments
    to runners, winners, and collectors" -- constituted "proceeds"
    under 8 U.S.C. § 
    1956. 553 U.S. at 510
    . A four-justice plurality
    concluded that they did not. Because, on the plurality's view,
    the meaning of the term "proceeds" was ambiguous, the plurality
    applied the rule of lenity to hold that the term "proceeds" means
    the "net profits" of criminal activity, and thus did not encompass
    the illegal lottery's expenses. 
    Id. at 514.
    Concurring in the
    judgment, Justice Stevens declined to adopt a categorical
    definition, instead suggesting that the "Court need not pick a
    single definition of 'proceeds' applicable to every unlawful
    activity."   
    Id. at 525.
       Like the plurality, however, Justice
    Stevens was concerned that applying a "gross receipts" definition
    to the specific facts of Santos would lead to the so-called
    "merger" problem," whereby the defendant would be convicted of the
    substantive offense of "operating a gambling business," and then
    convicted again, under § 1956, of money laundering for "the mere
    payment of the expense of operating an illegal gambling business."
    
    Id. at 527.
       This possibility, Justice Stevens noted, was "in
    practical effect tantamount to double jeopardy." 
    Id. Applying the
    rule of Marks v. United States, 
    430 U.S. 188
    (1977), we held
    in United States v. Adorno-Molina, 
    774 F.3d 116
    , 123 (1st Cir.
    2014), that "Justice Stevens's concurrence is the controlling
    law."
    5
    Although Castrillon's fraud began several years before
    Santos was decided, Rivera does not contend that the definition of
    - 8 -
    From this premise, Rivera contends that the District
    Court's instruction, by relying on FERA's later-enacted definition
    of "proceeds," expanded the scope that Santos had given to that
    term in § 1956 in two key respects.            Unlike the definition of
    "proceeds" set forth in Santos, Rivera points out, the instruction
    -- tracking FERA -- expressly stated both that "proceeds" includes
    "gross   receipts"   and   that   "proceeds"   includes:   "any   property
    derived from or obtained or retained, directly or indirectly,
    through some form of unlawful activity."         18 U.S.C. § 1956(c)(9)
    (as amended) (emphasis added).
    In pressing this challenge, Rivera emphasizes that the
    government first proposed this instruction as to the meaning of
    "proceeds" only after Castrillon had testified for the defense
    about her gambling activity.      During that testimony, Rivera notes,
    Castrillon stated that the money that she gave to Rivera to
    purchase the cars came from her gambling winnings. Rivera contends
    that the government proposed the FERA-based instruction defining
    "proceeds" in order to argue to the jury that it was "simply
    irrelevant whether the money" used to buy the cars was "gambling
    winnings or fraud proceeds because Rivera was guilty either way."
    As a result, he argues, the instructional error "went to the very
    heart of the case."        It impermissibly enabled the jury, Rivera
    the term should be anything other than one that he contends that
    Santos provided.
    - 9 -
    contends, to find that Castrillon's gambling winnings constituted
    the "proceeds" of "specified unlawful activity," even though those
    winnings were not the actual funds taken from Castrillon's fraud
    victims and thus were not (in Rivera's view) the "proceeds" of
    that fraud under Santos.
    B.
    Rivera concedes that he did not object at trial to the
    jury instruction that he now challenges on appeal.     Our review,
    therefore, is only for plain error.
    Under this standard, Rivera "faces the 'heavy burden of
    showing (1) that an error occurred; (2) that the error was clear
    or obvious; (3) that the error affected his substantial rights;
    and (4) that the error also seriously impaired the fairness,
    integrity, or public reputation of judicial proceedings.'"   United
    States v. Prieto, 
    812 F.3d 6
    , 17 (1st Cir. 2016) (quoting United
    States v. Riccio, 
    529 F.3d 40
    , 46 (1st Cir. 2008)).     Assuming a
    clear or obvious instructional error, Rivera need not, under the
    third prong of the plain-error review standard, "prove by a
    preponderance of the evidence that but for [the] error things would
    have been different."   United States v. Rodríguez, 
    735 F.3d 1
    , 11-
    12 (1st Cir. 2013) (quoting United States v. Dominguez Benitez,
    
    542 U.S. 74
    , 84 n.9 (2004) (insertion in original)).         But, a
    showing of "mere possibilities [is] not enough" to prove that an
    instructional error affected a defendant's substantial rights.
    - 10 -
    United States v. Procopio, 
    88 F.3d 21
    , 31 (1st Cir. 1996).           Rivera
    thus must show that the "outcome of the case would likely have
    changed" had the erroneous instruction not been given.               United
    States v. Colon, 
    744 F.3d 752
    , 758 (1st Cir. 2014).
    The government disputes whether Rivera is right that the
    District Court erred in basing the "proceeds" instruction on the
    definition of the term that FERA set forth, given when FERA became
    law.   The government also disputes whether he is right about how
    narrowly Santos construed "proceeds."        Cf. 
    Santos, 553 U.S. at 525
    (Stevens, J., concurring in judgment). But even if Rivera is right
    on both counts, his challenge to the instruction still fails
    because he cannot show that the instruction likely affected the
    outcome of the case.
    The record makes clear that the part of the instruction
    that defined "proceeds" to include "gross receipts" did not likely
    affect the outcome of the case. The record shows that Castrillon's
    fraud entailed little in the way of expenses.               The record also
    shows that the gross receipts from the fraud were extremely large
    -- totaling more than $2.5 million.          The expenses of the fraud,
    therefore, were simply too paltry for the instruction's definition
    of   "proceeds"   to   include   "gross    receipts"   to   have   made   any
    difference.   Nor does Rivera point to anything in the record to
    suggest otherwise.
    - 11 -
    The   record     similarly    shows    that    the    part   of    the
    instruction that defined "proceeds" by using what Rivera calls
    "expansive and elastic" words -- "any property derived from or
    obtained or retained, directly or indirectly" -- did not likely
    affect the outcome of the case.           (emphasis added).          As we have
    noted, the instructions as a whole made clear that, consistent
    with § 1957(f)(2), property "derived from" the "proceeds" of
    specified   unlawfully       activity    is    itself   "criminally      derived
    property." United States v. Brown, 
    669 F.3d 10
    , 29 (1st Cir. 2012)
    ("When applying the plain error standard in the context of jury
    instructions, 'we look at the instructions as a whole to ascertain
    the extent to which they adequately explain the law without
    confusing or misleading the jury.'"              (quoting United States v.
    Troy, 
    618 F.3d 27
    , 33 (1st Cir. 2010))).
    Thus,   the    government     did    not    need    to   prove    that
    Castrillon's      gambling     winnings       themselves       constituted     the
    "proceeds" of her fraud.        To make the case that Rivera, in using
    money taken from those winnings to buy the cars, used "criminally
    derived property," the government needed to prove only that the
    money that he used from the gambling winnings constituted property
    "derived from" the fraud's "proceeds."
    This feature of the definition of "criminally derived
    property" dooms Rivera's challenge to the instruction.                       As we
    explain more fully in addressing Rivera's separate challenge to
    - 12 -
    the sufficiency of the evidence, the record provides ample support
    for a jury to find that Castrillon generated her gambling winnings
    exclusively from the funds that she took from the fraud (or, put
    otherwise, from the "proceeds" of it).          The record also provides
    ample support for a jury to find that the fraudulently obtained
    funds that Castrillon used to generate the gambling winnings
    totaled at least as much as the amount of money that Castrillon
    then gave to Rivera to buy the cars.           Given the strength of the
    evidence that Castrillon's gambling winnings were "derived from"
    the proceeds of Castrillon's fraud -- and thus that the proceeds
    were "criminally derived" -- Rivera fails to show that the outcome
    of   the   case   would   likely   have     changed   had   the   challenged
    instruction on "proceeds" not been given.6
    6A number of sister circuits, pre-FERA, had construed the
    "derived from" portion of the statute's definition of "criminally
    derived property" expansively in analogous circumstances.      And
    they did so to account for the practical reality that "[m]oney is
    fungible," and thus that "when funds obtained from unlawful
    activity have been combined with funds from lawful activity into
    a single asset, the illicitly-acquired funds and the legitimately-
    acquired funds (or the respective portions of the property
    purchased with each) cannot be distinguished from each other."
    United States v. Moore, 
    27 F.3d 969
    , 976-77 (4th Cir. 1994); see
    also 
    id. (concluding that,
    where the defendant obtained the
    "overwhelming bulk of the purchase money" for several condominiums
    from his bank fraud, "the jury was entitled to conclude . . . that
    when the condominiums were eventually sold, the net proceeds of
    that sale were in their entirety property derived from . . . [the
    defendant's] bank fraud" (emphasis added)); United States v.
    Johnson, 
    971 F.2d 562
    , 570 (10th Cir. 1992) ("An examination of
    the defendant's bank records gave no indication that the funds in
    the defendant's account came from any source other than investors
    in the alleged [fraud scheme].      Under the circumstances, the
    - 13 -
    Rivera, moreover, makes no developed argument to the
    contrary.   He instead focuses solely on how the jury instruction's
    "expansive and elastic" language defining "proceeds" permitted the
    jury to find that the gambling winnings were "proceeds."   But, as
    we have just explained, that focus is too limited, given how § 1957
    defines "criminally derived property."      See United States v.
    Zannino, 
    895 F.2d 1
    , 17 (1st Cir. 1990) ("[I]ssues adverted to in
    a perfunctory manner, unaccompanied by some effort at developed
    argumentation, are deemed waived.").7
    evidence was sufficient for the jury to find that the funds
    withdrawn were derived from the specified unlawful activity."
    (emphasis added)); cf. United States v. Davis, 
    226 F.3d 346
    , 357
    (5th Cir. 2000) ("[W]hen the aggregate amount withdrawn from an
    account containing commingled funds exceeds the clean funds,
    individual withdrawals may be said to be of tainted money, even if
    a particular withdrawal was less than the amount of clean money in
    the account.").
    7 We thus have no need to address whether the instruction
    would have been prejudicial if we were, like Rivera, to focus only
    on the meaning of "proceeds." We do note that it is not at all
    clear that it was. Rivera does contend that Santos makes clear
    that the funds used to purchase cars, insofar as they are from
    gambling winnings, would not qualify as "proceeds" even if they
    would qualify under FERA's more expansive definition. But Santos
    considered only whether the "proceeds" of the defendant's illegal
    lottery referred to the "receipts" of that lottery, or its
    
    "profits." 553 U.S. at 511
    (Scalia, J., plurality opinion). Thus,
    Santos did not address how tight the connection between a
    transaction charged under § 1957 and some specified unlawful
    activity must be in order for the funds used to make the
    transaction to "constitute" the "proceeds" of that activity. See
    18 U.S.C. § 1957(f)(2). Moreover, some courts, pre-FERA, indicated
    that "proceeds" was even then an expansive term. See 
    Moore, 27 F.3d at 976-77
    ("[W]hen funds obtained from unlawful activity have
    been combined with funds from lawful activity into a single asset
    . . . it may be presumed . . . that the transacted funds, at least
    up to the full amount originally derived from crime, were the
    - 14 -
    Accordingly, we conclude that Rivera's challenge to the
    jury instruction concerning the definition of the term "proceeds"
    in § 1957 fails.    For even if the instruction was given in error,
    Rivera has not shown how that error affected his substantial
    rights.
    III.
    We turn, then, to Rivera's contention that the evidence
    was insufficient.    Our review is de novo.   United States v. Maymí-
    Maysonet, 
    812 F.3d 233
    , 236 (1st Cir. 2016).       In undertaking that
    review, we consider "the evidence, both direct and circumstantial,
    in the light most favorable to the prosecution and decide whether
    that evidence, including all plausible inferences drawn therefrom,
    would allow a rational factfinder to conclude beyond a reasonable
    doubt that the defendant committed the charged crime."               
    Id. (quoting United
    States v. Cruz-Rodriguez, 
    541 F.3d 19
    , 26 (1st
    Cir.   2008)).     Applying   these   standards,   we   reject   Rivera's
    sufficiency challenge, which, as we will explain, has two distinct
    aspects.
    proceeds of the criminal activity or derived from that activity."
    (emphasis added)); see also United States v. Sokolow, 
    91 F.3d 396
    ,
    409 (3d Cir. 1996) ("It is clear from the full context of the
    district judge's explanation of the concept of proceeds that he is
    addressing the absence of a legal requirement that the government
    trace the funds constituting criminal proceeds when they are
    commingled with funds obtained from legitimate sources. We find
    no error in the district court's jury instructions in this regard."
    (emphasis added) (internal citation omitted)).
    - 15 -
    A.
    First,    Rivera   argues    that   the   government   presented
    insufficient evidence to prove beyond a reasonable doubt that the
    money that he used to purchase the two vehicles was "criminally
    derived property."    But, we do not agree.         See United States v.
    Rodríguez-Durán, 
    507 F.3d 749
    , 758 (1st Cir. 2007) (explaining
    that on sufficiency review the "government need not succeed in
    eliminating every possibly theory consistent with the defendant's
    innocence" (internal quotation marks and citation omitted)).
    The government adduced a wealth of evidence that showed
    that   Castrillon    generated   the    gambling     winnings    by   using
    fraudulent funds in an amount far greater than the amount that she
    testified that she gave to Rivera to make each car purchase.
    Specifically, Castrillon testified that she obtained more than
    $2.5 million from the victims of her fraud, which began in 2005.
    Moreover, Castrillon testified that she "began [her gambling]
    addiction, it was for five years, 2006 [or] 2005"; that, as of
    2007, her income from her prior employment had come to an end; and
    that, over time, she suffered gambling losses of "much more" than
    half a million dollars.
    A jury could thus reasonably infer that the source of
    the money that Castrillon used to generate the gambling winnings
    was exclusively the money that Castrillon took from the "proceeds"
    of the fraud.   A jury could also reasonably infer that the amount
    - 16 -
    of fraudulently obtained funds she used to fund her gambling
    totaled at least as much as the amount of money that she gave to
    Rivera to buy the cars.     And, for the reasons that we have just
    explained regarding the scope of the "derived from" prong of
    § 1957's definition of "criminally derived property," a jury that
    could reasonably make those inferences also could reasonably find
    the following.     Insofar as Rivera used the gambling winnings to
    make each car purchase that is at issue here, he each time used
    "criminally derived property" in excess of $10,000 from "specified
    unlawful activity" to do so.
    To make the contrary case, Rivera advances a number of
    arguments about the state of the record.       But we do not find them
    to be persuasive.
    Rivera    first   contends    that   it   is   possible   that
    Castrillon made money from gambling before the fraud began in 2005.
    He thus argues that a jury reasonably could have found that Rivera
    made the car purchases with funds taken from these pre-fraud,
    untainted gambling winnings.    But, Rivera identifies no plausible
    source -- nor do we find one in the record -- for Castrillon's
    hypothetically untainted gambling winnings, let alone evidence
    that such untainted winnings were of a size sufficient to supply
    more than $10,000 towards a car purchase not once, but twice.
    To the contrary, by her own testimony, Castrillon began
    gambling "in 2006, [or] 2005," and she did not testify that the
    - 17 -
    gambling preceded the fraud.           Nor did she at any point testify
    that her pre-fraud gambling luck (if any she had) generated amounts
    of any significance.        In fact, Castrillon made clear that she used
    the fraudulently obtained funds to feed her casino gambling in the
    down periods, which she also testified were frequent enough (or
    unlucky enough) that Castrillon's gambling losses at a San Juan
    hotel's casino well exceeded half a million dollars.
    Rivera    next    notes    that,   at   one   point     during   her
    testimony, Castrillon stated that the funds that Rivera used to
    buy the BMW came from money that she made off of the "electronic
    lottery."   And, Rivera contends, a jury reasonably could find that
    the lottery winnings were not tainted by the fraud.
    Rivera never identifies evidence in the record, however,
    that reveals an untainted source of the funds that Castrillon might
    have tapped to play the electronic lottery.               Nor did Castrillon
    herself identify one.        Rather, Castrillon, as we have just noted,
    testified   that     she   had   no   source   of   income   from    her   prior
    employment after 2007 and that she had casino gambling losses in
    excess of $500,000.        She also agreed during her testimony at trial
    that the "money [she] would gamble with . . . was from" her fraud
    victims, which funds totaled more than $2.5 million.8
    8  The full colloquy surrounding that statement during
    Castrillon's cross-examination by the government reads as follows:
    - 18 -
    Finally, Rivera points to the gap in time between late
    October 2008, when Castrillon received the last of the funds she
    took directly from the fraudulent scheme, and May 2009, when the
    second vehicle was purchased.    But Rivera identifies no plausible
    separate source of funds -- that is, funds that were not "derived
    from" the "proceeds" of the fraud scheme -- with which Castrillon
    might have gambled after the scheme ended and from which the funds
    used to pay for the cars could have come.   We thus do not see how
    this gap helps Rivera's argument.
    That leaves only the circuit precedents that Rivera
    relies upon.   But, given the evidence in the record, these cases
    are readily distinguished.
    A: Are you asking me, sir, if the money that I used to
    pay for the [Toyota Sequoia], I never thought about
    paying it back to other people?
    Q: That's pretty obvious; isn't it?
    A: The answer to that is no.
    Q: And you testified that -- in direct, that that money
    was from casino winnings?
    A: Yes, there was evidence to that effect and I had to
    present it.    Not the casino, it was the electronic
    lottery.
    Q: The money you would gamble with, as you testified
    before, was from the individuals who were loaning you
    money?
    A: And the money that I would also, at the same time,
    win at the machines.
    In answering the prosecutor's question, Castrillon clearly did not
    distinguish between casino gambling and the electronic lottery,
    thus suggesting she also used fraudulently derived funds to play
    the lottery.
    - 19 -
    The first precedent Rivera relies on is our decision in
    United States v. Carucci, 
    364 F.3d 339
    (1st Cir. 2004).             There,
    the government sought to prove that the defendant was guilty of
    violating § 1957 because he had laundered funds derived from the
    criminal activities of Stephen Flemmi, "the notorious leader of
    Boston's 'Winter Hill Gang.'"        
    Id. at 340.
        We explained that, in
    light   of   the    record,    "[a]ccepting   that   Flemmi's   income   was
    illegitimate, it could have been linked to any number of criminal
    activities . . . [and thus] there [was] no . . . evidence that
    Flemmi had engaged in the specified [unlawful activities charged
    in the indictment] in the relevant time period."          
    Id. at 347.
    Rivera's case is very different.        The record here does
    not reveal plausible sources for the money that Rivera used to
    help Castrillon buy the two cars other than the gambling winnings
    that the record sufficiently shows were "derived from" the proceeds
    of her fraud.      Instead, the evidence offers no plausible untainted
    source form which the gambling winnings were made.
    Similarly off-point is United States v. Wright, 
    651 F.3d 764
    (7th Cir. 2011).          There, the Seventh Circuit held that the
    government failed to prove a violation of § 1957 because the
    defendant used only $8,000 in "drug proceeds" -- an amount below
    the statute's $10,000 threshold for the amount that must be
    involved in a transaction charged under § 1957 -- to purchase a
    property that the defendant later sold for approximately $50,000.
    - 20 -
    
    Id. at 771.
          In Rivera's case, however, the government did not
    rely on the value of the assets purchased (the cars) to get over
    the   statutorily    imposed     $10,000-per-transaction          threshold     for
    "criminally derived property."            The government instead relied on
    extensive     evidence   that    showed    the    following.       The   gambling
    winnings came exclusively from the funds that Castrillon took from
    her fraud.     And, the fraudulently obtained funds that she used to
    gamble totaled well in excess of the amount of money that would
    have been needed to cover the money that Rivera got from Castrillon
    to buy the cars, which exceeded $10,000 per transaction.
    For related reasons, United States v. Rutgard, 
    116 F.3d 1270
    (9th Cir. 1997), is also no help to Rivera.                There, the Ninth
    Circuit   held    that   money     derived       from   funds   that     were   not
    "criminally derived property" and that were sufficient to pay for
    a transaction in excess of $10,000 does not become "criminally
    derived" just because the clean funds are commingled in an account
    that also contains "criminally derived property."                  
    Id. at 1292;
    see also Saccoccia v. United States, 42 Fed. Appx. 476, 481 (1st
    Cir. 2002).      But here, the record overwhelmingly indicates that
    only funds that were, at the least, "derived from" the proceeds of
    the fraud were used to give Rivera the funds that he used to buy
    the   cars.      Thus,   the    circumstance      Rutgard   addressed      is   not
    presented here.
    - 21 -
    B.
    The     other   aspect    of    Rivera's     sufficiency    challenge
    concerns the evidence of his mens rea.                   He argues that the
    government presented insufficient evidence to prove that he "knew
    that more than $10,000 of criminal money was involved" in the
    second   vehicle    purchase.        (emphasis    added).       He    bases   this
    contention on Castrillon's testimony that she told him that "the
    money for the car was gambling winnings."
    The record, however, reveals evidence of Rivera's close
    ties to Castrillon -- including her testimony that it was "[a]s if
    he was" her father.          Rivera also concedes that the government
    presented wide-ranging evidence of Rivera's participation in the
    fraud scheme, including evidence that he recruited new victims,
    pressured them to take out loans, assured them the frozen funds at
    the heart of the scheme were real, and threatened victims who came
    to complain to Castrillon's mother.
    Thus, a jury could reasonably infer that Rivera knew
    that Castrillon had no source of revenue for her gambling activity
    other than the fraudulently obtained funds and that he knew that
    the fraudulent scheme was extremely profitable -- generating, per
    Castrillon's testimony, over $2.5 million.              And a jury that could
    reasonably make this inference could also reasonably infer that
    Rivera   knew    that      money    obtained     from    that   scheme    funded
    Castrillon's gambling and, consequently, that the funds she took
    - 22 -
    from her gambling activity to give to him to make the two car
    purchases was "criminally derived."                    This part of his sufficiency
    challenge, therefore, fails as well. See United States v. Richard,
    
    234 F.3d 763
    ,     769    (1st    Cir.    2000)        ("[T]he     government    must
    prove . . . that [the defendant] had general knowledge of the
    subject property's criminal nature . . . .").
    IV.
    Having dispensed with Rivera's challenges to the jury
    instructions and to the sufficiency of the evidence, we now address
    the two remaining challenges that Rivera makes that concern the
    tie between Castrillon's gambling winnings and her fraud.                       Neither
    challenge has merit.
    A.
    Rivera    contends      first       that    his    convictions    must    be
    reversed because of statements that the prosecutor made in his
    closing argument.           In those statements, the prosecutor told the
    jury that it could convict Rivera if the money used to buy the
    vehicles "came from casino winnings and not directly from victims"
    because that money was nevertheless "criminally derived property."
    Rivera contends that these statements amounted to an erroneous
    assertion     that    the     jury    was        legally       required   to   apply     a
    "presumption that all of Castrillon's money was dirty."
    Rivera    concedes       that        he     did    not   object   to      the
    prosecutor's statements at trial.                 Our review, therefore, is for
    - 23 -
    plain error.     United States v. González-Pérez, 
    778 F.3d 3
    , 20 (1st
    Cir. 2015).    We find none.     As we read the record, the prosecutor
    did not argue that a legal presumption of taint applied to all the
    funds that were used to purchase the cars.      The prosecutor merely
    summarized his view of what had been revealed by the circumstantial
    evidence presented at trial about the nature of the funds used to
    make those transactions.9      Moreover, the District Court instructed
    the jury that "the closing arguments are not evidence."       For these
    reasons,   the    prosecutor's    statements   supply   no   basis   for
    sustaining Rivera's challenge.       United States v. Allen, 
    469 F.3d 11
    , 16 (1st Cir. 2006) (noting that even a mischaracterization of
    the defendant's testimony, provided it was "unintentional and
    isolated" and corrected by a cautionary instruction by the district
    court, "did not prejudice the outcome of the case" and therefore
    did not constitute plain error).
    9 To the extent Rivera argues that the prosecutor "misstated
    Castrillon's testimony," we reject that challenge as well.      As
    Rivera correctly notes, "Castrillon testified that her gambling
    money came from either gambling winnings or loans."      Thus, the
    prosecutor did not err in suggesting to the jury that even if the
    money Rivera used to obtain the two manager's checks used to
    purchase the BMW "came from casino winnings and not directly from
    victims," it was nevertheless "criminally derived property because
    the money she was playing with was the victims' money."
    Significantly, the government never stated that the funds in
    question were "proceeds."
    - 24 -
    B.
    Rivera    also    argues     that    his     convictions      must    be
    overturned because the District Court did not permit his attorney
    to adduce evidence quantifying Castrillon's gambling winnings.
    Rivera did preserve this challenge, and so our review is for abuse
    of discretion.       United States v. DeCologero, 
    530 F.3d 36
    , 58 (1st
    Cir. 2008).
    The record does not show that the District Court barred
    Rivera from presenting this evidence.                   Rather, after Rivera's
    attorney, on re-direct, withdrew a question in which he sought to
    quantify   Castrillon's        gambling       winnings,    the     District   Court
    emphasized    that    Rivera's    attorney       could    pursue    this   line    of
    questioning if he could "show the relevance and accuracy of that
    information."
    Moreover, the additional evidence at issue could not
    have helped Rivera identify a plausible untainted source for the
    funds used to buy the cars.          Much evidence was adduced at trial
    about the size of Castrillon's fraud and her lack of independent
    sources of income.        In fact, during his direct examination of
    Castrillon,    Rivera's       attorney    withdrew       without    objection     his
    question about "[h]ow much money [Castrillon] would win" while
    gambling when the District Court told him that such testimony was
    needlessly cumulative.         Thus, there was no abuse of discretion by
    the District Court.
    - 25 -
    V.
    We now take up Rivera's three remaining challenges. None
    supports the reversal of his convictions.
    A.
    Rivera     first     contends        that   the   prosecutor     acted
    improperly     by   asking    Castrillon        "whether     four   other   trial
    witnesses were lying." Because Rivera did not raise this challenge
    below, our review is for plain error.
    The government does not dispute that the prosecutor's
    error in this regard was clear and obvious.                See United States v.
    Thiongo, 
    344 F.3d 55
    , 61 (1st Cir. 2003) (noting that "it is
    improper for an attorney to ask a witness whether another witness
    lied on the stand").            In order "to constitute plain error,"
    however, the prosecutor's improper questions "must potentially
    have affected the outcome of the district court proceedings."
    United States v. Fernandez, 
    145 F.3d 59
    , 63 (1st Cir. 1998)
    (quoting United States v. Olano, 
    507 U.S. 725
    , 734 (1993)).                   We
    see no basis for concluding that they did.
    Rivera first points to the government's question about
    whether the "salesperson" who testified that Rivera was present
    when the Toyota Sequoia was purchased "was lying."                  But the jury
    heard   testimony    --   and    was    presented      extensive    accompanying
    documentary evidence -- that Rivera purchased the Toyota Sequoia
    on Castrillon's behalf.         We thus do not see how the comment by the
    - 26 -
    prosecutor that is at issue -- even if improper -- was sufficiently
    prejudicial to warrant overturning the verdict.                   See 
    id. at 65
    ("Given    the    strength      of   the   government's   case,    it   stretches
    credulity to believe that the improper framing of these un-
    objected-to questions affected the outcome of the trial.").
    Rivera also fails to show the requisite prejudice from
    the   three      other    instances     that   he   identifies    in    which   the
    prosecutor asked Castrillon whether other witnesses were lying.10
    The   government         put   forth   considerable    evidence    of    Rivera's
    participation in the two vehicle purchases, his closeness to
    Castrillon and, as Rivera himself concedes, his knowledge of and
    participation in the fraud scheme itself.              Thus, "[w]e see no way
    that these few miscast questions could have so tainted the trial
    as to affect its outcome."             
    Id. at 64;
    see also United States v.
    Pereira, __ F.3d __, 
    2017 WL 462104
    , at *12-*13 (1st Cir. Feb. 3,
    2017) (noting a lack of prejudice to the defendant, and thus no
    plain error, where the questions "were limited in number and scope,
    and only pertained to tangential, corroborated testimony").
    10Those three instances are the following.     At one point
    during the government's cross-examination of Castrillon, the
    prosecutor took issue with statements suggesting Rivera was not
    involved in alerting her to the apparent distress of two victims
    of the fraud scheme, Fidel Lozada Gutierrez and Edgardo Vidal. At
    another, the prosecutor disputed Castrillon's account of how
    Rivera learned that a different victim of Castrillon's scheme,
    William Sanchez, had loaned her money.     At a third point, the
    prosecutor challenged Castrillon's testimony concerning how much
    money yet another victim, Roberto Ortiz, had loaned Castrillon.
    - 27 -
    B.
    Rivera next argues that the District Court erred in
    granting the government's motion in limine to exclude evidence
    that   concerned   the    negligence     or    lack   of   due   diligence   of
    Castrillon's victims.       Rivera contends that the District Court's
    ruling limited his ability "to demonstrate just how successful
    Castrillon was in duping people, thereby making it more likely
    that Rivera himself was duped."               Our review is for abuse of
    discretion.    
    DeCologero, 530 F.3d at 58
    .
    As the government correctly points out, the District
    Court permitted Rivera to argue to the jury that he was a victim
    of Castrillon's manipulation and to present evidence in support of
    that argument.     Thus, we do not see how the District Court erred.
    It merely excluded evidence that would have been at best cumulative
    (and, at worst inconsistent with) a side point that Rivera wished
    to make but that was not even in dispute: that Castrillon was a
    skilled fraudster.       Thus, there was no abuse of discretion.
    C.
    Finally, we reject Rivera's claim of cumulative error.
    The record contains strong evidence that the gambling winnings
    Rivera used to buy the cars were, at the least, "derived from" the
    "proceeds" of Castrillon's fraud.        The errors that Rivera alleges,
    however, are not responsible for the jury having heard that
    evidence.     We thus conclude that the errors Rivera points to, if
    - 28 -
    any there were, "in the aggregate, do not come close to achieving
    the critical mass necessary to cast a shadow upon the integrity of
    the verdict."   United States v. Sepulveda, 
    15 F.3d 1161
    , 1196 (1st
    Cir. 1993).
    VI.
    For these reasons, we affirm Rivera's convictions.
    - 29 -