United States v. Martinez-Maldonado , 722 F.3d 1 ( 2013 )


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  •           United States Court of Appeals
    For the First Circuit
    Nos. 12-1289, 12-1290
    UNITED STATES OF AMERICA,
    Appellee,
    v.
    JUAN BRAVO FERNANDEZ; HECTOR MARTÍNEZ MALDONADO,
    Defendants, Appellants.
    APPEALS FROM THE UNITED STATES DISTRICT COURT
    FOR THE DISTRICT OF PUERTO RICO
    [Hon. Francisco A. Besosa, U.S. District Judge]
    Before
    Howard, Lipez, and Thompson,
    Circuit Judges.
    Martin G. Weinberg, with whom David Z. Chesnoff, Chesnoff &
    Schonfeld, Kimberly Homan, Jose A. Pagan, and Pagan Law Offices
    were on brief, for appellant Bravo Fernandez.
    Abbe David Lowell, with whom Christopher D. Man and Chadbourne
    & Parke LLP were on brief, for appellant Martínez Maldonado.
    Peter M. Koski, Deputy Chief, Criminal Division, Public
    Integrity Section, United States Department of Justice, with whom
    Lanny A. Breuer, Assistant Attorney General, and Mary Patrice
    Brown, Deputy Assistant Attorney General, were on brief, for
    appellee.
    June 26, 2013
    LIPEZ, Circuit Judge. This case presents multiple issues
    of substantial importance, including a question of first impression
    in this circuit on the interpretation of the federal program
    bribery statute, 18 U.S.C. § 666.               Defendants are a Puerto Rico
    legislator and a Commonwealth businessman who were charged, inter
    alia, with unlawfully exchanging a trip to Las Vegas to attend a
    prize fight for favorable action on legislation.              A jury returned
    guilty verdicts against both men, Juan Bravo Fernandez ("Bravo")
    and Hector Martínez Maldonado ("Martínez"), and they now challenge
    their     convictions     on   numerous       grounds.    Foremost    is   their
    contention that the jury was allowed to convict on a gratuity
    theory which is beyond the scope of § 666.
    Unlike most circuits to have addressed this issue, we
    conclude that § 666 does not criminalize gratuities.                Because the
    district court's instructions permitted the jury to find guilt on
    the   §    666   counts    based   on     a    gratuity   theory,    Defendants'
    convictions on that count must be vacated.                   In addition, we
    conclude that the Double Jeopardy Clause, though for reasons that
    differ for each Defendant, entitles both men to acquittal on their
    respective conspiracy charges.
    I.
    A. Factual Background
    We briefly summarize the relevant facts, reserving for
    our analysis a more detailed discussion of the facts relevant to
    -3-
    each issue presented on appeal.              We view the facts in the light
    most favorable to the jury's verdicts.                   See United States v.
    Ciresi, 
    697 F.3d 19
    , 23 (1st Cir. 2012).
    From January 2005 until early 2011, Martínez served in
    the Senate of the Commonwealth of Puerto Rico.1                   When Martínez
    became a senator he was assigned to the Public Safety Committee,
    where he served as chairman.            Bravo was the president of Ranger
    American, a private firm that provides security services, including
    armored car transportation and security guard staffing.
    In   early   2005,   Bravo   advocated    for   the   passage    of
    legislation related to the security industry in Puerto Rico.                    One
    of these bills, Senate Project 410, addressed issues pertaining to
    security at shopping malls, while the other, Senate Project 471,
    involved licensing requirements for armored car companies.                      The
    government produced testimony at trial that the passage of these
    bills would have provided substantial financial benefits to Ranger
    American. As chairman of the Public Safety Committee, Martínez was
    in   a       position   to   exercise   a    measure   of   control    over     the
    introduction and progression of the bills through the Committee and
    the Senate.
    1
    The record does not specify the duration of Martínez's
    tenure in the Puerto Rico Senate. We take judicial notice of the
    fact that he resigned his seat in early 2011. See Fed. R. Evid.
    201(b) (allowing a court to take judicial notice of a fact "not
    subject to reasonable dispute because it . . . can be accurately
    and readily determined from sources whose accuracy cannot
    reasonably be questioned").
    -4-
    On May 14, 2005, prominent Puerto Rican boxer Félix
    "Tito" Trinidad was scheduled to fight Ronald Lamont "Winky" Wright
    at the MGM Grand Hotel & Casino in Las Vegas, Nevada.    On March 2,
    Bravo purchased four tickets to the fight at a cost of $1,000 per
    ticket.    The same day, Martínez submitted Senate Project 410 for
    consideration by the Puerto Rico Senate.      On April 20, Martínez
    presided over a Public Safety Committee hearing on Senate Project
    471 at which Bravo testified.    The next day, Bravo booked one room
    at the Mandalay Bay Hotel in Las Vegas.    On May 11, Martínez issued
    a Committee report in support of Senate Project 471.
    Bravo arranged for first-class airline tickets to Las
    Vegas for himself, Martínez, and another senator, Jorge de Castro
    Font.2    In Las Vegas, the three men stayed in separate rooms at the
    Mandalay Bay for two nights.     Bravo paid for Martínez's room the
    first night, and de Castro Font paid for Martínez's room the second
    night. The men, along with de Castro Font's assistant, went out to
    dinner the day before the fight, with Bravo footing the $495 bill.
    The men attended the Tito Trinidad fight the next night, using the
    $1,000 tickets Bravo had purchased.
    2
    In 2008, Jorge de Castro Font was indicted on numerous
    counts relating to corruption by an elected official. See United
    States v. De Castro-Font, 
    587 F. Supp. 2d 353
    , 355 (D.P.R. 2008).
    On January 29, 2009, de Castro Font pled guilty to 21 counts of the
    indictment filed against him.    He received a sentence of sixty
    months' imprisonment. See United States v. De Castro-Font, 08-CR-
    337-01(FAB), Doc. 353 (D.P.R. May 17, 2011).
    -5-
    The day after the fight, Bravo, Martínez, and de Castro
    Font flew from Las Vegas to Miami, where they spent the night in
    individual hotel rooms at the Marriott South Beach. The rooms were
    reserved and paid for by Bravo at a total cost of $954.75.      The
    next day, on May 16, the three returned to Puerto Rico.
    On May 17, de Castro Font, acting as Chair of the
    Committee on Rules and Calendars, scheduled an immediate vote on
    the floor of the Puerto Rico Senate for Senate Project 471.    Both
    de Castro Font and Martínez voted in support of the bill.   The next
    day, Martínez issued a Committee report in favor of Senate Project
    410.   On May 23, de Castro Font scheduled an immediate vote on the
    floor of the Senate for Senate Project 410.   Again, both de Castro
    Font and Martínez voted for the bill.
    B. Procedural Background
    On June 22, 2010, a grand jury returned an indictment
    charging Bravo and Martínez with (1) violating 18 U.S.C. § 371 by
    conspiring to (a) commit federal program bribery, and (b) travel in
    interstate commerce in aid of racketeering; (2) violating 18 U.S.C.
    § 1952(a)(3)(A) by traveling in interstate commerce with the intent
    to "[p]romote, establish, carry on, and facilitate the promotion,
    establishment, and carrying on," of unlawful activity, specifically
    (a) federal program bribery in violation of § 666, and (b) bribery
    in violation of P.R. Laws Ann., tit. 33, §§ 4360 and 4363; and (3)
    federal program bribery in violation of § 666.        Martínez was
    -6-
    additionally indicted for obstruction of justice, in violation of
    18 U.S.C. § 1512(b)(3).
    The case went to trial on February 14, 2011. On March 7,
    2011, a jury convicted Bravo of conspiracy to travel in interstate
    commerce in aid of racketeering (count one), interstate travel in
    aid of racketeering with the intent to promote bribery in violation
    of Puerto Rico law (count two), and federal program bribery (count
    four).       The jury found Martínez guilty of conspiracy (count one),
    but checked "No" as to each potential object of the conspiracy. He
    was also convicted of federal program bribery (count five).                   The
    jury acquitted Martínez of interstate travel in aid of racketeering
    (count three) and obstruction of justice (count six).
    The trial court granted Bravo's motion for judgment of
    acquittal on count two, finding that the repeal of the Puerto Rico
    bribery laws before the trip took place made it impossible for
    Bravo       to   satisfy   the   "thereafter"   element3   of   a    Travel   Act
    violation. It initially "dismissed" Martínez's conviction on count
    one because the jury rejected both potential objects of the
    conspiracy, but then "reinstated" the conviction the next day, and
    eventually dismissed it without prejudice.            On March 1, 2012, the
    district         court   sentenced   both    defendants    to   48   months    of
    3
    See infra Part V.
    -7-
    imprisonment.     Bravo received a fine of $175,000 and Martínez a
    fine of $17,500.4
    C. Issues on Appeal
    Both   Defendants    challenge    their   substantive    §    666
    convictions on numerous grounds.         Martínez challenges on double
    jeopardy grounds the district court's decision to reinstate his
    conspiracy conviction and then dismiss it without prejudice. Bravo
    also challenges his conspiracy conviction, arguing, among other
    things, that the judgment of acquittal on the Travel Act count
    requires the entry of judgment of acquittal on the conspiracy
    count, as § 666, given the findings by the jury, cannot serve as an
    object of the conspiracy to violate the Travel Act.
    II.
    Defendants raise several challenges to the scope of the
    federal program bribery statute, 18 U.S.C. § 666, and, identifying
    certain   elements   of   the   statute,    they   also   claim   that   the
    circumstances of this case do not satisfy any of those elements.
    We review the questions of law raised in their arguments de novo,
    4
    Bravo and Martínez both filed motions for bail pending
    appeal before the district court, and both motions were denied.
    Martínez began serving his sentence on March 1, 2012, while Bravo
    began serving his on May 7, 2012. Bravo began serving his sentence
    later because of some health issues.      Defendants subsequently
    brought their motions for bail pending appeal before us, and, in
    early March 2012, both were denied. Following oral argument in
    November 2013, we received Defendants' renewed motions for bail
    pending appeal on December 11, 2012. They were granted on January
    2, 2013.
    -8-
    United States v. Place, 
    693 F.3d 219
    , 227 (1st Cir. 2012); to the
    extent    that    their    claims   challenge      the    sufficiency      of    the
    government's evidence, we again employ de novo review, appraising
    the proof in the light most favorable to the verdict, United States
    v. Rodríguez-Vélez, 
    597 F.3d 32
    , 38 (1st Cir. 2010).
    A. Agents
    Section 666 requires the government to show that the
    individual receiving or soliciting the bribe was "an agent of an
    organization, or of a State, local, or Indian tribal government, or
    any agency thereof."        18 U.S.C. § 666(a)(1).         The term "agent" is
    defined as "a person authorized to act on behalf of another person
    or a government and, in the case of an organization or government,
    includes a servant or employee, and a partner, director, officer,
    manager, and representative." 
    Id. § 666(d)(1). Defendant
    Martínez
    maintains that he could not be convicted under § 666(a)(1)(B)
    because he was not an agent of the Commonwealth of Puerto Rico.
    Defendant Bravo argues that because neither Martínez nor de Castro
    Font were agents of the Commonwealth, he cannot be guilty of
    bribing them pursuant to § 666(a)(2).
    1. The Scope of the Agency
    At    the     outset,   we    reject   any     notion   that        state
    legislators are categorically exempt from prosecution under § 666.
    Indeed,     the    plain     language      of   the      statute    includes       a
    "representative" of a "government" in the list of positions that
    -9-
    fall under the statute's definition of "agent," 18 U.S.C. §
    666(d)(1), and there is no more classic government "representative"
    than a legislative branch officer.      See United States v. Lipscomb,
    
    299 F.3d 303
    , 333 (5th Cir. 2002) ("Congress clearly sought to
    apply § 666 to legislative-branch officials."); United States v.
    Sunia, 
    643 F. Supp. 2d 51
    , 67 (D.D.C. 2009) (acknowledging that "a
    legislator who misuses his legislative authority to facilitate
    corrupt practices affecting agency programs that receive federal
    funds may well fall within the ambit of § 666").
    Defendants' more nuanced argument is that the government
    failed to sufficiently specify the entity for which Martínez and de
    Castro Font were agents.   They maintain that Martínez may only be
    appropriately classified as a representative (and thus an agent) of
    the Puerto Rico Senate, and not -- as the indictment alleged -- of
    the Commonwealth as a whole.      This distinction is significant,
    Defendants claim, because the Puerto Rico Senate itself had no
    connection with, or control over, the federal funds identified by
    the two government witnesses, and without such a connection the
    government cannot show that "the organization, government, or
    agency receives, in any one year period, benefits in excess of
    $10,000 under a Federal program."        18 U.S.C. § 666(b).      If the
    $10,000 threshold is not met, then the actions of the agents of the
    non-qualifying   organization,   government,   or   agency   --   or   the
    -10-
    actions of others with respect to those agents -- cannot implicate
    § 666.
    Once again we need go no further than the plain language
    of the statute to conclude that Martínez and de Castro Font may be
    properly considered "agents" of the Commonwealth of Puerto Rico.
    Among the five types of entities for which one may be an agent
    within the meaning of § 666 is a state government.5           See 18 U.S.C.
    § 666(a)(1), (2) (referring to "an agent of an organization, or of
    a   State,   local,   or    Indian   tribal   government,   or   any    agency
    thereof").       The Puerto Rico Senate is a constituent part of the
    Commonwealth government, created by the Puerto Rico Constitution.
    See P.R. Const. art. III, § 1.         Its members are thus part of the
    limited category of government officials who represent the "State"
    as a whole, unlike employees of localities or of agencies at every
    level of government.       As such, they easily fall within the concept
    of "an agent of . . . a State . . . government."            Martínez and de
    Castro    Font     were    thus   properly    considered    agents     of   the
    Commonwealth of Puerto Rico under § 666.
    At trial, the Associate Director for the Office of Budget
    and Management testified that during 2005 -- the year of the
    5
    Under § 666, the definition of "State" includes "a State of
    the United States, the District of Columbia, and any commonwealth,
    territory, or possession of the United States."         18 U.S.C.
    § 666(d)(4) (emphasis added). Because "State" is a term of art in
    § 666, we shall refer to Martínez and de Castro Font as "State
    senators."
    -11-
    charged conduct -- the Commonwealth received over $4.7 billion in
    federal funds.     Because Martínez and de Castro Font are agents of
    the Commonwealth, the evidence was sufficient to show that they are
    agents of a "government . . . [that] receives, in any one year
    period, benefits in excess of $10,000 under a Federal program." 18
    U.S.C. § 666(b).
    2. Agent Control of Expenditures
    Defendants argue that being an "agent" under § 666 must
    include an element beyond merely representing the entity.           Framing
    their argument partially in constitutional terms, they assert that,
    to   establish    the   requisite   link    to   Congress's   authority    to
    legislate under the Necessary and Proper Clause, an "agent" under
    § 666 "must be 'authorized to act on behalf of [the entity] with
    respect to its funds.'"     United States v. Whitfield, 
    590 F.3d 325
    ,
    344 (5th Cir. 2009) (quoting United States v. Phillips, 
    219 F.3d 404
    , 411 (5th Cir. 2000)); see also Sabri v. United States, 
    541 U.S. 600
    , 605 (2004) (describing Congress's authority under the
    Necessary   and   Proper   Clause).        Defendants   maintain   that   the
    government failed to adduce any evidence at trial establishing that
    either Martínez or de Castro Font, acting as senators, had the
    authority to control the expenditure of funds by any entity
    receiving federal funds, and that the senators therefore do not
    qualify as "agents" for purposes of § 666.
    -12-
    We    disagree.     Neither    the   statutory    language   nor
    constitutional principles lead to such a restricted understanding
    of the provision.     As the Eleventh Circuit recently noted when
    presented with this argument, "[n]owhere does the statutory text
    either mention or imply an additional qualifying requirement that
    the person be authorized to act specifically with respect to the
    entity's funds." United States v. Keen, 
    676 F.3d 981
    , 989-90 (11th
    Cir. 2012).     The statute merely requires that the individual be
    "authorized to act on behalf of another person or government."          18
    U.S.C. § 666(d)(1).    In interpreting the text of a statute, "we
    will not depart from, or otherwise embellish, the language of a
    statute absent either undeniable textual ambiguity, or some other
    extraordinary consideration, such as the prospect of yielding a
    patently absurd result."    Pritzker v. Yari, 
    42 F.3d 53
    , 67-68 (1st
    Cir. 1994) (citations omitted); cf. Salinas v. United States, 
    522 U.S. 52
    , 57-58 (1997).      Defendants fail to show that any absurd
    result would follow from a reading loyal to the plain meaning of
    the statute.
    The    Supreme    Court's     and    this    circuit's   §   666
    jurisprudence support the conclusion that the statute incorporates
    no embellishment on the concept of "agent."           Indeed, the Supreme
    Court has repeatedly rejected constructions of § 666 that would
    impose limits beyond those set out in the plain meaning of the
    statute. In Salinas, for example, the Court rejected a defendant's
    -13-
    attempt to read into the statute an extra-textual requirement of
    proof that "the bribe in some way affected federal funds, for
    instance by diverting or misappropriating them, before the bribe
    violates § 
    666(a)(1)(B)." 522 U.S. at 55-56
    .         In reaching its
    conclusion,    the   Court    pointed   to   the   "enactment's     expansive,
    unqualified language, both as to the bribes forbidden and the
    entities covered."      
    Id. at 56. Seven
    years later, in Sabri v.
    United States, the Court rejected a similar argument that the
    statute requires proof of a "nexus" between a bribe or kickback and
    some federal money.          It noted that while "not every bribe or
    kickback offered or paid to agents of governments covered by
    § 666(b) will be traceably skimmed from specific federal payments,
    or show up in the guise of a quid pro quo for some dereliction in
    spending a federal grant," the absence of such links does not
    "portend[] . . . enforcement beyond the scope of federal interest,
    for the reason that corruption does not have to be that limited to
    affect the federal 
    interest." 541 U.S. at 605-06
    ; see also Fischer
    v. United States, 
    529 U.S. 667
    , 677-79 (2000) (adopting broad
    reading of "benefits" under § 666(b) in light of statutory language
    "reveal[ing] Congress' expansive, unambiguous intent to ensure the
    integrity of organizations participating in federal assistance
    programs").
    We   previously      addressed     the   scope   of   §   666(d)(1)'s
    definition of "agent" in United States v. Sotomayor-Vázquez, 249
    -14-
    F.3d 1 (1st Cir. 2001).     Drawing largely from the Supreme Court's
    interpretation   of   the   statute   in   Salinas,   we   held   that   "an
    expansive definition of 'agent' is necessary to fulfill the purpose
    of § 666, i.e., to protect the integrity of federal funds."         
    Id. at 8. In
    support of this reading, we quoted at length from the
    dissent in United States v. Phillips:
    [T]he expansive statutory definition [in
    § 666(d)(1)] recognizes that an individual can
    affect agency funds despite a lack of power to
    authorize    their     direct    disbursement.
    Therefore, to broadly protect the integrity of
    federal funds given to an agency, § 666
    applies to any individual who represents the
    agency in any way, as representing or acting
    on behalf of an agency can affect its funds
    even if the action does not directly involve
    financial disbursement.
    
    Id. at 8 (quoting
    Phillips, 219 F.3d at 422 
    n.3 (Garza, J.,
    dissenting)).    We thus held that "an outside consultant with
    significant managerial responsibility" could be an "agent" of a
    government entity.    
    Id. In keeping with
    our own precedent and that of the Supreme
    Court, we conclude that embracing an approach faithful to the plain
    language of § 666 is appropriate here.          Even if the officials
    accepting bribes do not have the ability to control the expenditure
    of an entity's funds, "it cannot be denied that their fraudulent
    conduct poses a threat to the integrity of the entity, which in
    turn poses a threat to the federal funds entrusted to that entity."
    
    Keen, 676 F.3d at 990
    ; see also United States v. Hines, 541 F.3d
    -15-
    833, 835-36 (8th Cir. 2008).              Such conduct "raise[s] the risk
    [that]    participating       organizations     will   lack     the     resources
    requisite to provide the level and quality of care envisioned by
    the program."     
    Fischer, 529 U.S. at 681-82
    ; cf. 
    Sabri, 541 U.S. at 606
      ("Money   is    fungible,    bribed     officials   are    untrustworthy
    stewards of federal funds, and corrupt contractors do not deliver
    dollar-for-dollar value.").         Narrowing the scope of § 666(d)(1)'s
    definition of "agent" would be "inconsistent not only with the
    expansive, unqualified language that Congress has elected to use,
    but also with Congress' clear objective of ensuring the integrity
    of entities receiving substantial sums of federal funds."                     
    Keen, 676 F.3d at 991
    (citation omitted) (internal quotation marks
    omitted).   We therefore decline to do so.
    These     concerns    about    financial   integrity       also    doom
    Defendants' constitutional argument. "[I]n determining whether the
    Necessary   and      Proper   Clause   grants    Congress     the     legislative
    authority to enact a particular federal statute, we look to see
    whether the statute constitutes a means that is rationally related
    to the implementation of a constitutionally enumerated power."
    United States v. Comstock, 
    130 S. Ct. 1949
    , 1956 (2010).                        In
    rejecting a different Necessary and Proper Clause challenge to
    § 666 in Sabri,6 the Supreme Court wrote:
    6
    The defendant in Sabri argued that § 666 could not be
    constitutionally applied "because it fails to require proof of any
    connection between a bribe or kickback and some federal money."
    -16-
    Congress has authority under the Spending
    Clause to appropriate federal moneys to
    promote the general welfare, Art. I, § 8, cl.
    1, and it has corresponding authority under
    the Necessary and Proper Clause . . . to see
    to it that taxpayer dollars appropriated under
    that power are in fact spent for the general
    welfare, and not frittered away in graft or on
    projects undermined when funds are siphoned
    off or corrupt public officers are derelict
    about demanding value for 
    dollars. 541 U.S. at 605
    .
    We have no hesitation in concluding that "measures to
    police the integrity of entities receiving federal funds fall under
    the scope of this power," 
    Keen, 676 F.3d at 991
    , even absent
    evidence of an agent's authority to act specifically with respect
    to the covered entity's funds.    "Congress does not have to sit by
    and accept the risk of operations thwarted by local and state
    improbity."   
    Sabri, 541 U.S. at 605
    .   To accept that there can only
    be harmful effects of such dishonest conduct when the actor has
    authority to control the expenditure of the entity's funds would be
    naive; to accept that the prohibition of such conduct by such
    individuals is not "rationally related" to Congress' implementation
    of its constitutionally enumerated powers would be an unduly
    restrictive application of that standard.      The Supreme Court has
    stated that to fall within the scope of the federal interest, "[i]t
    is certainly enough that the statutes condition the offense on a
    threshold amount of federal dollars defining the federal 
    interest, 541 U.S. at 604
    .
    -17-
    such as that provided [in § 666]."            
    Id. at 606. We
    see no basis
    for departing from that view here.
    B. The Transactional Element
    For a bribe to fall within the purview of § 666, it must
    be made "in connection with any business, transaction, or series of
    transactions of [the covered] organization, government, or agency
    involving   anything   of   value     of    $5,000    or   more."     18     U.S.C.
    § 666(a)(1)(B), (a)(2).      This requirement has been referred to as
    the "transactional element" of § 666.              United States v. Robinson,
    
    663 F.3d 265
    , 270 (7th Cir. 2011).             Defendants point out that a
    circuit   split   exists    as   to   how    the   $5,000   threshold      in    the
    transactional element is met, but argue that under either approach
    the   government's     evidence       was    insufficient.          Taking      this
    opportunity to clarify the correct standard, we conclude that under
    the proper approach the evidence was sufficient to satisfy the
    $5,000 threshold and the transactional element generally.
    1. Value of Bribe or Transaction?
    In determining how to calculate the $5,000 requirement,
    some courts have suggested that a court should look to the value of
    the bribe actually offered or paid.            See United States v. Abbey,
    
    560 F.3d 513
    , 521 (6th Cir. 2009) (stating that "§ 666 contains
    . . . a requirement that the illegal gift or bribe be worth over
    $5,000"); United States v. Spano, 
    401 F.3d 837
    , 839 (7th Cir. 2005)
    ("[T]o establish a case under § 666, the government need only prove
    -18-
    that an agent . . . was offered or accepted a bribe worth $5000 or
    more . . . ."); United States v. LaHue, 
    170 F.3d 1026
    , 1028 (10th
    Cir. 1999) (stating that § 666 "prohibits the unlawful acceptance
    of anything of value of $5,000 or more").         Other courts, however,
    have held that the $5,000 requirement "refers to the value of the
    'business, transaction, or series of transactions,' not the value
    of the bribe."    United States v. McNair, 
    605 F.3d 1152
    , 1185 n.38
    (11th Cir. 2010); see also United States v. Duvall, 
    846 F.2d 966
    ,
    976 (5th Cir. 1988) ("[I]t is clear that the $5000 figure qualifies
    the transactions or series of transactions that the recipient of
    the bribe carries out in exchange for receiving 'anything of
    value.'").
    In our view, the statutory language is unambiguous and
    plainly requires the latter reading.        Applied to the present case,
    § 666(a)(1)(B) prohibits a government agent from accepting or
    agreeing to accept "anything of value" from another individual
    "intending to be influenced or rewarded in connection with any
    business,     transaction,   or   series    of   transactions"   of   that
    government "involving anything of value of $5,000 or more."            18
    U.S.C.   §   666(a)(1)(B)    (emphasis     added).    Section    666(a)(2)
    prohibits offering, giving, or agreeing to give "anything of value"
    to an individual with the "intent to influence or reward" a
    government agent "in connection with any business, transaction, or
    series of transactions" of that government "involving anything of
    -19-
    value of $5,000 or more."        
    Id. § 666(a)(2) (emphasis
    added).         The
    thing accepted or agreed to be accepted in § 666(a)(1)(B) -- and
    the thing given or offered in § 666(a)(2) -- is the bribe.               Thus,
    the bribe can be "anything of value" -- it need not be worth
    $5,000.    The $5,000 element instead refers to the value of the
    "business" or "transaction" sought to be influenced by the bribe.
    "In other words, the subject matter of the bribe must be valued at
    $5,000 or more; the bribe itself need only be 'anything of value.'"
    
    Robinson, 663 F.3d at 271
    .
    We note, however, that the value of the bribe may be
    relevant in determining the value of the bribe's objective.                 In
    United States v. Marmolejo, 
    89 F.3d 1185
    (5th Cir. 1996), for
    example, the court looked to the value of bribes where the subject
    matter    of    the   bribes   consisted    of   "intangible   items."     The
    defendants in Marmolejo were two local law enforcement officers who
    had agreed to permit conjugal visits between an inmate and his wife
    (and his girlfriend) in exchange for a monthly payment of $6,000
    and $1,000 per conjugal visit.        
    Id. at 1191. The
    court noted that
    "[t]he transactions involved something of value -- conjugal visits
    that [the prisoner] was willing to pay for," 
    id. at 1193 --
    and it
    looked to "traditional valuation methods" to estimate that value,
    
    id. at 1194. The
    court concluded that the prisoner's willingness
    to pay $6,000 per month plus $1,000 per visit set the market value
    for the conjugal visits, and it thus found that the transactions
    -20-
    between the prisoner and the two defendants "involved something of
    value of $5,000 or more."     
    Id. at 1194 (internal
    quotation marks
    omitted).
    Hence, where the subject matter of the bribe is a "thing
    of value" without a fixed price, courts may look to the value of
    the bribe as evidence of the value of the "business, transaction,
    or series of transactions." That collateral use does not alter the
    proposition that the bribe itself need only consist of "anything of
    value."
    2. "Business or transaction" requirement
    Defendants maintain that the enactment of Senate Projects
    410 and 471 should not be considered to be "in connection with any
    business, transaction, or series of transactions . . . involving
    anything of value of $5,000 or more" under § 666.         They offer
    several justifications for this position.      We find none of them
    persuasive.
    First, Defendants focus on the "in connection with"
    language. Their attack is anchored in a Fifth Circuit case, United
    States v. Whitfield, which involved two state judges who were
    convicted of accepting bribes from an attorney in exchange for
    favorable rulings in his 
    cases. 590 F.3d at 335
    .    The government
    argued, and the court assumed, that the judges were "agents" of the
    Administrative Office of the Courts ("AOC"), a Mississippi state
    agency that received over $10,000 in federal funds and was "charged
    -21-
    with assist[ing] in the efficient administration of the nonjudicial
    business of the courts of the state."                      
    Id. at 344 (emphasis
    added)
    (citation omitted) (internal quotation marks omitted).                            The court
    held,    however,         that   the    judges'       rulings     were      not    made    "in
    connection with" the business or transactions of the AOC, as they
    were made while the judges were performing purely judicial duties.
    
    Id. at 346-47. Here,
    Defendants maintain that the federal funds
    identified by the government went to the Puerto Rico Departments of
    Education and Treasury, and because there is no nexus between the
    Departments of Education and Treasury and the act of legislating
    Senate    Projects        410    and    471   in     the    Puerto    Rico    Senate,     the
    legislation         was    not    "in    connection          with"    the    business      or
    transactions of the federally funded entity.
    Whatever the merits of Whitfield's "nexus" requirement,
    they are not implicated in this case, as we have determined that
    Martínez and de Castro Font were agents of the Commonwealth of
    Puerto Rico, which receives federal funds.                           When the judges in
    Whitfield were acting in their capacity as judicial decisionmakers,
    they were not acting within their scope as agents of the AOC, as
    the AOC was specifically limited to the nonjudicial business of the
    courts.    By contrast, when Martínez and de Castro Font were acting
    in their capacity as legislators, they were performing the precise
    functions that members of a state legislative body perform as
    agents    of    a    state       government.          The     legislative         acts    that
    -22-
    constituted the subject of the bribes had a direct "connection with
    the business, transaction, or series of transactions" of the
    Commonwealth of Puerto Rico.
    Second, Defendants argue that the passing of Senate
    legislation cannot be considered "business" or a "transaction"
    under § 666.        The thrust of their argument is that the terms
    "business"    and   "transaction"   should    be   construed   narrowly   to
    encompass only commercial conduct, and "the Senate does not conduct
    business or financial transactions through legislating."
    In Salinas, the Supreme Court rejected a defendant's
    similar attempt to impose a narrowing construction on § 
    666. 522 U.S. at 57
    . There, the defendant argued that federal funds must be
    affected to violate § 666(a)(1)(B).          
    Id. at 56. Looking
    to the
    language of the statute, the Court concluded that the word "any,"
    which precedes the business or transaction clause, undercuts the
    attempt to impose the defendant's narrow interpretation.            
    Id. at 56-57. The
       Court's   emphasis   on     the   expansive   language   in
    § 666(a)(1)(B) in Salinas suggests that the courts should avoid
    imposing narrowing constructions on that language.             Furthermore,
    such a reading would foreclose large swaths of government activity
    that, though technically "non-commercial," could be profitable for
    unscrupulous individuals to attempt to influence.              This narrow
    construction would be contrary to Congress's intent. See 
    id. at 56 (citing
    § 666's "expansive, unqualified language, both as to the
    -23-
    bribes   forbidden   and    the   entities    covered,"   as     evidence   of
    legislative   intent   to    construe      statute   broadly).      Recently
    confronting this argument, the Seventh Circuit stated:
    The   "business"   of   a   federally   funded
    "organization, government, or agency" is not
    commonly "business" in the commercial sense of
    the word.    An interpretation that narrowly
    limits the scope of the transactional element
    to   business   or   transactions   that   are
    commercial in nature would have the effect of
    excluding bribes paid to influence agents of
    state and local governments. This contradicts
    the express statutory text.
    
    Robinson, 663 F.3d at 274
    ; see also 
    Marmolejo, 89 F.3d at 1191-92
    .
    We agree, and hold that the business or transaction clause in § 666
    does not limit the statute's reach to purely commercial conduct.
    Third, Defendants focus on the word "involving,"7 and
    posit that in order to satisfy § 666, the profit that Ranger
    American would stand to gain from the passage of the Senate
    Projects would "have to have been a part of or a necessary
    consequence of the legislation or have been included in its scope
    to satisfy the $5,000 requirement." Because the legislation itself
    was "revenue-neutral" and gave nothing directly to Ranger American,
    Defendants maintain that neither of the Senate Projects "involved"
    7
    See 18 U.S.C. § 666(a)(1)(B) (prohibiting an agent from,
    inter alia, accepting or agreeing to accept anything of value
    "intending to be influenced or rewarded in connection with any
    business, transaction, or series of transactions of such
    organization, government, or agency involving anything of value of
    $5,000 or more") (emphasis added).
    -24-
    prospective   revenues     for   Ranger      American    (and,   by   extension,
    Bravo).
    We find no support in the case law or the statutory
    language for this unnecessarily restrictive interpretation of
    § 666.    Even if legislation is revenue-neutral on its face, it is
    sufficient if the direct and foreseeable effect of that legislation
    would be to give the individual offering the bribe a particular
    desired    result   --   assuming,    of     course,    that   the    transaction
    involved    something    of   value   of     $5,000    or   more.      Here,   the
    government presented evidence that the foreseeable effect of the
    passage of Senate Project 471 would be a change in the armored car
    service industry, which in turn would result in financial benefits
    to Ranger American and Bravo far exceeding $5,000.               This impact is
    sufficient to satisfy the "involving" requirement of § 666.8
    3. Sufficiency of the Evidence
    With the appropriate understanding of the statute in
    mind, we can easily reject Defendants' sufficiency challenge as to
    the $5,000 requirement.       Miguel Portilla, the president of Capitol
    8
    For the reasons discussed above, we also reject Defendants'
    claim that it would somehow violate the Due Process Clause to apply
    § 666 to state senators who receive bribes in connection with
    legislation pending before them. Such prosecutions fall squarely
    within the plain terms of § 666. See United States v. Councilman,
    
    418 F.3d 67
    , 84-85 (1st Cir. 2005) (rejecting defendant's argument
    that court engaged in "unforeseeably expansive interpretation" of
    criminal statute, as acts alleged constitute "'conduct that . . .
    the statute . . . has fairly disclosed to be within its scope.'"
    (quoting United States v. Lanier, 
    520 U.S. 259
    , 266 (1997))).
    -25-
    Security -- a company with which Ranger American competed --
    testified that Senate Project 471, which sought to amend Law 108,9
    would have forced Ranger American's only competitors in the armored
    car protection business to close down, thereby ensuring that Ranger
    American would have an effective monopoly on that sector of the
    security industry in Puerto Rico.       Nestor Medina, the former
    general manager of Loomis Puerto Rico -- a subsidiary of Loomis
    U.S., an armored car service -- testified that Loomis controlled
    roughly 35% of the armored car service industry, Ranger American
    52%, and Brinks the remainder.     Medina stated that Loomis Puerto
    Rico netted $1.5 million in profits in 2005, and that there would
    therefore be an extra $1.5 million in additional profits available
    for other armored car companies to capture if Loomis were to leave
    the market.10   Because, according to Portilla's testimony, Ranger
    American would have been the only company left in that market, it
    9
    Portilla testified that Law 108 regulates the licensing of
    security agencies in Puerto Rico.
    10
    Defendants take issue with certain of the district court's
    evidentiary rulings as to Medina's testimony. These arguments do
    not affect our sufficiency analysis for two reasons.        First,
    Defendants would have suffered no prejudice by this testimony.
    Portilla's testimony -- which is not challenged by Defendants --
    alone provides sufficient evidence on this issue. Any error with
    respect to the admission of Medina's testimony would therefore be
    harmless.    Second, reviewing the district court's evidentiary
    rulings under the proper standard, see United States v. Appolon,
    
    695 F.3d 44
    , 60 (1st Cir. 2012), we cannot say that the district
    court abused its discretion in permitting Medina to testify on
    redirect about his views regarding Senate Project 471 and its
    potential impact on Loomis, nor in its decision denying recross of
    Medina.
    -26-
    is reasonable to conclude that Bravo's company would stand to
    capture a substantial portion of that profit.                  This testimony
    provided sufficient evidence for a reasonable jury to conclude that
    Senate Project 471 was worth $5,000 or more to Bravo.
    III.
    Defendants      challenge       the    district      court's   jury
    instructions as to the § 666 counts on several grounds.               We need
    reach only Defendants' contention that the court's instructions,
    reinforced by the government's closing argument, permitted the jury
    to find them guilty of offering and receiving a gratuity, rather
    than a bribe. This claim necessarily encompasses the argument that
    § 666 does not in fact criminalize gratuities, a question of first
    impression   in   this   circuit   and    an    issue   that   has   generated
    considerable debate in the courts and among commentators.
    "We review de novo preserved claims of legal error in
    jury instructions, but we review for abuse of discretion claimed
    errors in instructions' form or wording." Uphoff Figueroa v.
    Alejandro, 
    597 F.3d 423
    , 434 (1st Cir. 2010).            In our review, "we
    look to the challenged instructions in relation to the charge as a
    whole, asking whether the charge in its entirety -- and in the
    context of the evidence -- presented the relevant issues to the
    jury fairly and adequately." Drumgold v. Callahan, 
    707 F.3d 28
    , 53
    (1st Cir. 2013) (quoting Sony BMG Music Entm't v. Tenenbaum, 
    660 F.3d 487
    , 503 (1st Cir. 2011)) (internal quotation marks omitted).
    -27-
    Even if we find that a court's instructions were erroneous, we will
    vacate only if we determine that the error was prejudicial "based
    on a review of the record as a whole."      Mass. Eye & Ear Infirmary
    v. QLT Phototherapeutics, Inc., 
    552 F.3d 47
    , 72 (1st Cir. 2009).
    We begin by reviewing the instructions. Because we agree
    that they allowed a gratuities theory of guilt, we then consider
    the scope of § 666.
    A. The Instructions
    1. Background
    Three   of   the   district   court's   thirty-six   jury
    instructions are relevant here.     The first is Jury Instruction 20,
    titled "Bribery Concerning Programs Receiving Federal Funds, 18
    U.S.C. § 666(a)(2)." This instruction concerns Defendant Bravo. It
    explains that
    Defendant Bravo is accused of corruptly
    giving, offering, or agreeing to give things
    of value to defendant Martínez and/or Jorge de
    Castro-Font, with intent to influence or
    reward    defendant    Martínez   and/or    de
    Castro-Font in connection with a business,
    transaction, or series of transactions of the
    Commonwealth   of   Puerto   Rico   government
    involving more than $5,000.
    Much of the language that follows this introduction tracks the
    language of the statute and is not problematic.         For instance,
    paragraphs two through four of Jury Instruction 20 state the
    following:
    For you to find defendant Bravo guilty of
    bribery, you must be convinced that the
    -28-
    Government has proven each of the following
    things beyond a reasonable doubt:
    First, that defendant Bravo gave,
    offered, or agreed to give any thing of value
    to any person;
    Second, that defendant Bravo did so
    corruptly with the intent to influence or
    reward an agent of the Puerto Rico government
    in connection with any business, transaction,
    or series of transactions of the Puerto Rico
    government . . . .
    This same type of statute-tracking language is found in
    the   second   relevant    instruction,       Jury   Instruction    21,   titled
    "Bribery Concerning Programs Receiving Federal Funds, 18 U.S.C.
    § 666(a)(1)(B)."     This instruction concerns the § 666 charges
    against Defendant Martínez.        Paragraphs two through five state:
    For you to find defendant Martínez guilty of
    bribery, you must be convinced that the
    Government has proven each of the following
    things beyond a reasonable doubt:
    First, that defendant Martínez was an
    agent of the Commonwealth of Puerto Rico
    government whose duties included those of an
    elected Senator of the Commonwealth of Puerto
    Rico, as charged;
    Second,    that    defendant    Martínez
    solicited, demanded, accepted or agreed to
    accept any thing of value from another person;
    Third, that defendant Martínez did so
    corruptly with the intent to be influenced or
    rewarded in connection with some business,
    transaction or series of transactions of the
    Puerto Rico government . . . .
    However, certain parts of these two instructions include
    language   that   does    not   track   the    statute.     Among    these   are
    paragraph ten of Jury Instruction 20 and paragraph eleven of Jury
    Instruction 21.    Paragraph ten states:
    -29-
    When considering the First and Second
    elements above, I instruct you that a
    defendant is not required to have given,
    offered, or agreed to give a thing of value
    before the business, transaction, or series of
    transactions.    Rather, the Government may
    prove that defendant Bravo gave, offered, or
    agreed to give the thing of value before,
    after, or at the same time as the business,
    transaction, or series of transactions.
    Therefore, the government does not need to
    prove that defendant Bravo gave, offered, or
    agreed to offer the trip to Las Vegas before
    defendant Martínez performed any official
    action or series of acts.
    (Emphases added.)   Paragraph eleven of Jury Instruction 21 appears
    to have a purpose similar to that of paragraph ten of Jury
    Instruction 20, though paragraph eleven is concerned with the
    timing of Defendant Martínez's solicitation, demand, acceptance, or
    agreement to accept the thing of value:
    When considering the Second and Third
    elements above, I instruct you that a
    defendant is not required to have accepted or
    received a thing of value before the business,
    transaction, or series of transactions.
    Rather,    the  Government   may   prove   that
    defendant    Martínez   solicited,    demanded,
    accepted, or agreed to accept the thing of
    value before, after, or at the same time as
    the business, transaction, or series of
    transactions. Therefore, the Government does
    not need to prove that defendant Martínez
    solicited, demanded, accepted or agreed to
    accept the trip to Las Vegas before defendant
    Martínez performed any official act or series
    of acts.
    (Emphases added.)
    The final relevant instruction is Jury Instruction 22,
    titled simply "Bribery."   This instruction states in full:
    -30-
    I have used the word "bribery" in these
    instructions. Bribery requires that the
    government prove beyond a reasonable doubt the
    existence of a quid pro quo or, in plain
    English, an agreement that the thing of value
    that is given to the public official is in
    exchange for that public official promising to
    perform official acts for the giver. It is
    not sufficient that the thing of value is made
    to curry favor because of the official's
    position or that there is some connection in
    time or place with an official act that is
    promised to the giver; rather there must be an
    agreement that the thing of value was offered
    by defendant Bravo and accepted by Senator
    Martínez in exchange for a promise to perform
    an official act.
    Defendants maintain that the district court's directions
    in Jury Instructions 20 and 21 allowed the jury to convict Martínez
    and Bravo of a gratuity offense.      They argue that a permissible
    construction of Jury Instruction 20 could read as follows:
    [T]he Government may prove that defendant
    Bravo . . . offered . . . the thing of value
    . . . after . . . the business, transaction,
    or series of transactions.    Therefore, the
    government does not need to prove that
    defendant Bravo . . . offered . . . the trip
    to Las Vegas before defendant Martínez
    performed any official action or series of
    acts.
    Similarly, Jury Instruction 21 could be read to state:
    [T]he Government may prove that defendant
    Martínez . . . agreed to accept the thing of
    value . . . after . . . the business,
    transaction, or series of transactions.
    Therefore, the Government does not need to
    prove that defendant Martínez . . . agreed to
    accept the trip to Las Vegas before defendant
    Martínez performed any official act or series
    of acts.
    -31-
    Defendants argue that if Bravo had not offered Martínez anything
    before   Martínez   performed   an     official   act,   and   Martínez   had
    therefore not accepted (or even agreed to accept) anything from
    Bravo before performing that act, any subsequent offer of a thing
    of value from Bravo to Martínez cannot be construed as a bribe.
    Instead, the offer would merely be an offer of a reward for an act
    taken by Martínez in the past.         This, Defendants maintain, is an
    offer of a gratuity, not a bribe.
    The   government    does     not   explicitly      address    this
    potentially problematic construction of paragraph ten of Jury
    Instruction 20 and paragraph eleven of Jury Instruction 21.                It
    argues that the titles of those instructions -- "Bribery Concerning
    Programs Receiving Federal Funds, 18 U.S.C. § 666(a)(2)" and
    "Bribery Concerning Programs Receiving Federal Funds, 18 U.S.C.
    § 666(a)(1)(B)" -- make clear that the jury must find bribery, not
    a mere gratuity.      Additionally, the government points to the
    unambiguous quid pro quo language of Jury Instruction 22, which, it
    claims, leaves no doubt that the jury was required to find bribery
    to convict Defendants of violating § 666.
    Relatedly, Defendants maintain that the effect of the
    alleged errors in Jury Instructions 20 and 21 was magnified by
    certain statements made by the government during its closing
    argument.    Defendants point to the government's statement to the
    jury that
    -32-
    it doesn't matter when it was offered or when
    it was accepted . . . . These instructions
    clarify that -- that it doesn't matter if the
    trip was offered before official acts were
    taken, at the same time official acts were
    taken, or after official acts were taken,
    because the crime is offering or accepting the
    trip with intent to influence or reward.
    (Emphasis added.)   This language, Defendants posit, suggests that
    the government need only prove a "connection" between the official
    acts and the offer of the Las Vegas trip, rather than a causal
    relationship.   Defendants argue that the government essentially
    told the jurors that they could convict Martínez and Bravo of
    violating § 666 if they found that a mere gratuity -- as opposed to
    a bribe -- was offered by Bravo and accepted by Martínez.
    2. Analysis
    The Supreme Court explained the distinction between
    bribes and illegal gratuities in United States v. Sun-Diamond
    Growers of California, 
    526 U.S. 398
    (1999):
    The distinguishing feature of each crime is
    its intent element. Bribery requires intent
    "to influence" an official act or "to be
    influenced" in an official act, while illegal
    gratuity requires only that the gratuity be
    given or accepted "for or because of" an
    official act. In other words, for bribery
    there must be a quid pro quo -- a specific
    intent to give or receive something of value
    in exchange for an official act. An illegal
    gratuity, on the other hand, may constitute
    merely a reward for some future act that the
    public official will take (and may already
    have determined to take), or for a past act
    that he has already taken.
    -33-
    
    Id. at 404-05 (third
    emphasis added) (construing the general
    federal bribery and gratuity statute, 18 U.S.C. § 201);   see also
    United States v. Mariano, 
    983 F.2d 1150
    , 1159 (1st Cir. 1993)
    (noting in a § 666 case that "[t]he essential difference between a
    bribe and an illegal gratuity is the intention of the bribe-giver
    to effect a quid pro quo").     As the Eighth Circuit has noted,
    "[t]he core difference between a bribe and a gratuity is not the
    time the illegal payment is made, but the quid pro quo, or the
    agreement to exchange [a thing of value] for official action."
    United States v. Griffin, 
    154 F.3d 762
    , 764 (8th Cir. 1998).
    Although the timing of the payment may not provide a conclusive
    answer as to whether that payment is a bribe or a gratuity, the
    timing of the agreement to make or receive a payment may: one
    cannot agree to perform an act in exchange for payment when that
    act has already been performed.    Therefore, if the agreement to
    exchange a thing of value for an act is made after that act has
    been performed, that agreement cannot be properly viewed as an
    agreement to offer or accept a bribe.
    With this distinction in mind, it is clear that paragraph
    ten of Jury Instruction 20 and paragraph eleven of Jury Instruction
    21 told the jury that Bravo could be convicted under § 666 for
    agreeing to give Martínez a gratuity, and that Martínez could be
    convicted under § 666 for agreeing to accept the same.    Paragraph
    ten explains that for a conviction under § 666, the government need
    -34-
    not prove that Bravo offered or agreed to give Martínez anything of
    value before the transaction that was the subject of the "payment"
    took place, and that it is sufficient for conviction to show that
    Bravo "offered, or agreed to give the thing of value . . . after
    . . . the . . . transaction." Similarly, paragraph eleven suggests
    that the government need not prove that Martínez accepted or agreed
    to accept the thing of value before he performed the act that was
    the subject of the "payment," and that it is sufficient to show
    that Martínez "agreed to accept the thing of value . . . after
    . . . the transaction."
    This view of the requirements of § 666 was reinforced by
    the   government's    closing      argument.      Like    the   court's   jury
    instructions, significant portions of the government's closing
    argument were consistent with a bribery theory under § 666.
    However, in emphasizing that "it doesn't matter if the trip was
    offered . . . after official acts were taken," the government
    invited the jury to find guilt based on a gratuity theory of
    liability.
    While the language in Jury Instruction 22 correctly
    states the requirements for a bribery conviction, it was not
    sufficient     to   offset   the    flatly     contrary   language   in   Jury
    Instructions 20 and 21.            This is particularly so because the
    gratuities theory was offered in the instructions on the § 666
    counts themselves, whereas the correct bribery language was in a
    -35-
    subsequent global instruction that applied to both the Puerto Rico
    and federal bribery counts.
    Importantly,   the     evidence     presented   at   trial   could
    support a finding that the "payment" Bravo gave and Martínez
    received constituted a gratuity. The evidence showed that Martínez
    supported the Senate Projects after the Las Vegas trip -- he voted
    in support of both bills within a week of returning -- which is
    consistent with a quid pro quo, and therefore with a bribery
    theory.      However, he first took actions in support of Senate
    Projects 410 and 471 -- such as submitting the bills to the Senate
    --   weeks   or   months   before   the   trip    to   Las   Vegas,   which   is
    consistent with a gratuity theory.             Hence, the jury reasonably
    could have found that the trip was a reward for that prior conduct,
    rather than the quid pro quo for Martínez's later support of the
    bills.
    Although the instructions allowed the jury to convict
    Bravo and Martínez of violating § 666 by giving or accepting
    gratuities, there remains the more difficult question of whether
    this instruction was legally erroneous.                We have never decided
    whether § 666 criminalizes gratuities in addition to bribes, as the
    issue has never been squarely before us.                We now turn to that
    question.
    -36-
    B. Section 666
    1. Statutory Context
    We ordinarily begin with the plain language of a statute
    in assessing its meaning.      See United States v. Lachman, 
    387 F.3d 42
    , 50 (1st Cir. 2004).            Here, however, much of the relevant
    language originates in another provision, 18 U.S.C. § 201, and it
    is therefore useful to take a step back and place § 666 into
    statutory context before looking at its specific language.
    Section    666   "was    born    as   the   stepchild    of   another
    statute, 18 U.S.C. § 201."     Justin Weitz, Note, The Devil is in the
    Details: 18 U.S.C. § 666 after Skilling v. United States, 14 N.Y.U.
    J. Legis. & Pub. Pol'y 805, 816 (2011).            Section 201 criminalizes
    bribes and gratuities on the part of federal officials.                     The
    statute   separates   the    crimes    of    illegal    bribes     and   illegal
    gratuities into two sections: § 201(b) outlaws the offering of
    bribes to public officials, as well as the acceptance of bribes by
    those officials, while § 201(c) outlaws the offering and acceptance
    of illegal gratuities.      18 U.S.C. § 201(b), (c).
    The scope of § 201 is limited to those "acting for or on
    behalf of the United States."          As the Senate Report for § 666
    noted:
    With respect to bribery, 18 U.S.C. 201
    generally punishes corrupt payments to federal
    public officials, but there is some doubt as
    to whether or under what circumstances persons
    not employed by the federal government may be
    considered as a "public official" under the
    -37-
    definition in 18 U.S.C. 201(a) as anyone
    "acting for or on behalf of the United States,
    or any department, agency or branch of
    government thereof, including the District of
    Columbia, in any official function."       The
    courts of appeals have divided on the question
    whether a person employed by a private
    organization receiving Federal monies pursuant
    to a program is a "public official" for
    purposes of section 201.
    S. Rep. No. 98-225, at 369 (1983), reprinted in 1984 U.S.C.C.A.N.
    3182, 3510.      Spurred by the Supreme Court's pending consideration
    of the meaning of § 201 in Dixson v. United States, 
    465 U.S. 482
    (1984), which sought to resolve whether § 201 applied to state and
    local      officials,    Congress     created     §   666     as     part   of   the
    Comprehensive Crime Control Act of 1984 ("CCCA"), Pub. L. No.
    98-473, 98 Stat. 1837 (1984).         According to the Senate Report, the
    purpose of § 666 was to "augment the ability of the United States
    to   vindicate    significant       acts   of   theft,      fraud,    and   bribery
    involving      Federal    monies     which      are   disbursed        to   private
    organizations or State and local governments pursuant to a Federal
    program."11    S. Rep. No. 98-225 at 369; 1984 U.S.C.C.A.N. at 3510.
    Significantly, the Senate Report stated that § 666 was to be
    interpreted "consistent with the purpose of this section to protect
    the integrity of the vast sums of money distributed through Federal
    11
    Section 666 has a separate provision that covers theft and
    fraud.   See 18 U.S.C. § 666(a)(1)(A).     That provision is not
    implicated in this case.
    -38-
    programs from theft, fraud, and undue influence by bribery."              S.
    Rep. No. 98-225 at 370; 1984 U.S.C.C.A.N. at 3511 (emphasis added).
    As originally enacted as part of the CCCA, the 1984
    version of § 666 differed somewhat from the current law.                 For
    instance, what is now § 666(a)(2) was originally § 666(c), which
    read in relevant part:
    (c) Whoever offers, gives or agrees to give an
    agent of an organization or of a State or
    local government agency . . . anything of
    value for or because of the recipient's
    conduct in any transaction or matter or any
    series of transactions or matters involving
    $5,000 or more concerning the affairs of such
    organization or State or local government
    agency, shall be imprisoned not more than ten
    years or fined not more than $100,000 . . . .
    18 U.S.C. § 666(c) (1984) (emphasis added).            Section 666 was
    amended in 1986 as part of the Criminal Law and Procedure Technical
    Amendments Act of 1986 ("CLPTA"), Pub. L. No. 99-646, 100 Stat.
    3592 (1986).    The House Report noted that "the enactment of the
    CCCA came during the final weeks of the 98th Congress, and, due to
    demanding   time   constraints,   the    CCCA   contained   a   number   of
    ambiguities and technical defects."       H.R. Rep. No. 99-797, at 16
    (1986), reprinted in 1986 U.S.C.C.A.N. 6138.         The purpose of the
    CLPTA was "to eliminate these technical defects and to make minor
    substantive revisions."    
    Id. With respect to
    § 666 specifically,
    the House Report clarified that section 42 of the CLPTA amended the
    statute "to avoid its possible application to acceptable commercial
    and business practices." 
    Id. at 30. The
    Report explained further:
    -39-
    18 U.S.C. 666 prohibits bribery of certain
    public officials, but does not seek to
    constrain    lawful     commercial    business
    transactions. Thus, 18 U.S.C. 666 prohibits
    corruptly giving or receiving anything of
    value for the purpose of influencing or being
    influenced in connection with any business,
    transaction, or series of transactions. The
    provision parallels the bank bribery provision
    (18 U.S.C. 215).
    
    Id. at 30 n.9
    (emphasis added).
    Two    changes    to   §     666   effected    by   the   CLPTA     are
    noteworthy.     First, the "for or because of" language was replaced
    with "intending to be influenced or rewarded" in § 666(a)(1)(B)
    (the provision applicable to agents) and "with intent to influence
    or   reward"   in    §    666(a)(2)      (the   provision   applicable      to   the
    individual offering the agent something of value).                This change is
    especially notable, as the pre-amendment language was similar to
    that found in 18 U.S.C. § 201(c) -- § 201's gratuity provision.
    Section 201(c)(1)(A) prohibits one from "giv[ing], offer[ing], or
    promis[ing] anything of value to any public official . . . for or
    because of any official act performed or to be performed by such
    public official," 18 U.S.C. § 201(c)(1)(A), and the complementary
    subsection prohibits public officials from "demand[ing], seek[ing],
    receiv[ing],       accept[ing],     or    agree[ing]   to   receive    or   accept
    anything of value . . . for or because of any official act," 
    id. § 201(c)(1)(B). Section
    666's post-amendments language is much
    closer to that found in 18 U.S.C. § 201(b) -- § 201's bribery
    provision.      It imposes punishment on one who gives or offers
    -40-
    anything of value to a public official "with intent . . . to
    influence" an official act, 
    id. § 201(b)(1)(A), and
    on a public
    official who agrees to accept a thing of value "in return for
    . . . being influenced in the performance of any official act," 
    id. § 201(b)(2)(A). As
    the Supreme Court noted in Sun-Diamond,
    § 201(b)'s intent language implies that "for bribery there must be
    a quid pro quo -- a specific intent to give or receive something of
    value in exchange for an official 
    act." 526 U.S. at 404-05
    .
    The second relevant alteration is the addition of the
    word "corruptly" to the beginning of § 666(a)(1)(B) and (a)(2).
    Congress neither explained the reason for this change nor defined
    the term.   However, this is another instance where the language of
    § 666 was amended in a way that brought the statute closer to
    § 201's bribery provision.       Section 201(b)(1) punishes one who
    "corruptly gives, offers or promises anything of value to any
    public official," 
    id. § 201(b)(1) (emphasis
    added), and punishes a
    public official who "corruptly demands, seeks, receives, accepts,
    or agrees to receive or accept anything of value," 
    id. § 201(b)(2) (emphasis
      added).     The   word    "corruptly"   does   not   appear   in
    § 201(c), the gratuities provision.
    With this background in mind, we now analyze the text and
    structure of the statute.
    -41-
    2. The Meaning of § 666
    The text of § 666 has remained largely unchanged since
    the 1986 amendments. Today, the statute reads in relevant part:
    (a) Whoever . . . --
    (1) being an agent of an organization, or of a
    State, local, or Indian tribal government, or any
    agency thereof--
    . . . .
    (B) corruptly solicits or demands for the
    benefit of any person, or accepts or agrees
    to accept, anything of value from any person,
    intending to be influenced or rewarded in
    connection with any business, transaction, or
    series of transactions of such organization,
    government, or agency involving anything of
    value of $5,000 or more; or
    (2) corruptly gives, offers, or agrees to give
    anything of value to any person, with intent to
    influence or reward an agent of an organization or
    of a State, local or Indian tribal government, or
    any agency thereof, in connection with any
    business, transaction, or series of transactions
    of such organization, government, or agency
    involving anything of value of $5,000 or more;
    shall be fined under this title, imprisoned not more than
    10 years, or both.
    18 U.S.C. § 666(a).       One of the most conspicuous differences
    between the texts of § 666 and § 201 concerns the intent element:
    while § 666 prohibits one from corruptly offering a thing of value
    with intent to "influence or reward" an agent, and prohibits an
    agent from corruptly soliciting or demanding a thing of value with
    intent to be "influenced or rewarded," the bribery provision
    applicable to federal officials, § 201(b), does not include the
    -42-
    alternative "reward": it prohibits one from corruptly offering a
    thing of value with intent to "influence" an act, and prohibits an
    official from corruptly soliciting a thing of value with an intent
    to be "influenced."       The word "reward" in § 666 is open to (at
    least) two different interpretations.12
    Under the first interpretation, when a payor intends to
    influence an official's future actions, the payment constitutes a
    bribe; when a payor intends to reward the official's past conduct
    (or future conduct the official is already committed to taking),
    the payment constitutes a gratuity. United States v. Anderson, 
    517 F.3d 953
    , 961 (7th Cir. 2008).       Several circuits have adopted this
    reading of the language.         Id.; United States v. Ganim, 
    510 F.3d 134
    , 150 (2d Cir. 2007) ("[A] payment made to 'influence' connotes
    bribery, whereas a payment made to 'reward' connotes an illegal
    gratuity."); United States v. Zimmerman, 
    509 F.3d 920
    , 927 (8th
    Cir.    2007)   (citing   §   666(a)(1)(B)'s   "influenced   or   rewarded"
    language in support of finding that "Section 666(a)(1)(B) prohibits
    both the acceptance of bribes and the acceptance of gratuities
    intended to be a bonus for taking official action"); United States
    v. Agostino, 
    132 F.3d 1183
    , 1195 (7th Cir. 1997).
    Under the second interpretation, the word "reward" does
    not create a separate gratuity offense in § 666, but rather serves
    12
    Unfortunately, the legislative history contains no clues
    about why this word was added in the 1986 amendments.
    -43-
    a more modest purpose: it merely clarifies "that a bribe can be
    promised before, but paid after, the official's action on the
    payor's behalf."      United States v. Jennings, 
    160 F.3d 1006
    , 1015
    n.3 (4th Cir. 1998). "This definition accords with the traditional
    meaning of the term 'reward' as something offered to induce another
    to act favorably on one's behalf (for example, a bounty offered for
    the capture of a fugitive)."             
    Id. Under this reading,
    the terms
    "influence"   and    "reward"          each    retain    independent     meaning.
    "Influence" would be used in situations in which, for instance, a
    payment was made to a local government commissioner in order to
    induce him to vote in a certain way on a particular matter.
    "Reward" would be used if a promise of payment was made, contingent
    upon that commissioner's vote; once the commissioner voted in the
    way the payor requested, a "reward" would follow.                     Both of these
    situations involve a quid pro quo, and both therefore constitute
    bribes.   What matters, of course, is that the offer of payment
    precedes the official act.
    Moreover,         a    reading        consistent     with    the    second
    interpretation      would       help    to     explain   the   presence      of   the
    "corruptly" language in § 666(a)(1)(B) and (a)(2).                     As discussed
    supra, § 201 uses the word corruptly only in its bribery provision,
    § 201(b), not in the gratuity provision, § 201(c).                      The Fourth
    Circuit puzzled over this issue in United States v. Jennings,
    "namely, why § 666(a)(2)'s language prohibiting 'rewards' given
    -44-
    'corruptly' should be interpreted to cover gratuities, when under
    § 201 any payment made 'corruptly' is a bribe, not an illegal
    gratuity."   
    Id. (emphasis added). If
    the inclusion of the word
    "reward" in § 666 does no more than clarify that the payment of a
    bribe can occur after the act that is the subject of the bribe is
    completed (so long as the agreement to pay the bribe for the act or
    acts is made before the act or acts takes place), the statute still
    applies only to bribery, and the use of the word "corruptly" in
    § 666 would comport with the use of the same word in § 201(b): any
    payment made "corruptly" is a bribe.13   Cf. 
    Anderson, 517 F.3d at 13
           The Second Circuit took a different view of "corruptly," in
    keeping with its prior conclusion that § 666 covers gratuities. In
    United States v. Bahel, the Second Circuit rejected the defendant's
    argument that the jury charge should have specified that the
    government needed to prove that he "'had been "corrupted" at the
    time he acted in his official business.'" 
    662 F.3d 610
    , 638 (2d
    Cir. 2011) (emphasis added). Instead, the court concluded that "in
    the case of a gratuity, the corrupt intent required under Section
    666 refers to an individual's state of mind at the time the payment
    is received."    
    Id. (emphasis added). This
    interpretation of
    "corruptly" is at odds with that of the Fourth Circuit in Jennings,
    which would appear to require the corrupt intent at the time the
    agent engages in the act that is the subject of the reward. While
    Bahel's definition of "corruptly" supports the Second Circuit's
    interpretation of § 666 as criminalizing gratuities as well as
    bribes, the question raised in Jennings remains: if "corruptly" in
    fact means nothing more than a lack of an innocent motive at the
    time one receives payment, why does § 201 -- the statute upon which
    § 666 is based -- fail to include that language in its gratuity
    provision when it is included in § 201's bribery provision? In
    other words, although the Second Circuit provides an avenue by
    which the word "corruptly" could be given independent meaning
    without cabining § 666 to bribery, that interpretation would seem
    to vitiate the independent meaning of the same word in § 201 --
    again, an important consideration given that § 666 was based on
    § 201.
    -45-
    961 ("Unlike a gratuity, a bribe is a payment made with 'a corrupt
    purpose, such as inducing a public official to participate in a
    fraud or to influence his official action.'" (quoting U.S.S.G.
    § 2C1.1 cmt. background)).
    Another critical difference between § 666 and § 201 is
    the maximum penalty authorized under the statutes.                   One who
    violates § 201(b), the bribery provision, may be fined, "or
    imprisoned for not more than fifteen years, or both."              18 U.S.C.
    § 201(b) (emphasis added).        For a violation -- any violation -- of
    § 666, the statute provides a punishment of a fine, a term of
    imprisonment of "not more than 10 years," or both.              
    Id. § 666(a) (emphasis
    added).     An even more striking difference in penalties,
    however, exists between § 666 and § 201's gratuity subsection, the
    latter of which calls for a term of imprisonment of "not more than
    two years," 
    id. § 201(c) (emphasis
    added) -- meaning that § 666
    authorizes a term of imprisonment five times longer than that
    allowed by § 201's gratuities provision.
    This dramatic discrepancy in maximum penalties between
    § 666 and § 201(c) makes it difficult to accept that the statutes
    target   the   same   type   of   crime    --   illegal    gratuities.   The
    difference in sentences contemplated by § 201(b) and § 666 is both
    less dramatic and more understandable: § 201(b) targets (primarily)
    federal officials, while § 666 targets non-federal officials who
    happen to have a connection to federal funds.             It is reasonable to
    -46-
    assume that the federal government viewed corrupt federal officials
    involved in the receipt of bribes as more culpable.14
    The    distinct   penalties     for    bribes   and    gratuities
    contained in § 201 highlights an obvious yet important structural
    difference between §§ 666 and 201: § 666 does not have separate
    bribery and gratuity subsections.         For those circuits that have
    found that § 666 criminalizes gratuities, two subsections of § 666
    do the same work as four subsections of § 201.                  We think it
    unlikely that Congress would condense two distinct offenses into
    the same subsection in § 666 when the statute upon which it is
    based has separate subsections for each offense.            See George D.
    Brown, Stealth Statute -- Corruption, the Spending Power, and the
    Rise of 18 U.S.C. § 666, 73 Notre Dame L. Rev. 247, 310 (1998)
    ("Congress did not . . . enact a mirror image of § 201 for
    nonfederal officials. Section 201 contains separate subsections to
    deal with bribery and gratuities.        Section 666 does not.      It is a
    mistake to attempt to read the two statutes as equal in reach.").
    Furthermore,    if   Congress   did   choose    to   condense   bribes   and
    gratuities into a single provision in § 666, it would be odd to do
    so by merely plugging slightly modified language from § 201(b), its
    bribery provision, into the statute. Surely the word "gratuity" --
    14
    The legislative history of § 666 sheds no light on the
    reason for these differences in penalties.
    -47-
    which is, of course, mentioned nowhere in the text or legislative
    history of § 666 -- was not foreign to Congress in 1986.
    Although § 666 was enacted to supplement § 201, we can
    easily hypothesize at least two reasons why Congress may have
    chosen to supplement only § 201's prohibition of bribery.               First,
    bribes are simply worse than illegal gratuities.             See 
    Sun-Diamond, 526 U.S. at 405
    (noting the difference in the maximum sentences
    allowed under § 201(b) and (c) and stating that "[t]he punishments
    prescribed     for   the     two    offenses       reflect   their     relative
    seriousness"); Charles N. Whitaker, Note, Federal Prosecution of
    State and Local Bribery: Inappropriate Tools and the Need for a
    Structured Approach, 
    78 Va. L
    . Rev. 1617, 1622 (1992) ("The typical
    one- to two-year penalty under gratuities statutes evidences the
    lesser degree of culpability in accepting a gratuity as opposed to
    a bribe."). Under this theory, Congress may have viewed bribery as
    far more of a threat to the proper functioning of federally funded
    programs than gratuities.          Because the application of § 666 to
    gratuities offenses would "take[] the statute deeply into a range
    of government ethics issues that may be better handled at the state
    level," Congress may have intended to cabin § 666 "to the hard-core
    area   of   bribery[,]     where   any   federal    interest   in    government
    integrity will be stronger."             
    Brown, supra, at 310
    (footnote
    omitted).
    -48-
    A second (and related) reason why Congress may have
    limited § 666 to bribery is to avoid what has been characterized as
    federal overcriminalization.       See generally 
    Weitz, supra, at 840
    ;
    Alex   Kozinski    &   Misha   Tseytlin,   You're   (Probably)   a   Federal
    Criminal, in In the Name of Justice 43-56 (Timothy Lynch ed.,
    2009); Sanford H. Kadish, Comment: The Folly of Overfederalization,
    46 Hastings L.J. 1247, 1249-50 (1995).         In other words, Congress
    may have been wary of venturing too far into the thickets of state
    and local corruption, which often implicate the political processes
    of the state.     See 
    Brown, supra, at 310
    .
    In Sun-Diamond, a case addressing the scope of § 201's
    gratuity provision, the Supreme Court noted that,
    when Congress has wanted to adopt . . . a
    broadly prophylactic criminal prohibition upon
    gift giving, it has done so in a more precise
    and more administrable fashion.
    . . .
    [Because] this is an area where precisely
    targeted prohibitions are commonplace, and
    where more general prohibitions have been
    qualified by numerous exceptions . . . a
    statute in this field that can linguistically
    be interpreted to be either a meat axe or a
    scalpel should reasonably be taken to be the
    
    latter. 526 U.S. at 408
    , 412.      Here, too, we feel obligated to choose the
    scalpel.   Other than the ambiguous use of the word "rewarded," the
    text of § 666, as well as its legislative history and purpose, do
    not support the argument that Congress intended the statute to
    -49-
    reach gratuities.   The statute was amended in a way that brought
    its language closer to § 201's bribery provision, and further from
    § 201's gratuity provision, suggesting the true targets of § 666
    are bribes, not gratuities.         Critically, accepting that § 666
    criminalizes   gratuities   would    expose   defendants   convicted   of
    gratuities violations under § 666 to penalties far greater than
    those faced by individuals convicted of gratuities violations under
    § 201 -- a strange outcome that we doubt Congress intended.            We
    therefore hold that gratuities are not criminalized under § 666.15
    15
    We have two responses to the thoughtful concurrence of our
    colleague that the statute is unclear enough that the rule of
    lenity precludes Defendants' convictions to the extent that they
    could have rested on a gratuity. First, the rule of lenity is
    rarely applied, and should be reserved for situations in which,
    "after considering text, structure, history, and purpose, there
    remains a grievous ambiguity or uncertainty in the statute such
    that the Court must simply guess as to what Congress intended."
    Barber v. Thomas, 
    130 S. Ct. 2499
    , 2509-10 (2010) (citations
    omitted) (internal quotation marks omitted); see also Muscarello v.
    United States, 
    524 U.S. 125
    , 138-39 (1998) ("The simple existence
    of some statutory ambiguity . . . is not sufficient to warrant
    application of that rule, for most statutes are ambiguous to some
    degree."); United States v. Jimenez, 
    507 F.3d 13
    , 21 (1st Cir.
    2007) ("[G]enuine ambiguity requires more than a possible
    alternative construction."); accord United States v. Flemming, 
    617 F.3d 252
    , 272 (3d Cir. 2010) (noting that "[a]pplication of the
    rule of lenity is called for only in rare cases").         We have
    construed § 666 using traditional tools of construction and find no
    grievous ambiguity or uncertainty.           Lenity is therefore
    inapplicable. See 
    Councilman, 418 F.3d at 83
    .
    Second, we acknowledge, as our colleague notes, that the
    Federal Sentencing Guidelines Manual applies separate guidelines
    for bribes and gratuities under § 201, and it states that both of
    these guidelines are applicable to § 666.          U.S. Sentencing
    Guidelines Manual app. A (2011). Some have suggested that this
    determination on the part of the Sentencing Commission "weighs in
    favor of a conclusion that § 666 encompasses bribes and
    gratuities."     See, e.g., Mark S. Gaioni, Note, Federal
    -50-
    C. Conclusion
    Given this holding, the language in paragraph ten of Jury
    Instruction 20 and paragraph eleven of Jury Instruction 21 had no
    place in the § 666 instructions.        By including that language, the
    court improperly invited the jury to convict both Martínez and
    Bravo   for    conduct   involving   gratuities   rather   than   bribes.
    Consequently, the jury was allowed to convict Martínez and Bravo on
    a legally erroneous theory.          Although other parts of the jury
    instructions accurately stated the requirements for a bribery
    conviction, the fact remains that the jury was confronted with the
    flatly contrary instructions in paragraph ten of Jury Instruction
    Anticorruption Law in the State and Local Context: Defining the
    Scope of 18 U.S.C. § 666, 46 Colum. J. L. & Soc. Probs. 207, 239-41
    (2012). We disagree. The Sentencing Commission is in the business
    of "establish[ing] sentencing policies and practices for the
    Federal criminal justice system" and "develop[ing] means of
    measuring the degree to which the sentencing, penal, and
    correctional practices are effective," 28 U.S.C. § 991(b); it is
    not in the business of determining what type of conduct a statute
    does and does not criminalize.       See, e.g., United States v.
    Morales, 
    590 F.3d 1049
    , 1052 (9th Cir. 2010) ("Of course, the
    Commission can't tell federal courts how to interpret statutes.").
    The Commission's choice to apply the gratuities guideline to § 666
    therefore carries no weight in our analysis.       Cf. DePierre v.
    United States, 
    131 S. Ct. 2225
    , 2236 (2011) ("We have never held
    that, when interpreting a criminal statute, deference is warranted
    to the Sentencing Commission's definition of the same term in the
    Guidelines."); United States v. Gowing, 
    683 F.3d 406
    , 410 (2d Cir.
    2012) ("The Sentencing Commission, which promulgates the
    Guidelines, is entitled to no deference when it interprets criminal
    statutes."); United States v. Palacio, 
    4 F.3d 150
    , 155 (2d Cir.
    1993) ("[U]nless the Sentencing Commission is construing its own
    authority as an agency, its view of the substantive meaning of a
    criminal statute is unlikely to be entitled to any deference."
    (internal citations omitted)).
    -51-
    20 and paragraph eleven of Jury Instruction 21.              As noted, the
    government's   closing   argument    improperly    invited    the   jury   to
    convict the Defendants on the proscribed "gratuity theory," and the
    evidence presented at trial could support a finding that the
    "payment" Bravo gave and Martínez received constituted a gratuity.
    
    See supra
    Part III(A)(2). Under these circumstances, we cannot say
    "with fair assurance, after pondering all that happened without
    stripping the erroneous action from the whole, that the judgment
    was not substantially swayed by the error."16        Kotteakos v. United
    States, 
    328 U.S. 750
    , 765 (1946).          We therefore conclude that we
    must vacate Defendants' convictions under § 666 because of the
    deficiencies in Jury Instructions 20 and 21.         See Fiore v. White,
    
    531 U.S. 225
    , 228 (2001) (holding that conviction of defendant for
    conduct that a "criminal statute, as properly interpreted, does not
    prohibit . . . violate[s] due process").
    16
    Even if a defendant has properly preserved his objection to
    an incorrect jury instruction, we will not set aside the verdict if
    we find that the error was harmless. United States v. Sasso, 
    695 F.3d 25
    , 29 (1st Cir. 2012). However, we measure harmless error in
    a criminal case using two distinct standards.         The stricter
    standard, known as the Chapman standard, is "applicable mainly to
    issues of constitutional dimension, [and] requires the government
    to prove beyond a reasonable doubt that the error did not influence
    the verdict." Id.; see Chapman v. California, 
    386 U.S. 18
    , 23-24
    (1967).    The less stringent standard we cite above, called the
    Kotteakos standard, is "applicable mainly to trial errors that are
    not of constitutional dimension." 
    Sasso, 695 F.3d at 29
    . Here it
    makes no difference what standard we apply because, even assuming
    the applicably of the less stringent Kotteakos standard, the error
    was not harmless. See 
    id. -52- IV. Defendants
      argue   that    their   convictions   should   be
    reversed because the indictment was barred by the statute of
    limitations.   The alleged unlawful conduct at issue took place
    through May 2005.   The indictment against Defendants was returned
    on June 22, 2010, more than five years after the conduct occurred.
    Pursuant to 18 U.S.C. § 3282(a), "[e]xcept as otherwise expressly
    provided by law, no person shall be prosecuted, tried, or punished
    for any offense, not capital, unless the indictment is found or the
    information is instituted within five years next after such offense
    shall have been committed."     However, Defendants signed tolling
    agreements waiving their right to allege an affirmative defense
    based on the statute of limitations.17 Defendants maintain that (1)
    the tolling agreements were void because they were not properly
    executed by the government, and (2) even if they were not void, the
    tolling agreements did not extend the statute of limitations period
    for a gratuity theory of liability on the § 666 counts.
    "We review de novo a district court's decision not to
    dismiss on statute of limitations grounds."          United States v.
    Munoz-Franco, 
    487 F.3d 25
    , 52 (1st Cir. 2007); see also United
    17
    The record does not disclose the precise reason why
    Defendants signed the tolling agreements.       However, "[s]uch
    agreements are typically entered into . . . in exchange for the
    government's agreement not to indict before a certain time in the
    hope that further discussion may result in a more favorable
    disposition or prevent an indictment altogether."      Robert S.
    Hunter, Fed. Trial Handbook: Criminal § 12:28 (2012).
    -53-
    States v. Spector, 
    55 F.3d 22
    , 25 (1st Cir. 1995) (applying de novo
    review to question of whether tolling agreement was effective
    waiver   of    defendant's   rights   under   statute   of    limitations).
    Defendants argue that the tolling agreements never became effective
    because, although both Defendants and their attorneys signed them,
    they were never signed by the government.        They rely primarily on
    our opinion in United States v. Spector to support this argument.
    In Spector, the government and the defendants sought to enter into
    a tolling agreement that would bar the application of the § 3282
    limitations 
    period. 55 F.3d at 23
    .    That agreement provided that
    it would be effective "'upon execution by [the defendants] and
    their respective counsel and the United States by its counsel.'"
    
    Id. at 24. The
    agreement was signed by the defendants and their
    counsel, but not by counsel for the government.         
    Id. We found that
    the tolling agreement was ineffective, pointing to, inter alia, the
    unambiguous language in the agreement.        
    Id. at 25. Defendants
    argue unpersuasively that we should extend
    Spector to the facts of this case.        We summarized our holding in
    Spector as follows: "[w]here the parties have so deliberately set
    forth in writing the conditions necessary to make their agreement
    effective, we think it inadvisable for a court to condone deviation
    from one of the explicit terms, absent some good reason to do so."
    
    Id. We also explicitly
    limited our holding:
    We emphasize that we are not saying that, to
    be enforced, an agreement to extend the
    -54-
    statute of limitations must be made in
    writing, or must be signed by the government.
    We say only that, where the parties themselves
    have chosen to set forth the terms in writing,
    it makes sense to hold them to those terms,
    absent good reason to do otherwise.
    
    Id. at 26 n.4
    (citations omitted).
    Defendants' tolling agreements in the present case state:
    "By signing this document, I knowingly and voluntarily waive any
    rights I may have under the statute of limitations regarding
    charges which may result from the grand jury investigation . . .
    provided that such charges are brought on or before June 25, 2010."
    (Emphasis added.)    The agreements thus make clear that their
    provisions will go into effect when signed by Defendants; nothing
    in the agreements require counsel for the United States to sign the
    document as a condition of enforceability.      We therefore conclude
    that the failure of the government to sign the tolling agreements
    does not render them invalid.
    As to Defendants' second argument, we need not determine
    whether the tolling agreements cover a gratuity theory of liability
    under § 666, as we have found that § 666 does not criminalize
    gratuities. The government may not pursue a conviction on that
    ground if Defendants are retried.
    V.
    Bravo   challenges    his    conviction   on   count   one   for
    conspiracy to violate the Travel Act, claiming that he is entitled
    to a judgment of acquittal on that count.
    -55-
    A. Background
    Count one of the indictment charged Bravo with conspiring
    with Martínez and de Castro Font to commit two different crimes:
    (1) bribery in violation of § 666 and (2) traveling in interstate
    commerce in violation of 18 U.S.C. § 1952 ("the Travel Act").       A
    Travel Act charge must identify an unlawful purpose for the
    travel,18 and the Travel Act conspiracy alleged against Bravo
    specified that his travel was to aid "racketeering" -- a term that
    covers various types of unlawful activity.19 In this case, the only
    18
    Section 1952, which is titled "Interstate and foreign travel
    or transportation in aid of racketeering enterprises," states, in
    pertinent part:
    (a) Whoever travels in interstate or foreign commerce or
    uses the mail or any facility in interstate or foreign
    commerce, with intent to--
    . . .
    (3) . . . promote, manage, establish, carry on, or
    facilitate the promotion, management, establishment, or
    carrying on, of any unlawful activity,
    and thereafter performs or attempts to perform--
    (A) an act described in paragraph (1) or (3) shall be
    fined under this title, imprisoned not more than 5 years,
    or both . . . .
    19
    A "racketeering activity" is defined in the United States
    Code as "any act or threat" involving certain specified crimes,
    including bribery, "which is chargeable under State law and
    punishable by imprisonment for more than one year," as well as any
    act indictable under numerous federal statutory provisions,
    including the Travel Act. See 18 U.S.C. § 1961(1); see also 18
    U.S.C. § 1959(b)(1) (adopting the meaning of "racketeering
    activity" set forth in § 1961).
    -56-
    racketeering conduct that has been identified by the government is
    bribery in violation of federal and Puerto Rico laws.20    Indeed,
    count two, which alleged a substantive Travel Act violation,
    charged Bravo with traveling in interstate commerce with the intent
    to commit those two types of bribery, i.e., in violation of § 666
    and in violation of Puerto Rico law.
    On count one, the jury found Bravo guilty of conspiracy,
    but it rejected the § 666 (federal bribery) objective.    It found
    that he had conspired only to travel in interstate commerce "in aid
    of racketeering."    The jurors were not asked to specify the
    unlawful activity that was the purpose of the travel.21   However,
    20
    The Travel Act object of the conspiracy described in the
    indictment reads as follows:
    Interstate Travel in Aid of Racketeering: that is, to
    travel in interstate commerce from the Commonwealth of
    Puerto Rico to the State of Nevada, with intent to
    promote, manage, establish, carry on, and facilitate the
    promotion, management, establishment, and carrying on, of
    an unlawful activity, to wit bribery in violation of the
    laws of the United States and the Commonwealth of Puerto
    Rico, in violation of Title 18, United States Code,
    Sections 1952(a)(3)(A) and 2.
    21
    The combination of a conspiracy offense and the Travel Act
    produces unusual complexity because each requires an unlawful
    objective. The result is that, when the two crimes are charged
    together, the government must show multiple layers of predicates.
    Hence, to prove a conspiracy to violate the Travel Act, the
    government must show (1) a conspiratorial agreement (2) to travel
    (3) in aid of a specified unlawful activity. Here, the verdict
    form identified only the generic "racketeering" as the purpose of
    the Travel Act conspiracy, though it alleged two Travel Act
    objectives in the substantive count: bribery under § 666 and
    bribery under Puerto Rico law. As noted, the jury found only the
    latter.
    -57-
    on count two, the substantive Travel Act offense, the jury found
    Bravo guilty of traveling in interstate commerce with the intent to
    commit bribery in violation of Puerto Rico bribery law.         The jury
    found that he did not violate the Travel Act with the intent to
    commit § 666 bribery. Thus, in both the context of identifying the
    object of the alleged conspiracy (§ 666 bribery or Travel Act) and
    in the context of choosing the unlawful activity that was the
    target of the Travel Act (§ 666 bribery or bribery under Puerto
    Rico law), the jury rejected the allegation that Bravo's conduct
    implicated the federal bribery statute.
    Bravo moved for a judgment of acquittal on count two
    because   the   Puerto   Rico   bribery   statutes   that   provided   the
    predicate for the Travel Act violation were repealed before the Las
    Vegas trip took place.      Specifically, the laws were repealed on
    June 18, 2004, nearly one year before the trip; the repeal became
    effective on May 1, 2005, about two weeks before the trip took
    place.    Because § 1952 requires the commission of an overt act to
    promote the criminal object of the travel after the interstate
    travel takes place, see 18 U.S.C. § 1952(a), the district court
    granted Bravo's motion, concluding that "the acts that defendant
    Bravo took to fulfill the 'thereafter' requirement all occurred
    after May 1, 2005, and therefore, after section 4363 was repealed.
    Defendant Bravo cannot be convicted of conduct that was effectively
    -58-
    not a crime at the time the offense took place."                    United States v.
    Bravo-Fernandez, 
    828 F. Supp. 2d 441
    , 449 (D.P.R. 2011).22
    Bravo also moved for acquittal on the conspiracy charge,
    arguing that the conspiracy conviction -- which was based on a
    Travel Act violation -- necessarily must fall with the substantive
    Travel Act charge.          His theory was as follows: if the only target
    of   the    Travel    Act    found    by    the    jury      when   considering     the
    substantive     Travel      Act    charge    (count     two)     was   to   further   a
    violation of the Puerto Rico statutes, and that targeted activity
    was not unlawful, there could be no unlawful conspiracy to violate
    the Travel Act.           In other words, he argued that the conspiracy
    count must be dismissed because the jury verdicts rejecting § 666
    as   an    object    of   the     conspiracy      and   as   a   predicate    for   the
    substantive Travel Act charge left only the repealed Puerto Rico
    bribery laws as the crime the jury could have found as the
    racketeering activity alleged to be the target of the Travel Act
    conspiracy.     In that circumstance, there was no viable predicate
    for the Travel Act conspiracy.
    The district court denied the motion.                  It held that the
    jury could have reached different conclusions about the objective
    of Bravo's travel when separately considering the conspiracy and
    22
    Although the Commonwealth legislature enacted new bribery
    provisions to replace the repealed statutes, the government has not
    argued that the new laws provide any basis for the convictions
    here.
    -59-
    substantive Travel Act counts.      Stated otherwise, the court found
    that the jury's unelaborated finding on count one that Bravo had
    conspired to travel "in aid of racketeering" could have reflected
    a finding that Bravo had conspired to violate the Travel Act with
    the   intent   to   promote   federal   program   bribery.   The   court
    considered this outcome possible even though, when considering the
    substantive Travel Act crime (count two), the jury found that Bravo
    did not violate the Travel Act for that purpose and even though the
    jury explicitly found (on count one) that Bravo did not conspire to
    violate § 666.      The court held that any inconsistency in such a
    scenario was not problematic.
    On appeal, Bravo reiterates his argument for acquittal on
    the conspiracy charge.    He again asserts that it was impossible to
    engage in a conspiratorial agreement to travel to violate the
    Puerto Rico bribery statutes on May 13, 2005, two weeks after the
    repeal became effective and nearly a year after the legislature
    voted to repeal the statutes, because "one cannot conspire to
    commit a nonexistent crime."     In addition, he maintains that, even
    if the district court correctly ruled that he could be convicted
    for conspiring to travel in connection with a bribery that is
    unlawful under § 666 -- despite the jury's rejection of federal
    bribery as the predicate for his substantive Travel Act offense --
    the conspiracy conviction cannot stand.       The problem, he asserts,
    -60-
    is that it is impossible to tell whether the jury based its Travel
    Act conspiracy finding on the federal or Commonwealth statutes.
    The government, noting that a defendant may be convicted
    on a conspiracy charge even if he does not successfully complete
    the crime that is the object of the conspiracy, argues that the
    jury could have found that Bravo conspired to travel to violate the
    Puerto Rico bribery laws if an overt act was taken before the
    statute was repealed.   The government points out that the statute
    was still in effect when Bravo booked the hotel reservations,
    ordered the boxing tickets, and took other acts "which were in
    furtherance of the corrupt exchange."     The government interprets
    Bravo's argument to be a legal impossibility defense -- i.e., he
    could not be found guilty because it would have been impossible for
    him to commit the crime -- and states that "[c]ourts have come to
    abolish impossibility as a defense, particularly with respect to
    the crime of conspiracy."
    Having set the scene, we now proceed to consider whether
    Bravo's conspiracy conviction may stand with either § 666 or Puerto
    Rico bribery law as the Travel Act predicate.
    B. Conspiracy to Violate the Travel Act to Promote Puerto Rico
    Bribery
    Although   the    government   is   correct   that   "legal
    impossibility" is often an ineffective defense in a conspiracy case
    because a conspiracy charge does not require a completed crime,
    Bravo's argument implicates a more potent form of the doctrine. He
    -61-
    invokes what has been referred to as "pure legal impossibility,"
    which arises when no statute "proscribe[s] the result that the
    defendant expected, desired, and intended to achieve."           See Ira P.
    Robbins, Attempting the Impossible: the Emerging Consensus, 23
    Harv. J. on Legis. 377, 390 (1986); see also United States v.
    Farner, 
    251 F.3d 510
    , 513 n.2 (5th Cir. 2001); In re Sealed Case,
    
    223 F.3d 775
    , 779 (D.C. Cir. 2000).         "Pure legal impossibility is
    always a defense.     For example, a hunter cannot be convicted of
    attempting to shoot a deer if the law does not prohibit shooting
    deer in the first place."      United States v. Hsu, 
    155 F.3d 189
    , 199
    n.16 (3d Cir. 1998).    Although Hsu's hypothetical discussed pure
    legal impossibility in the context of attempts, "[o]bviously a
    charge of conspiracy to shoot a deer would be equally untenable."
    In re Sealed 
    Case, 223 F.3d at 779
    .
    The type of legal impossibility that the government cites
    has been referred to as "mixed fact/law impossibility." Such cases
    "involve a factual mistake relating to a legal determination.           In
    every case . . . a pre-existing law proscribed the actor's goal,
    thus distinguishing this category from pure legal impossibility."
    
    Robbins, supra, at 394
    .        These cases "use[] the label 'legal
    impossibility'   to    refer    to    the   impossibility   of    actually
    accomplishing the intended plot," although there is never "any
    question that if the plot had succeeded the conduct itself would be
    -62-
    criminal."   United States v. Ali, 
    561 F. Supp. 2d 265
    , 267-68
    (E.D.N.Y. 2008).
    This is a case of pure legal impossibility.     The jury
    found a conspiracy to violate the Travel Act with the intent to
    facilitate racketeering activity (either federal or state bribery).
    The evidence shows, and the indictment alleges, that the travel
    underlying the charge was to take place on a specific date to
    coincide with the boxing match between Felix Trinidad and Winky
    Wright scheduled for May 14, 2005 -- nearly two weeks after the
    repeal of the Puerto Rico bribery statutes was to go into effect.
    Thus, the jury could not have found Bravo guilty of conspiracy to
    violate the Travel Act for the purpose of aiding a violation of
    these Puerto Rico bribery laws because the alleged agreement was to
    travel at a time when Bravo's conduct could not violate those laws.
    That the plans to take the trip to Las Vegas were allegedly made
    before the statute's repeal took effect is of no significance,
    since the plans envisioned travel on a specific date -- after May
    1.   In this case, "a pre-existing statute [did] not proscribe the
    result that the defendant expected, desired, and intended to
    achieve," 
    Robbins, supra, at 390
    , because the Puerto Rico bribery
    statutes at issue would no longer "exist" when the travel was to
    take place. In short, Defendants were "conspiring" to do something
    -63-
    that would not be prohibited by these Puerto Rico bribery laws on
    the date they planned to do it.23
    An extension of the deer hunting hypothetical used in
    Hsu and In re Sealed Case illustrates this point. Assume that deer
    hunting season begins on September 1; it is against the law to hunt
    deer before September 1.   On August 15, a man and his friend visit
    a sporting goods store to purchase rifles and ammunition, intending
    to use them to hunt deer on September 2.     Are the men guilty of
    conspiring to illegally hunt deer?    They are not: although their
    planning took place during a time when it would have been illegal
    to engage in the subject activity, no statute prohibited that
    activity on the date on which they planned to engage in it.
    It therefore follows that, with respect to the Puerto
    Rico bribery basis for the alleged Travel Act violation, "since the
    conduct allegedly underlying the conspiracy was not a crime, no
    . . . conspiracy to commit that conduct can exist either."    
    Ali, 561 F. Supp. 2d at 267.24
    The government claims, however, that even
    23
    We reject the government's assertion that Bravo may not
    benefit from the repeal without demonstrating that he had notice of
    it.
    24
    In this case, it is not pertinent that, at the time Bravo
    and the others agreed to travel, the repeal of the Puerto Rico
    bribery statutes at issue had not yet gone into effect. The state
    of the law at the time of their agreement was such that, on the day
    they planned to travel, such travel would not be unlawful. Hence,
    there was no unlawful objective of their agreement, and therefore
    no basis for a conspiracy charge.
    It might be a different case if, at the time they agreed, the
    legislature had not already decided to change the state of the law
    -64-
    if the Puerto Rico bribery predicate must be struck, the jury could
    have relied on § 666 as a predicate for the conspiracy to violate
    the Travel Act.    We now turn to that possibility.
    C. Conspiracy to Violate the Travel Act to Promote Federal Bribery
    The government urges us to adopt the view taken by the
    district court, i.e., that the jury's rejection of § 666 as a
    direct   object   of   the   conspiracy   and   as   a   predicate   for    the
    substantive Travel Act violations does not negate the possibility
    that the jury could have found that the conspiracy to violate the
    Travel Act involved planning to travel to violate § 666.             The gist
    of this approach is that the jury could have found that Bravo
    conspired with others to travel for the purpose of promoting
    federal bribery, while also finding that he neither agreed with
    others directly to commit federal bribery (its finding on count
    one) nor in fact traveled to promote federal bribery (its finding
    on count two).     The government admits that such a view of the
    jury's judgments appears inconsistent, but it asserts that the
    verdicts are reconcilable and therefore permissible.                 It cites
    precedent in which inconsistent verdicts have been upheld.                 See,
    e.g., United States v. Powell, 
    469 U.S. 57
    , 69 (1984).
    effective May 1, 2005.     In other words, we do not address the
    hypothetical situation in which Bravo and his cohorts had set their
    plan in motion before the legislature acted to repeal the statutes.
    -65-
    But the problem here is not merely the possibility of
    inconsistent verdicts.    Rather, even if we were to assume that the
    jury could have relied on a § 666 theory in finding Bravo guilty on
    the Travel Act conspiracy count, we do not in fact know whether the
    racketeering activity found by the jury as a predicate was bribery
    under federal law or bribery under the repealed Puerto Rico
    statutes.    We are thus confronted with a situation in which "the
    verdict is supportable on one ground, but not on another, and it is
    impossible to tell which ground the jury selected."         Yates v.
    United States, 
    354 U.S. 298
    , 312 (1957), overruled on other grounds
    by Burks v. United States, 
    437 U.S. 1
    (1978).       "When a jury has
    been presented with several bases for conviction, one of which is
    legally erroneous, and it is impossible to tell which ground the
    jury convicted upon, the conviction cannot stand."     United States
    v. Sawyer, 
    85 F.3d 713
    , 730-31 (1st Cir. 1996); see also United
    States v. Mubayyid, 
    658 F.3d 35
    , 71 (1st Cir. 2011); United States
    v. Kavazanjian, 
    623 F.2d 730
    , 739-40 (1st Cir. 1980) (reversing
    verdict on multi-object conspiracy conviction under § 371 where one
    object failed to state a crime).        We therefore conclude that
    Bravo's conspiracy conviction cannot be upheld.
    But our inquiry does not end here.   The question remains
    whether the judgment entered on count one as to Bravo must be
    reversed or whether it should be vacated and the case remanded for
    further proceedings.     Generally, when we find that a conviction
    -66-
    cannot stand because the jury may have convicted upon a legally
    invalid basis, we will remand for a new trial, provided that there
    is sufficient evidence to support a conviction on a valid basis (or
    bases).   See United States v. Pendergraft, 
    297 F.3d 1198
    , 1210
    (11th Cir. 2002); 
    Kavazanjian, 623 F.2d at 739
    .     The government
    argues for that course here.    It maintains that the evidence was
    sufficient for the jury to find that Bravo conspired to travel in
    interstate commerce to violate § 666 and, hence, he should be
    retried on count one.
    We disagree.     Regardless of the sufficiency of the
    evidence, retrial on the conspiracy count is barred by the Double
    Jeopardy Clause.25   While the Double Jeopardy Clause is widely
    understood to bar retrial on a charge on which a defendant was
    previously acquitted, Yeager v. United States, 
    557 U.S. 110
    , 117-18
    (2009), it also "precludes the Government from relitigating any
    issue that was necessarily decided by a jury's acquittal in a prior
    trial," 
    id. at 119 (emphasis
    added); see also Ashe v. Swenson, 
    397 U.S. 436
    , 443-44 (1970); United States v. Orrego-Martinez, 
    575 F.3d 1
    , 6 (1st Cir. 2009).    This is known as the "issue preclusion" or
    "collateral estoppel" prong of the Double Jeopardy Clause.   United
    States v. Coughlin, 
    610 F.3d 89
    , 95 (D.C. Cir. 2010); United States
    v. Wittig, 
    575 F.3d 1
    085, 1095 (10th Cir. 2009).    In determining
    25
    Although Bravo did not formally label his challenge to the
    conspiracy conviction as a double jeopardy challenge, the logical
    conclusion of his argument is exactly that.
    -67-
    what was "necessarily decided" for purposes of issue preclusion,
    the Supreme Court has recently reaffirmed that "courts should
    'examine the record of a prior proceeding, taking into account the
    pleadings,      evidence,     charge,      and    other    relevant     matter,      and
    conclude whether a rational jury could have grounded its verdict
    upon   an   issue     other   than    that   which    the      defendant     seeks   to
    foreclose      from   consideration.'"           
    Yeager, 557 U.S. at 119-20
    (quoting 
    Ashe, 397 U.S. at 444
    ).                 The Court has made clear that
    this "inquiry 'must be set in a practical frame and viewed with an
    eye to all the circumstances of the proceedings,'" id. (quoting
    
    Ashe, 397 U.S. at 444
    ), and that "the rule of collateral estoppel
    in criminal cases is not to be applied with the hypertechnical and
    archaic approach of a 19th century pleading book, but with realism
    and rationality," 
    Ashe, 397 U.S. at 444
    .
    Here, the jury's verdict on count one did not expressly
    acquit Bravo on a Travel Act conspiracy whose purpose was to
    promote § 666 bribery.         The verdict form for count one asked the
    jury to answer "yes" or "no" only as to whether Bravo had conspired
    to violate the Travel Act "in aid of racketeering," without
    specifying any racketeering activity.                 However, federal program
    bribery in violation of § 666 was one of the two racketeering
    crimes alleged in the indictment and argued by the government --
    the    other    being   bribery      in   violation       of   Puerto   Rico     law.
    Significantly, the jury did render a conspiracy judgment with
    -68-
    respect to § 666, rejecting federal bribery as a direct object of
    the   conspiracy.     The   pertinent      question,     then,   is   this:   by
    unambiguously stating on the verdict form that Bravo did not
    conspire to violate § 666, did the jury also "necessarily decide"
    that he did not conspire to travel for the purpose of violating
    § 666? Taking a practical, realistic approach to this question, we
    must answer it in the affirmative.
    First, we find it difficult to fathom how the jury could
    have found that Bravo conspired to travel for the purpose of
    violating § 666 without also finding that he conspired to violate
    § 666.    The jury's explicit rejection of the allegation that Bravo
    conspired to violate § 666 is strong evidence that the jury did not
    find federal program bribery to be the racketeering activity
    underlying the Travel Act conspiracy.               Cf.    United States      v.
    Cabrera, 
    804 F. Supp. 2d 1261
    , 1267-70 (M.D. Fla. 2011).               Second,
    the jury found on count two -- the substantive Travel Act count --
    that Bravo was guilty only of traveling with the intent to commit
    bribery    in   violation   of   Puerto    Rico   law.     Again,     the   jury
    explicitly rejected allegations that either the conspiracy or the
    Travel Act conduct implicated § 666.
    Given these other § 666 judgments by the jury, we
    conclude that its verdict on the Travel Act conspiracy can only
    rationally be understood as a finding that Bravo conspired to
    travel to Las Vegas in mid-May 2005 for the purpose of promoting
    -69-
    Puerto Rico bribery.   We will not bend over backwards to formulate
    some route by which the jury could have conceivably found that
    § 666 was the predicate of the Travel Act conspiracy when any
    reasonable assessment of the verdict shows that no such road was
    taken.   We therefore conclude that re-prosecuting Bravo on count
    one would violate the Double Jeopardy Clause.
    VI.
    Martínez also challenges his conspiracy conviction.    As
    we shall explain, although the circumstances are different from
    Bravo's, the outcome is the same.
    A. Background
    The jury indicated that it unanimously found Martínez
    guilty of conspiracy on count one.    The verdict form listed three
    potential objects of the conspiracy, and the jury was instructed to
    "check all that you unanimously find to apply."   The jury checked
    "No" as to each of the three identified objects of the conspiracy.
    In other words, although the jury was unanimous in finding that
    Martínez was guilty of conspiring to do something illegal, they
    were not unanimous in their view of what that illegality was.
    Immediately after the verdict was read by the courtroom
    deputy, Martínez's attorney, Mr. Lowell, asked the court to strike
    the verdict on count one, stating: "As to Hector Martínez, they
    found 'no' for all the particulars, so, consequently, this is an
    impossibility."   The court and the government were uncertain about
    -70-
    the proper course.      Lowell, however, remained steadfast, asserting
    that "as to Count 1, by law, you have to enter the verdict of not
    guilty as to Count 1 as to Mr. Martínez."
    Lowell then asked the court to poll the jury individually
    as to count five, the substantive federal bribery count.                The
    government recommended that the court simply take a general poll.
    Bravo's attorney, Mr. Chesnoff, asked that the jury be polled
    individually "as to every count and every specification," stating
    that "[y]ou have a jury that has obviously been confused about its
    verdict."   The court rejected both defense attorneys' requests and
    conducted only a general poll, asking each juror if the verdict
    announced by the courtroom deputy was his or her verdict.              This
    approach did not clarify the issue with the conspiracy verdict as
    to Martínez.
    After the jury was polled, the court asked if there were
    any motions by the defense.            Attorney Lowell reiterated his
    contention that "the Court must vacate Count 1."                  The court
    responded: "All right.      Well, let me discharge the jury, and well
    -- we'll deal with those legal matters later."               The jury was
    escorted from the courtroom, and Lowell again stated that the
    jury's   verdict   on   Martínez's    conspiracy   charge   was   "a   legal
    impossibility," and "that being the case, the Court must strike
    that guilty verdict.       There's no alternative."         The government
    pushed back, asking the court for time to brief the issue before it
    -71-
    made its decision.       After some further back and forth, the court
    stated: "I agree with Mr. Lowell.            Count 1 as far as Defendant
    Martínez is dismissed."           The discussion then shifted to other
    matters.
    In a short order issued the next day, the court sua
    sponte "reinstated" Martínez's conviction on count one "without
    prejudice of the parties having a full opportunity to brief the
    issues discussed in open court."          Martínez filed an eighteen-page
    brief three days later, stating that the court's change of course
    was "beyond surprising" and insisting that the further proceedings
    ordered by the court "are an affront to the Fifth Amendment's Due
    Process and Double Jeopardy Clauses, and the Sixth Amendment's
    right to trial by jury."         He argued that "[a]lthough the statutory
    basis for Mr. Lowell's motion and this Court's decision was not
    cited, it was plainly a motion made and a judgment rendered under
    [Federal]   Rule   [of    Criminal    Procedure]      29,"   and    that   double
    jeopardy    therefore      attached.          The     government      filed     a
    "non-opposition"     to    Martínez's        motion    shortly      thereafter,
    indicating that "the Court should dismiss defendant Martínez's
    guilty   verdict   on    Count    One."      The    next   day,    however,   the
    government filed a supplemental response, arguing that, at most,
    Martínez would be entitled to a mistrial pursuant to Federal Rule
    of Criminal Procedure 33 on count one and a dismissal without
    prejudice, not a Rule 29 dismissal based on insufficiency of the
    -72-
    evidence.   Martínez replied that the dismissal sought and granted
    was a dismissal pursuant to Rule 29, that the dismissal was
    properly granted, and that the court's decision could not be
    withdrawn or relitigated, as jeopardy attached to it.
    On August 30, 2011, the district court issued an order
    stating that the initial dismissal did not preclude a mistrial. The
    court stated that because it did not explicitly make a finding that
    the evidence was insufficient to sustain the conviction, Rule 29
    was not implicated.        Instead, it maintained that "the Court
    'dismissed' [the] verdict based on defense counsel's claim of
    'legal impossibility.'"      Moreover, the court stated that even if
    its actions fell within the scope of Rule 29, the Double Jeopardy
    Clause permits a prosecution appeal to reinstate a jury's guilty
    verdict that a judge subsequently discarded.
    B. Legal Principles
    The Fifth Amendment states that no person shall "be
    subject for the same offence to be twice put in jeopardy of life or
    limb."   U.S. Const. amend. V.    The Double Jeopardy Clause "shields
    a defendant from a second prosecution for the same offense after
    either conviction or acquittal."      United States v. Morris, 
    99 F.3d 476
    , 478 (1st Cir. 1996).        In determining whether the Double
    Jeopardy Clause has been violated, "a reviewing court first must
    ask   whether   jeopardy   attached   in   the   original   [trial]   court
    proceeding." United States v. Pacheco, 
    434 F.3d 106
    , 112 (1st Cir.
    -73-
    2006)    (alteration   in   original)      (citation   omitted)    (internal
    quotation marks omitted).
    "Perhaps the most fundamental rule in the history of
    double   jeopardy   jurisprudence    has    been   that   '[a]    verdict   of
    acquittal . . . could not be reviewed, on error or otherwise,
    without putting [a defendant] twice in jeopardy, and thereby
    violating the Constitution.'" United States v. Martin Linen Supply
    Co., 
    430 U.S. 564
    , 571 (1977) (alteration in original) (quoting
    United States v. Ball, 
    163 U.S. 662
    , 671 (1896)).                    We have
    previously held that "[i]t is beyond cavil that, for double
    jeopardy purposes, the finality accorded to jury verdicts of
    acquittal extends equally to judicially rendered judgments of
    acquittal." 
    Pacheco, 434 F.3d at 112
    . It is therefore critical to
    determine whether the district court's statement that "Count 1 as
    far as Defendant Martínez is dismissed" constitutes a judgment of
    acquittal.
    The Supreme Court has repeatedly "emphasized that what
    constitutes an 'acquittal' is not to be controlled by the form of
    the judge's action."        Martin 
    Linen, 430 U.S. at 571
    ; see also
    United States v. Scott, 
    437 U.S. 82
    , 96 (1978); United States v.
    Sisson, 
    399 U.S. 267
    , 290 (1970). Instead, a reviewing court "must
    determine whether the ruling of the judge, whatever its label,
    actually represents a resolution, correct or not, of some or all of
    the factual elements of the offense charged."             Martin Linen, 430
    -74-
    U.S. at 571; see also 
    Pacheco, 434 F.3d at 112
    .    That the district
    court did not explicitly invoke Rule 29 in "dismissing" count one,
    then, is not dispositive on the issue of whether its actions
    constituted an acquittal. Cf. United States v. Jorn, 
    400 U.S. 470
    ,
    478 n.7 (1971) ("[T]he trial judge's characterization of his own
    action cannot control the classification of the action for the
    purposes of our appellate jurisdiction.").
    The difficulty in this case is that the district court's
    assessment of the conspiracy charge as to Martínez does not
    directly engage with the facts presented at trial.    Instead of the
    normal inquiry into factual sufficiency, the court's determination
    that the conspiracy count must be "dismissed" appears to be based
    on a legal conclusion regarding the requirements of a conspiracy
    conviction under 18 U.S.C. § 371 -- specifically, that if the jury
    cannot reach an agreement as to the object of a conspiracy, the
    conviction cannot stand as a matter of law.       The Supreme Court,
    however, has not limited acquittals for double jeopardy purposes to
    cases involving factual assessments of the evidence presented to
    the jury.    In several cases, including one decided earlier this
    year, the Supreme Court has held that legal determinations by the
    court can create a double jeopardy bar to retrial.
    In Arizona v. Rumsey, an Arizona trial judge conducted a
    sentencing hearing to determine whether a defendant convicted of
    armed robbery and first degree murder was eligible for the death
    -75-
    penalty.    
    467 U.S. 203
    , 205 (1984).               The trial judge mistakenly
    held that Arizona's statutory aggravating factor covering killings
    for   pecuniary   gain    was    limited       to   "a   contract-type   killing
    situation and not robbery, burglary, etc."               
    Id. at 206 (quotation
    marks   omitted).        The    judge    therefore       found   no   aggravating
    circumstances and sentenced the defendant to life imprisonment.
    
    Id. The State successfully
    appealed to the Supreme Court of
    Arizona and obtained a death sentence on remand under the proper
    standard.    
    Id. at 207-08. The
    U.S. Supreme Court found that the
    retrial on the penalty phase issue was a double jeopardy violation,
    because the trial judge's original "judgment, based on findings
    sufficient to establish legal entitlement to the life sentence,
    amounts to an acquittal on the merits and, as such, bars any
    retrial of the appropriateness of the death penalty." 
    Id. at 211. It
    continued:
    In making its findings, the trial court relied
    on a misconstruction of the statute defining
    the pecuniary gain aggravating circumstance.
    Reliance on an error of law, however, does not
    change the double jeopardy effects of a
    judgment that amounts to an acquittal on the
    merits.   "[T]he fact that the acquittal may
    result from erroneous evidentiary rulings or
    erroneous interpretations of governing legal
    principles . . . affects the accuracy of that
    determination, but it does not alter its
    essential character."
    
    Id. (quoting United States
    v. Scott, 
    437 U.S. 82
    , 98 (1978))
    (emphasis added) (internal quotation marks omitted).
    -76-
    Just two years after Rumsey, the Court considered another
    case in which a judge's "legal determination" was at issue.           In
    Smalis v. Pennsylvania, the Supreme Court of Pennsylvania held that
    a demurrer, which requires the court to determine "whether the
    evidence, if credited by the jury, is legally sufficient to warrant
    the conclusion that the defendant is guilty beyond a reasonable
    doubt," does not involve a factual determination, but rather
    "purely one of law," and is therefore not the equivalent of an
    acquittal for double jeopardy purposes.     
    476 U.S. 140
    , 143 (1986)
    (internal   quotation   marks   omitted).   The   U.S.   Supreme   Court
    reversed in a brief opinion, stating that "[w]hat the demurring
    defendant seeks is a ruling that as a matter of law the State's
    evidence is insufficient to establish his factual guilt," which
    constitutes an acquittal under the Double Jeopardy Clause.         
    Id. at 144. The
    Court recently reaffirmed its positions in Rumsey and
    Smalis in Evans v. Michigan, 
    133 S. Ct. 1069
    (2013).      In Evans, the
    Supreme Court considered "whether retrial is barred when a trial
    court grants an acquittal because the prosecution had failed to
    prove an 'element' of the offense that, in actuality, it did not
    have to prove."   
    Id. at 1074. The
    Court found that, in substance,
    the issue was no different than the one presented in Rumsey: it
    "involve[d] an antecedent legal error that led to an acquittal
    because the State failed to prove some fact it was not actually
    -77-
    required to prove."   
    Id. at 1076. The
    fact that Evans involved the
    addition of a nonessential element, while Rumsey involved only the
    misinterpretation of an essential element, was of no moment to the
    Court. 
    Id. at 1076-77. The
    Court held that the trial court's
    "judgment, however erroneous it was, precludes reprosecution." 
    Id. at 1078 (internal
    quotation marks omitted).
    C. Application
    With these decisions in mind, we have little difficulty
    concluding that the district court's "dismissal" of the conspiracy
    count against Martínez was an acquittal.    Rightly or wrongly,26 the
    court agreed with Lowell's assertions that a conspiracy with no
    object was "a legal impossibility," and that the jury's verdict
    must be "struck" and the count "dismissed."       In so finding, the
    court made a determination as to the legal requirements necessary
    for a conspiracy conviction under § 371 and concluded that the jury
    had found the evidence insufficient to meet those requirements.27
    26
    Because the correctness of the district court's decision on
    this issue is irrelevant, we choose not to address it, other than
    to note that there appears to be no case law directly on point.
    Martínez relies primarily upon an out-of-circuit district court
    case involving facts that differ materially from the present case,
    United States v. Lucarelli, 
    490 F. Supp. 2d 295
    (D. Conn. 2007),
    while the government cites to an Eighth Circuit case that involved
    a special verdict form in a bankruptcy fraud case, United States v.
    Mitchell, 
    476 F.3d 539
    (8th Cir. 2007).       Neither offers clear
    guidance.
    27
    Although double jeopardy cases in which courts order an
    acquittal based on the sufficiency of the evidence ordinarily
    involve the court's assessment of the evidence itself, the
    principles are equally applicable in this somewhat different
    -78-
    For our purposes, it does not matter if this interpretation of
    § 371 added "an 'element' of the offense that, in actuality, [the
    government] did not have to prove," 
    id. at 1074; misconstrued
    the
    actual elements of the statute, 
    Rumsey, 467 U.S. at 211
    ; or
    faithfully adhered to the statute's requirements. All that matters
    is   that   the   district   court   made   "a   determination   that   the
    [government] had failed to prove its case."         
    Evans, 133 S. Ct. at 1075
    .
    One issue remains for our consideration.      In declaring a
    mistrial, the district court found that even if the initial
    "dismissal" could be considered a judgment of acquittal, the Double
    Jeopardy Clause would not prevent an appeal by the government to
    reinstate the jury's original guilty verdict.         In support of this
    proposition, the court cited Smith v. Massachusetts, which states:
    Our cases have made a single exception to the
    principle that acquittal by judge precludes
    reexamination of guilt no less than acquittal
    by jury: When a jury returns a verdict of
    guilty and a trial judge (or an appellate
    court) sets aside that verdict and enters a
    judgment of acquittal, the Double Jeopardy
    Clause does not preclude a prosecution appeal
    to reinstate the jury verdict of guilty.
    context. Here, the court determined that the jury had functionally
    acquitted Martínez on the conspiracy count. See 
    Evans, 133 S. Ct. at 1075
    ("[A]n 'acquittal' includes a ruling by the court that the
    evidence is insufficient to convict, a factual finding [that]
    necessarily establish[es] the criminal defendant's lack of criminal
    culpability, and any other rulin[g] which relate[s] to the ultimate
    question of guilt or innocence." (alterations in original)
    (emphasis added) (citations omitted) (internal quotation marks
    omitted)).
    -79-
    
    543 U.S. 462
    , 467 (2005).      Although at first blush this principle,
    first announced in United States v. Wilson, 
    420 U.S. 332
    , 352-53
    (1975), seems potentially applicable to the present case, it is
    not.
    As the Court noted in Rumsey, "[n]o double jeopardy
    problem was presented in Wilson because the appellate court, upon
    reviewing asserted legal errors of the trial judge, could simply
    order the jury's guilty verdict reinstated; no new factfinding
    would be necessary, and the defendant therefore would not be twice
    placed in 
    jeopardy." 467 U.S. at 211-12
    .        The Rumsey Court found
    that the Wilson exception was inapplicable to that case, because
    "[w]hereas the defendant in Wilson was not to be subjected to a
    second trial after an acquittal at his first, that is precisely
    what . . . happened" to Rumsey.          The Court has made clear that the
    Wilson exception does not violate the Double Jeopardy Clause
    precisely because allowing appeal in those circumstances does not
    subject a defendant "to further factfinding proceedings going to
    guilt or innocence" following an acquittal. 
    Smith, 543 U.S. at 467
    (internal quotation marks omitted); see also 
    Smalis, 476 U.S. at 145
    ("[S]ubjecting the defendant to postacquittal factfinding
    proceedings   going   to    guilt   or    innocence    violates   the   Double
    Jeopardy Clause.").
    Here, the government presumably requested a dismissal
    without   prejudice    of    Martínez's     conviction    so   that     it   can
    -80-
    reprosecute him under § 371.        If we were to allow the district
    court to recast its acquittal as a mistrial, the government would
    get   another   opportunity   to   subject   Martínez   to   "factfinding
    proceedings going to guilt or innocence," hoping this time for a
    less ambiguous result.        That would be a classic instance of
    impermissible double jeopardy. Because the court's "dismissal" was
    an acquittal for double jeopardy purposes, and because the Wilson
    exception does not apply, the decision cannot be reconsidered. See
    
    Smith, 543 U.S. at 470-73
    .
    VII.
    For the foregoing reasons, we reverse Bravo's conspiracy
    conviction, and reverse the district court's order declaring a
    mistrial as to Martínez's conspiracy count. We direct the district
    court to enter a judgment of acquittal on both charges.         We vacate
    Martínez's and Bravo's § 666 convictions and remand for further
    proceedings consistent with this opinion.
    – Concurring Opinion Follows –
    -81-
    HOWARD, Circuit Judge, concurring in part and concurring
    in the judgment.       I join the court's judgment, although on one
    issue I would reach the same result by a different route.                   The
    majority concludes, as a matter of law, that Section 666 does not
    criminalize gratuities.        I believe that the statute is unclear
    enough   that    the   rule    of   lenity    precludes    the    defendants'
    convictions     to   the   extent   that   they   could   have   rested    on   a
    gratuity.    While the majority does an admirable job of explaining
    its reasoning, other considerations give me pause.
    First, the Supreme Court has stated that "[a]n illegal
    gratuity . . . may constitute merely a reward for some future act
    that the public official will take (and may already have determined
    to take), or for a past act that he has already taken."                   United
    States v. Sun-Diamond Growers of Cal., 
    526 U.S. 398
    , 405 (1999)
    (emphasis added).      Thus, a "reward" can be a payment that does not
    influence an official's actions, a reading that the majority
    rejects when interpreting Section 666.            Although the Court was not
    interpreting Section 666 or defining the word "reward," it was
    interpreting Section 201, a closely related statute.                 Thus, I
    hesitate to conclude that the meaning of "reward" as used in
    Section 666 is at odds with the Court's use of that word.
    Second, a problem arises if we read the bribery provision
    of Section 201(b) to prohibit the same conduct as Section 666.
    Section 201(b) prohibits giving or receiving anything of value with
    -82-
    the intent to "influence" or of "being influenced."                           18 U.S.C.
    § 201(b)(1)(A), (b)(2)(A).               Section 666, by contrast, prohibits
    giving or receiving anything of value with the intent to "influence
    or reward" or "to be influenced or rewarded."                     
    Id. § 666(a)(2), (a)(1)(B).
         If the scope of these prohibitions is the same, then
    the word "reward" has no independent meaning in Section 666, which
    would seem to violate the requirement that we are to give effect to
    every word of a statute.           See Ransom v. FIA Card Servs., N.A., 
    131 S. Ct. 716
    , 724 (2011).             I am not sure that this problem can be
    resolved by reading "reward" as clarifying how a bribe can be
    timed, as the majority does.
    Third,     Appendix    A    to    the    United    States      Sentencing
    Guidelines     Manual     provides       that    Section     2C1.2,    the    guideline
    covering gratuities, applies to both Section 666(a)(1)(B) and
    Section 666(a)(2).          Although the Sentencing Commission cannot
    change the meaning of a statute, Congress does have the opportunity
    to review proposed guidelines before they become effective.
    28   U.S.C.    §   994(p).28       Moreover,      we    have    held   that    "Chevron
    deference     is   the    proper     criterion        for   determining      whether   a
    guideline (or, for that matter, commentary that suggests how a
    28
    Like the majority, I am concerned with the disparity between
    the statutory maximum sentences for an illegal gratuity under
    Section 201 and for a violation of Section 666. But I would point
    out that an illegal gratuity carries a base offense level three
    levels lower than bribery does, U.S. Sentencing Guidelines Manual
    §§ 2C1.1(a), 2C1.2(a) (2012).
    -83-
    guideline should be read) contravenes a statute." United States v.
    LaBonte, 
    70 F.3d 1396
    , 1404 (1st Cir. 1995), rev'd on other
    grounds, 
    520 U.S. 751
    (1997).29            While I do not suggest that
    LaBonte's    rule   applies      here,     the    Sentencing     Commission's
    determination that the gratuity guideline applies to Section 666
    does at least give me pause as to Congress's meaning.
    In the end, I would apply the rule of lenity because it
    is ambiguous whether Section 666 criminalizes gratuities.                    "The
    rule of lenity requires ambiguous criminal laws to be interpreted
    in favor of the defendants subjected to them."             United States v.
    Santos, 
    553 U.S. 507
    , 514 (2008) (plurality opinion). We apply the
    rule of lenity "only if, after seizing everything from which aid
    can be derived, we can make no more than a guess as to what
    Congress    intended."    Reno    v.     Koray,   
    515 U.S. 50
    ,   65    (1995)
    (citations omitted) (internal quotation marks omitted).                   Here, I
    can make no more than a guess as to what Congress intended
    Section 666 to mean.     Therefore, I would hold that the defendants
    cannot be convicted for giving or receiving a gratuity.
    29
    When the Supreme Court decided United States v. LaBonte, the
    three dissenting justices stated that Chevron deference was
    
    appropriate, 520 U.S. at 777
    (Breyer, J., dissenting), while the
    remaining justices chose not to decide the issue, 
    id. at 762 n.6.
    -84-
    

Document Info

Docket Number: 12-1289, 12-1290

Citation Numbers: 722 F.3d 1

Judges: Howard, Lipez, Thompson

Filed Date: 6/26/2013

Precedential Status: Precedential

Modified Date: 8/6/2023

Authorities (82)

United States v. Spector , 55 F.3d 22 ( 1995 )

United States v. Morris , 99 F.3d 476 ( 1996 )

Sony BMG Music Entertainment v. Tenenbaum , 660 F.3d 487 ( 2011 )

United States v. Edward Kavazanjian, United States of ... , 623 F.2d 730 ( 1980 )

United States v. Rodríguez-Vélez , 597 F.3d 32 ( 2010 )

United States v. Munoz-Franco , 487 F.3d 25 ( 2007 )

United States v. Lachman , 387 F.3d 42 ( 2004 )

United States v. Pacheco , 434 F.3d 106 ( 2006 )

United States v. Councilman , 418 F.3d 67 ( 2005 )

United States v. Orrego-Martinez , 575 F.3d 1 ( 2009 )

united-states-v-george-labonte-united-states-of-america-v-david-e , 70 F.3d 1396 ( 1995 )

Uphoff Figueroa v. Alejandro , 597 F.3d 423 ( 2010 )

Jay A. Pritzker v. Bob Yari , 42 F.3d 53 ( 1994 )

United States v. Sawyer , 85 F.3d 713 ( 1996 )

United States v. McNair , 605 F.3d 1152 ( 2010 )

United States v. Abel A. Mariano, Jr., United States of ... , 983 F.2d 1150 ( 1993 )

United States v. Robert C. Lahue, Doing Business as Robert ... , 170 F.3d 1026 ( 1999 )

United States v. Jimenez , 507 F.3d 13 ( 2007 )

United States v. Mubayyid , 658 F.3d 35 ( 2011 )

United States v. Wittig , 575 F.3d 1085 ( 2009 )

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