Odebrecht Construction, Inc. v. Secretary, Florida Department of Transportation , 715 F.3d 1268 ( 2013 )


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  •                 Case: 12-13958        Date Filed: 05/06/2013       Page: 1 of 44
    [PUBLISH]
    IN THE UNITED STATES COURT OF APPEALS
    FOR THE ELEVENTH CIRCUIT
    ________________________
    No. 12-13958
    ________________________
    D.C. Docket No. 1:12-cv-22072-KMM
    ODEBRECHT CONSTRUCTION, INC.,
    a Florida corporation,
    Plaintiff - Appellee,
    versus
    SECRETARY, FLORIDA DEPARTMENT
    OF TRANSPORTATION,
    Defendant - Appellant.
    ________________________
    Appeal from the United States District Court
    for the Southern District of Florida
    ________________________
    (May 6, 2013)
    Before MARCUS, HILL and SILER, * Circuit Judges:
    MARCUS, Circuit Judge:
    *
    Honorable Eugene E. Siler, Jr., United States Circuit Judge for the Sixth Circuit, sitting by
    designation.
    Case: 12-13958    Date Filed: 05/06/2013    Page: 2 of 44
    In this interlocutory appeal, the Secretary of the Florida Department of
    Transportation appeals the district court’s order granting Odebrecht Construction,
    Inc. a preliminary injunction barring the Department’s enforcement of a Florida
    law known as the “Cuba Amendment,” 
    2012 Fla. Laws 196
    , § 2 (amending 
    Fla. Stat. § 287.135
    ). Broadly speaking, the law prevents any company that does
    business in Cuba -- or that is in any way related to a company that does business in
    Cuba -- from bidding on state or local public contracts in the State of Florida. See
    
    Fla. Stat. § 287.135
    (2) (“A company that . . . is engaged in business operations in
    Cuba . . . is ineligible for, and may not bid on, submit a proposal for, or enter into
    or renew a contract with an agency or local governmental entity for goods or
    services of $1 million or more.”); 
    id.
     § 215.473(1)(c) (defining the term
    “company” to encompass all subsidiaries, parent companies, or affiliates of the
    entity).
    In a thorough opinion, the district court concluded that Odebrecht had met
    its burden of persuasion on all four elements of the preliminary injunction inquiry,
    and issued a preliminary injunction prohibiting the Florida Department of
    Transportation from implementing or enforcing the Cuba Amendment.               After
    careful review, we conclude that Odebrecht has demonstrated a substantial
    likelihood of success on its claim that the Cuba Amendment violates the
    Supremacy Clause of the Constitution under principles of conflict preemption.
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    The Cuba Amendment conflicts directly with the extensive and highly calibrated
    federal regime of sanctions against Cuba promulgated by the legislative and
    executive branches over almost fifty years.        The Supremacy Clause of the
    Constitution “provides a clear rule that federal law ‘shall be the supreme Law of
    the Land.’” Arizona v. United States, 
    132 S. Ct. 2492
    , 2500 (2012) (quoting U.S.
    Const. art. VI, cl. 2). The Cuba Amendment differs dramatically from the federal
    regime as to the entities covered, the actions triggering sanctions, and the penalties
    imposed. The Amendment also overrides the nuances of the federal law and
    weakens the President’s ability “to speak for the Nation with one voice in dealing”
    with Cuba. Crosby v. Nat’l Foreign Trade Council, 
    530 U.S. 363
    , 381 (2000). In
    addition, Odebrecht has demonstrated the other equitable requirements that warrant
    a preliminary injunction: Odebrecht would have suffered irreparable harm absent
    the injunction, the balance of harms strongly favored the injunction, and the
    injunction did not disserve the public interest. We affirm.
    I.
    Odebrecht Construction, Inc. (“Odebrecht” or “OCI”) is a Florida
    construction corporation founded in 1990, with its principal place of business in
    Coral Gables, Florida. Since its inception, Odebrecht has been awarded 35 public
    contracts in Florida worth almost $4 billion. In 2011, 100% of OCI’s revenue,
    approximately $215 million, was derived from public infrastructure and
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    transportation projects. Odebrecht continues to bid successfully on high-value
    public contracts in Florida. Thus, for instance, in May 2012, Broward County
    awarded an Odebrecht joint venture a $226 million infrastructure contract at the
    Fort Lauderdale-Hollywood International Airport.
    As for the Florida Department of Transportation (“FDOT”) in particular,
    Odebrecht has completed multiple contracts for the agency in the past with a
    combined value of around $170 million. Indeed, in June 2012, FDOT certified
    Odebrecht as qualified to bid on a number of potential FDOT contracts, with a
    maximum capacity of $1.8 billion. And Odebrecht has signaled its intent to bid on
    five different FDOT contracts through the first quarter of 2013.          In short,
    Odebrecht is not merely a speculative participant in Florida’s public contracting
    market; it is a frequent and active one.
    Odebrecht does not do business in Cuba, and has never done so.
    Odebrecht’s Brazilian parent company, Odebrecht S.A., has a different chain of
    foreign subsidiaries unrelated to Odebrecht, however, and some of those foreign
    companies do business in Cuba. More specifically, Odebrecht S.A. has a Brazilian
    subsidiary, Companhia de desenvolvimento e Participacoes, S.A., which has
    another Brazilian subsidiary, Companhia de Obras e Infra-Estrutura, which has a
    British Virgin Islands subsidiary, COI Overseas Ltd. Both Companhia de Obras e
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    Infra-Estrutura and COI Overseas Ltd. are involved in the Brazilian-financed
    expansion of the Port of Mariel in Cuba.
    The Cuba Amendment has an effective date of July 1, 2012. On June 4,
    2012, before the statute went into effect, Odebrecht filed a complaint in the U.S.
    District Court for the Southern District of Florida, seeking declaratory and
    injunctive relief barring the Secretary of the Florida Department of Transportation
    from enforcing the Cuba Amendment. The following day, Odebrecht filed its
    operative amended complaint and a motion for a preliminary injunction.
    Odebrecht claimed that the Cuba Amendment violates the Supremacy Clause, U.S.
    Const. art. VI, cl. 2; the Foreign Affairs Power, see, e.g., Zschernig v. Miller, 
    389 U.S. 429
     (1968); and the Foreign Commerce Clause, U.S. Const. art. I, § 8, cl. 3.
    After full briefing and after conducting a thorough hearing, the district court
    granted the injunction. The court reviewed at length both the Cuba Amendment
    and the federal laws relating to Cuba, and then addressed Odebrecht’s
    constitutional claims, concluding that Odebrecht had demonstrated a substantial
    likelihood of success on each of them. The court also found that Odebrecht had
    satisfied the other equitable requirements for a preliminary injunction.
    II.
    We review a district court’s grant of a preliminary injunction for abuse of
    discretion. SEC v. Unique Fin. Concepts, Inc., 
    196 F.3d 1195
    , 1198 (11th Cir.
    5
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    1999). “[B]ut we review de novo the legal conclusions on which [preliminary
    injunctions] are based.” ACLU of Fla., Inc. v. Miami-Dade Cnty. Sch. Bd., 
    557 F.3d 1177
    , 1198 (11th Cir. 2009). We review any factual findings by the district
    court for clear error. Unique Fin. Concepts, 
    196 F.3d at 1198
    .
    Under the familiar four-part test, a preliminary injunction is warranted if the
    movant demonstrates “(1) a substantial likelihood of success on the merits of the
    underlying case, (2) the movant will suffer irreparable harm in the absence of an
    injunction, (3) the harm suffered by the movant in the absence of an injunction
    would exceed the harm suffered by the opposing party if the injunction is issued,
    and (4) an injunction would not disserve the public interest.” Grizzle v. Kemp, 
    634 F.3d 1314
    , 1320 (11th Cir. 2011) (quoting N. Am. Med. Corp. v. Axiom
    Worldwide, Inc., 
    522 F.3d 1211
    , 1217 (11th Cir. 2008)). Here, as in so many
    cases, the first question is critical. We begin -- and end -- our answer to that
    question with Odebrecht’s claim that the Cuba Amendment is preempted by the
    long-standing and extensive federal regime limiting American companies from
    doing business in Cuba.
    A.
    The Supremacy Clause of the United States Constitution provides that the
    Constitution and the laws of the United States “shall be the supreme Law of the
    Land.” U.S. Const. art. VI, cl. 2. “Under this principle, Congress has the power to
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    preempt state law.” Arizona v. United States, 
    132 S. Ct. 2492
    , 2500 (2012) (citing
    Crosby v. Nat’l Foreign Trade Council, 
    530 U.S. 363
    , 372 (2000)). Preemption
    can occur in a number of circumstances. Its most straightforward form, express
    preemption occurs when Congress “enact[s] a statute containing an express
    preemption provision.” Id. at 2500-01. That has not occurred in this case, nor is
    there any claim that it has. The second -- field preemption -- precludes the states
    “from regulating conduct in a field that Congress, acting within its proper
    authority, has determined must be regulated by its exclusive governance.” Id. at
    2501 (citing Gade v. Nat’l Solid Wastes Mgmt. Ass’n, 
    505 U.S. 88
    , 115 (1992)).
    The Supreme Court has instructed us that we may infer congressional intent to
    displace state law altogether “from a framework of regulation so pervasive that
    Congress left no room for the States to supplement it or where there is a federal
    interest so dominant that the federal system will be assumed to preclude
    enforcement of state laws on the same subject.” 
    Id.
     (internal quotation marks and
    alterations omitted).
    Third, and most critical for our purposes, “state laws are preempted when
    they conflict with federal law.” 
    Id.
     (citing Crosby, 
    530 U.S. at 372
    ). Conflict
    preemption covers “cases where ‘compliance with both federal and state
    regulations is a physical impossibility.’”   
    Id.
     (quoting Fla. Lime & Avocado
    Growers, Inc. v. Paul, 
    373 U.S. 132
    , 142-43 (1963)). But conflict preemption is
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    broader than that; it also covers cases “where the challenged state law ‘stands as an
    obstacle to the accomplishment and execution of the full purposes and objectives
    of Congress.’” 
    Id.
     (quoting Hines v. Davidowitz, 
    312 U.S. 52
    , 67 (1941)). In this
    broader form, the lines between conflict preemption and field preemption are
    admittedly blurry, as the Supreme Court has recognized. See Crosby, 
    530 U.S. at
    372 n.6 (“[T]he categories of preemption are not rigidly distinct. Because a variety
    of state laws and regulations may conflict with a federal statute, whether because a
    private party cannot comply with both sets of provisions or because the objectives
    of the federal statute are frustrated, field pre-emption may be understood as a
    species of conflict pre-emption.” (citations and internal quotation marks omitted)).
    The essential question in this case is whether the Cuba Amendment stands as an
    obstacle to the carefully calibrated federal regime. “What is a sufficient obstacle is
    a matter of judgment, to be informed by examining the federal statute as a whole
    and identifying its purpose and intended effects.”       Crosby, 
    530 U.S. at 373
    .
    Because the conflict preemption analysis requires a searching inquiry into the
    provisions of both the federal and state laws at issue, we begin by examining, in
    some detail, the many federal statutes and regulations pertaining to Cuba.
    1.
    “Since the early 1960s, U.S. policy toward Cuba has consisted largely of
    isolating the island nation through comprehensive economic sanctions, including
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    an embargo on trade and financial transactions.” M.P. Sullivan, Cong. Research
    Serv. R41617, Cuba: Issues for the 112th Congress 30 (July 20, 2012) (“Cuba
    Issues”). The authority for, and contours of this federal policy come from a
    complex and interlocking network of statutes, regulations, and executive orders.
    Because our focus for present purposes is on the conflicts between the federal
    regime and the Cuba Amendment, which targets private companies, we highlight
    the provisions of the federal law that also affect private companies.
    The authority for the federal Cuba embargo dates back to 1917, when
    Congress empowered the President to regulate and embargo trade with foreign
    nations. See Trading with the Enemy Act, ch. 106, 
    40 Stat. 411
     (1917) (codified as
    amended at 50 U.S.C. app. §§ 1-6, 7-39, 41-44). The statute affords the President
    broad powers to regulate, license, and prohibit trade with foreign nations:
    [T]he President may, through any agency that he may designate, and
    under such rules and regulations as he may prescribe, by means of
    instructions, licenses, or otherwise --
    (A) investigate, regulate, or prohibit, any transactions in foreign
    exchange, transfers of credit or payments between, by, through, or to
    any banking institution, and the importing, exporting, hoarding,
    melting, or earmarking of gold or silver coin or bullion, currency or
    securities, and
    (B) investigate, regulate, direct and compel, nullify, void, prevent or
    prohibit, any acquisition holding, withholding, use, transfer,
    withdrawal, transportation, importation or exportation of, or dealing
    in, or exercising any right, power, or privilege with respect to, or
    transactions involving, any property in which any foreign country or a
    national thereof has any interest,
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    by any person, or with respect to any property, subject to the
    jurisdiction of the United States.
    50 U.S.C. app. § 5(b)(1).
    With respect to Cuba, the President has repeatedly exercised this power
    through the comprehensive Cuban Assets Control Regulations (“CACR”). The
    CACR were first promulgated by the Treasury Department in July 1963, almost
    fifty years ago. 1    The CACR are currently administered and enforced by the
    Treasury Department’s Office of Foreign Assets Control. See 31 C.F.R. pt. 515.
    The provisions of the CACR that most directly affect private companies
    relate to imports, exports, and other transactions involving Cuba or Cuban
    nationals.     Broadly speaking, the regulations prohibit, unless specifically
    authorized, any dealing in any property in which Cuba or a Cuban national has an
    1
    Since the enactment of the International Emergency Economic Powers Act of 1977, the
    President is only authorized to exercise the embargo powers conferred by Congress in that statute
    if the President first declares a national emergency, and may only exercise the powers conferred
    by the Trading with the Enemy Act during times of war. See 
    50 U.S.C. § 1701
    ; 
    id.
     app. § 5(b)(1)
    (empowering the President “[d]uring the time of war”). However, existing embargoes, such as
    the one against Cuba, were grandfathered in by Congress. As the Supreme Court has explained,
    “rather than requiring the President to declare a new national emergency in order to continue
    existing economic embargoes, such as that against Cuba, Congress decided to grandfather
    existing exercises of the President’s ‘national emergency’ authorities.” Regan v. Wald, 
    468 U.S. 222
    , 228 (1984). “This grandfather provision also provided that ‘[t]he President may extend the
    exercise of such authorities for one-year periods upon a determination for each such extension
    that the exercise of such authorities with respect to such country for another year is in the
    national interest of the United States.’” 
    Id. at 229
     (quoting 50 U.S.C. app. § 5 note). The CACR
    promulgated in the 1960’s are still valid by virtue of these extensions as well as by Congress’
    subsequent codification in 1996 of the economic embargo against Cuba, see 
    22 U.S.C. § 6032
    (h), though the regulations have been “alternately loosened and tightened in response to
    specific circumstances,” Wald, 
    468 U.S. at 243
    .
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    interest of any nature. See 
    31 C.F.R. § 515.201
    (a), (b). “Property” is expansively
    defined to include not only tangible property, but also contracts, securities, and
    services as well. 
    31 C.F.R. § 515.311
    (a). These provisions also apply to exports to
    Cuba, whether from the U.S. or even through offshore dealing by a person or entity
    subject to the CACR, because by definition a product exported to Cuba is one in
    which Cuba or a Cuban national has an interest. In keeping with the regulations’
    expansive definition of property, the ban on exports covers not only tangible
    goods, but also “the exportation of securities, currency, checks, drafts and
    promissory notes.” 
    31 C.F.R. § 515.405
    .
    The CACR also specifically prohibit importation or other dealings in
    merchandise that is of Cuban origin or is made from products of Cuban origin or
    has been located in or transported from or through Cuba. 
    31 C.F.R. §§ 515.204
    ,
    515.410; see also 
    22 U.S.C. § 6040
    (a) (“The Congress notes that section 515.204
    of title 31, Code of Federal Regulations, prohibits the entry of, and dealings
    outside the United States in, merchandise that . . . is of Cuban origin; . . . is or has
    been located in or transported from or through Cuba; or . . . is made or derived in
    whole or in part of any article which is the growth, produce, or manufacture of
    Cuba.”). Related to the ban on imports are restrictions placed on vessels that have
    engaged in trade with Cuba. Subject to waiver for certain vessels engaging in
    licensed or exempt trade, “[n]o vessel carrying goods or passengers to or from
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    Cuba or carrying goods in which Cuba or a Cuban national has an interest may
    enter a U.S. port with such goods or passengers on board.”                 
    31 C.F.R. § 515.207
    (b). Moreover, no vessel that enters Cuba for trade may enter a U.S. port
    for a period of 180 days from the date the vessel departed from Cuba. 
    31 C.F.R. § 515.207
    (a).
    Notably, the CACR only place restrictions on any “[p]erson . . . subject to
    the jurisdiction of the United States,” 50 U.S.C. app. § 5(b)(1), which is defined by
    regulation to include U.S. corporations, their domestic and foreign subsidiaries,
    and any foreign company owned or controlled by a U.S. citizen. 
    31 C.F.R. § 515.329
    . There is nothing in this record to suggest that Odebrecht has run afoul of
    the CACR, because neither it nor any of its subsidiaries does any business with
    Cuba. Significantly, the CACR do not sanction a U.S. company like Odebrecht for
    the business activities of its foreign parent company or of a distant foreign affiliate
    that shares a common parent company.
    Congress has remained active in legislating with respect to Cuba, and the
    current CACR reflect the additional sanctions and exceptions Congress has crafted
    over many years. Thus, the Cuban Democracy Act of 1992, codified at 
    22 U.S.C. §§ 6001-6010
    , ramped up economic sanctions against the Cuban government while
    simultaneously permitting humanitarian relief to the Cuban people. See generally
    
    22 U.S.C. §§ 6001-6002
     (congressional findings and statements of policy).
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    Additional comprehensive legislation came four years later, when Cuban MiG’s
    shot down two U.S. civilian private planes in February 1996. See 
    22 U.S.C. § 6046
     (Congressional findings condemning attack). Shortly thereafter, Congress
    enacted the Cuban Liberty and Democratic Solidarity Act of 1996 (“Libertad Act”
    or “Helms-Burton Act”), 
    22 U.S.C. §§ 6021-6091
    . One of the provisions of the
    Act codifies the regulatory sanctions that were in place on March 1, 1996. See 
    22 U.S.C. § 6032
    (h) (“The economic embargo of Cuba, as in effect on March 1, 1996,
    including all restrictions under part 515 of title 31, Code of Federal Regulations,
    shall be in effect on March 12, 1996, and shall remain in effect, subject to section
    6064 of this title.”). As a panel of this Court has previously explained, this
    provision of the Helms-Burton Act “continues the embargo indefinitely and
    effectively suspends the . . . requirement that the President revisit the embargo
    each year.” See United States v. Plummer, 
    221 F.3d 1298
    , 1308 n.6 (11th Cir.
    2000). Congress subsequently relaxed some of the Helms-Burton Act’s sanctions
    in the Trade Sanctions Reform and Export Enhancement Act of 2000, codified at
    
    22 U.S.C. §§ 7201-7209
    , which loosened the restrictions on exporting agricultural
    and medical products to Cuba.
    In short, the economic embargo against Cuba is pervasive. But the federal
    regime also contains numerous exceptions, permitting certain kinds of transactions
    with Cuba through licensing as well as through complete exemptions. One of the
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    major exemptions is for published and informational materials, whether
    commercial or otherwise, 
    31 C.F.R. § 515.206
    (a), which includes “[p]ublications,
    films, posters, phonograph records, photographs, microfilms, microfiche, tapes,
    compact disks, CD ROMs, artworks, news wire feeds, and other information and
    informational articles,” 
    31 C.F.R. § 515.332
    . In addition, the Helms-Burton Act
    authorizes the President to establish and implement an exchange of news bureaus
    between the U.S. and Cuba if certain conditions are met. 
    22 U.S.C. § 6044
    .
    Another substantial category of exceptions is for agricultural and medical
    products. The Cuban Democracy Act provides that “[e]xports of medicines or
    medical supplies, instruments, or equipment to Cuba shall not be restricted” except
    under certain circumstances, such as where there is a reasonable probability that
    the product will be used in human rights abuses, will be reexported, or could be
    used in the production “of any biotechnological product.” 
    22 U.S.C. § 6004
    (c). In
    addition, the Trade Sanctions Reform and Export Enhancement Act of 2000
    prevents the President from imposing any unilateral agricultural sanction or
    medical sanction against a foreign country or foreign entity unless Congress
    approves it, again subject to certain exceptions. 
    22 U.S.C. §§ 7202
    , 7203. The
    statute also terminated any existing unilateral agricultural or medical sanction in
    effect as of October 28, 2000. 
    Id.
     The statute does provide, however, that any
    export of agricultural commodities, medicine or medical devices to Cuba must be
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    done pursuant to 1-year licenses issued by the United States Government. 
    Id.
     §
    7205(a). Moreover, the exemption applies only to exports to Cuba, and does not
    affect the ban on importation of goods from Cuba. Id. § 7208. The statute also
    directs the Secretary of the Treasury to promulgate regulations providing for
    general licenses to travel to, from, or within Cuba for the marketing and sale of
    agricultural and medical goods. Id. § 7209(a); accord 
    31 C.F.R. §§ 515.533
    (e),
    515.560 (provisions of CACR authorizing travel and travel-related transactions
    incident to sales of agricultural commodities, medicine, or medical devices).
    A final and important exception from the Cuba sanctions is for
    telecommunications     services.      The     Cuban     Democracy    Act    permits
    telecommunications services between the United States and Cuba, and authorizes
    telecommunications facilities as may be necessary “to provide efficient and
    adequate telecommunications services between the United States and Cuba.” 
    22 U.S.C. § 6004
    (e)(1), (2). It does not authorize, however, any investment by a
    United States person in a domestic telecommunications network within Cuba. 
    Id.
    § 6004(e)(5). The CACR further authorize U.S. telecommunications providers to
    engage in all transactions incident to the provision of telecommunications services
    or satellite radio or television services between the United States and Cuba. 
    31 C.F.R. § 515.542
    .    The regulations also authorize persons or entities covered by
    the regulations to enter into and pay for contracts with non-Cuban
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    telecommunications providers to provide telecommunications services to
    individuals within Cuba, so long as the Cuban individuals receiving the services
    are not members of the Cuban government. 
    31 C.F.R. § 515.542
    (c). As with the
    agricultural and medical exceptions, the CACR also authorize travel and travel-
    related expenses in connection with the marketing, sale, and provision of
    telecommunications services. 
    31 C.F.R. § 515.533
    (f).
    We do not labor on these points to comment on the wisdom or efficacy of
    the federal Cuban sanctions regime or its exceptions, but rather simply to show that
    the executive branch has considerable authority and discretion in the field of
    Cuban sanctions, and has actively exercised that authority, just as Congress has
    actively legislated. Federal policy towards Cuba is long-standing, it is nuanced, it
    is highly calibrated, and it is constantly being fine-tuned. It is designed to sanction
    strongly the Castro regime while simultaneously permitting humanitarian relief and
    economic transactions that will benefit the Cuban people. When the State of
    Florida promulgated the Cuba Amendment, it plainly was not operating in an area
    where the federal government has been asleep at the switch.
    2.
    It is against this substantial backdrop of federal law that Governor Rick
    Scott, on May 1, 2012, signed into law the Committee Substitute for Committee
    Substitute for House Bill 959, which is codified at Chapter 2012-196, § 2, Laws of
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    Florida. More commonly known as the “Cuba Amendment,” this law provides in
    relevant part that a company “engaged in business operations in Cuba or Syria, is
    ineligible for, and may not bid on, submit a proposal for, or enter into or renew a
    contract with an agency or local governmental entity for goods or services of $1
    million or more.” 
    Fla. Stat. § 287.135
    (2). 2 In other words, the law cuts off access
    to Florida’s substantial public contracting market, which is worth some $8 billion a
    year at the state level alone, not including local government contracts. The Cuba
    Amendment’s effective date was July 1, 2012, although the district court’s
    preliminary injunction was entered before that date and has prevented the law from
    being enforced.
    Each crucial term in the state statute is defined broadly.               “Business
    operations” means “engaging in commerce in any form in Cuba . . ., including, but
    not limited to, acquiring, developing, maintaining, owning, selling, possessing,
    leasing, or operating equipment, facilities, personnel, products, services, personal
    property, real property, military equipment, or any other apparatus of business or
    commerce.”      
    Id.
     § 287.135(1)(b).        And most notably for our purposes, a
    “company” is defined as any “entity or business association, including all wholly
    owned subsidiaries, majority-owned subsidiaries, parent companies, or affiliates of
    such entities or business associations, that exists for the purpose of making profit.”
    2
    The Cuba Amendment’s application to companies doing business in Syria has not been
    challenged in this case, and is not before us on appeal.
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    Fla. Stat. § 215.473
    (c) (emphases added). In other words, as the district court aptly
    summarized, “the Cuba Amendment effectively encompasses domestic companies
    with no connection to Cuba other than by proxy.” Although neither Odebrecht nor
    any subsidiary of Odebrecht does business in Cuba, the Cuba Amendment applies
    to Odebrecht, because Odebrecht has distant foreign affiliates -- COI Overseas Ltd.
    and Companhia de Obras e Infra-Estrutura -- that share a common parent company
    with Odebrecht and that are involved in a project to expand the Port of Mariel in
    Cuba.
    The broad reach of the Cuba Amendment and its applicability to Odebrecht
    are not in dispute. The Florida State Board of Administration’s own preliminary
    list estimates that the Cuba Amendment applies to 238 companies that the State
    invests in, including “major airlines, banks, pharmaceuticals and oil companies.”
    Nor is it seriously in dispute that the purpose of the Cuba Amendment is to
    use the lever of access to Florida’s $8 billion-a-year public contracting market to
    exert additional economic pressure on the Cuban government and to influence
    American foreign policy. Governor Scott acknowledged as much when he signed
    the Cuba Amendment into law, stating in a letter to Florida Secretary of State Ken
    Detzner that the Cuba Amendment “demonstrates Florida’s commitment to
    spreading political and economic freedom in Cuba” and that “[i]t is imperative that
    18
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    Florida and the United States continue to place economic pressure” on the Cuban
    government.
    The Cuba Amendment is enforced through the public bidding process. “At
    the time a company submits a bid or proposal for a contract or before the company
    enters into or renews a contract with an agency or governmental entity for goods or
    services of $1 million or more, the company must certify . . . that it does not have
    business operations in Cuba . . . .” 
    Fla. Stat. § 287.135
    (5). If a company files a
    false certification, it is subject to a “civil penalty equal to the greater of $2 million
    or twice the amount of the contract” and it becomes “ineligible to bid on any
    contract with an agency or local governmental entity for 3 years.”                 
    Id.
     §
    287.135(5)(a)(1)-(2).    The civil penalty is enforced by the agency or local
    governmental entity that is a party to the contract; there is no private right of
    enforcement by unsuccessful bidders or by “any other person other than the agency
    or local governmental entity.” Id. § 287.135(6).
    Finally, we note that foreign governments have complained to the United
    States about the Cuba Amendment, both prior to and following its enactment.
    Most notably, Canada and Brazil, Florida’s two largest foreign trading partners,
    both have protested the Cuba Amendment. For instance, the office of the Canadian
    ambassador to the United States placed a phone call to the Florida Chamber of
    Commerce, expressing concern that the law would affect a slew of Canadian
    19
    Case: 12-13958     Date Filed: 05/06/2013    Page: 20 of 44
    companies that work in both Florida and Cuba.            The Brazilian Minister of
    Development, Industry, and Trade lodged a similar note with the United States
    Commerce Secretary, John Bryson, conveying Brazil’s “deep concern” with the
    adverse effects of the Cuba Amendment, in particular its effects on the “growing
    bilateral trade” between the United States and Brazil.
    Several parties to the World Trade Organization (“WTO”), including the
    European Union, Canada, Norway, Switzerland, and Singapore, also expressed
    concern that the Cuba Amendment conflicts with the United States’ commitments
    under the Agreement on Government Procurement.                WTO, Committee on
    Government Procurement, Minutes of the Formal Meeting of 18 July 2012 ¶¶ 25-
    37. The WTO Meeting took place after the district court entered its preliminary
    injunction, but the EU “sought general information from the United States on the
    Florida law, including relevant references and information on the on-going court
    proceedings regarding the validity of the law, in particular in regard to the potential
    expiry of the injunction” and reiterated that it “wished to be informed and updated
    about any changes regarding the situation, on a regular basis.” Id. ¶¶ 27, 34. Other
    parties expressed similar sentiments. E.g. id. ¶¶ 29-30 (statements of Canada and
    Norway).
    B.
    20
    Case: 12-13958       Date Filed: 05/06/2013      Page: 21 of 44
    The briefest summary of both the federal and state laws now before us
    reveals the obvious, direct and apparent conflict between them. Our analysis is
    guided in no small measure by the unanimous judgment of the Supreme Court in
    Crosby v. National Foreign Trade Council, 
    530 U.S. 363
     (2000). At issue in
    Crosby was the constitutionality of a Massachusetts law that, like the State of
    Florida, prohibited state agencies from purchasing goods or services from any
    person or entity doing business with Burma, with a few exceptions for companies
    that are in Burma solely to report the news or to provide international
    telecommunications goods or services or medical supplies. 
    530 U.S. at 367
    .3
    Three months after the Massachusetts law was passed, Congress passed a statute
    imposing a set of mandatory and conditional sanctions on Burma. 
    Id. at 368
    . The
    federal statute banned “all aid to the Burmese Government except for humanitarian
    assistance, counternarcotics efforts, and promotion of human rights and
    democracy.” 
    Id.
     It also required U.S. representatives to international financial
    institutions to vote against loans or other assistance to or for Burma, and it cut off
    entry visas to Burmese government officials unless required by treaty or to staff the
    Burmese mission to the United Nations. 
    Id.
     The statute delegated to the President
    3
    The Cuba Amendment does not contain these limited exceptions. Indeed, the United States
    Telecom Association has filed an amicus brief in support of Odebrecht, which points out that the
    federal sanctions regimes for state sponsors of terrorism -- Iran, Syria, Sudan, and Cuba -- all
    include exemptions for the provision of international telecommunications services and that the
    Cuba Amendment therefore punishes what the federal law expressly permits. See Br. for United
    States Telecom Association as Amicus Curiae at 18-25.
    21
    Case: 12-13958       Date Filed: 05/06/2013      Page: 22 of 44
    the authority to end the sanctions once he “determines and certifies to Congress
    that Burma has made measurable and substantial progress in improving human
    rights practices and implementing democratic government.” 
    Id.
     The statute also
    empowered the President to impose further sanctions under certain conditions and
    directed the President to develop a comprehensive, multilateral strategy to bring
    democracy to, and improve quality of life and human rights practices in Burma.
    
    Id. at 369
    . President Clinton exercised the authority granted him by the statute and
    issued an executive order imposing further sanctions on Burma, prohibiting “new
    investment” in Burma by U.S. persons or entities and “generally incorporat[ing]
    the exceptions and exemptions addressed in the statute.” 
    Id. at 370
    .
    It was against this federal backdrop that the Supreme Court scrutinized the
    Massachusetts law. Justice Souter’s opinion for seven of the justices 4 concluded
    that “[b]ecause the state Act’s provisions conflict with Congress’s specific
    delegation to the President of flexible discretion, with limitation of sanctions to a
    limited scope of actions and actors, and with direction to develop a comprehensive,
    multilateral strategy under the federal Act, it is preempted, and its application is
    unconstitutional, under the Supremacy Clause.” 
    Id. at 388
    . The Court found that
    the state law undermined the purpose and natural effect of at least three provisions
    of the federal law: “its delegation of effective discretion to the President to control
    4
    Justice Scalia, joined by Justice Thomas, concurred in the judgment only. See 
    530 U.S. at
    388-
    391 (Scalia, J., concurring).
    22
    Case: 12-13958    Date Filed: 05/06/2013   Page: 23 of 44
    economic sanctions against Burma, its limitation of sanctions solely to United
    States persons and new investment, and its directive to the President to proceed
    diplomatically in developing a comprehensive, multilateral strategy toward
    Burma.” 
    Id. at 373-74
    . In other words, the state law weakened the President’s
    discretion to calibrate economic sanctions against Burma using the authority
    conferred by Congress, and also displaced the President’s exercise of that
    discretion by punishing conduct that the federal law permits and exceeding the
    “specific range” of pressure Congress intended to impose against the Burmese
    Government. 
    Id. at 377
    .
    All of the concerns animating the Supreme Court’s decision in Crosby are
    present here -- and to a far greater degree. Undeniably, the Cuba Amendment
    conflicts with federal law in (at least) three ways: (1) the Cuba Amendment sweeps
    more broadly than the federal regime does, punishing companies like Odebrecht
    that do not run afoul of the federal Cuban sanctions and penalizing economic
    conduct that the federal law expressly permits; (2) the Cuba Amendment has its
    own substantial penalties that go beyond the federal sanctions; and (3) the Cuba
    Amendment undermines the substantial discretion Congress has afforded the
    President both to fine-tune economic sanctions and to pursue multilateral strategies
    with Cuba. We discuss each in turn.
    1.
    23
    Case: 12-13958        Date Filed: 05/06/2013        Page: 24 of 44
    The Trading with the Enemy Act, which provides the statutory basis for the
    Cuban Assets Control Regulations, only applies to a “[p]erson . . . subject to the
    jurisdiction of the United States,” 50 U.S.C. app. § 5(b)(1). The CACR further
    define that term as follows:
    The term “person subject to the jurisdiction of the United States”
    includes:
    (a) Any individual, wherever located, who is a citizen or resident of
    the United States;
    (b) Any person within the United States as defined in § 515.330
    [which, in relevant part, means a “person actually within the United
    States,” 
    31 C.F.R. § 515.330
    (b)];
    (c) Any corporation, partnership, association, or other organization
    organized under the laws of the United States or of any State,
    territory, possession, or district of the United States; and
    (d) Any corporation, partnership, association, or other organization,
    wherever organized or doing business, that is owned or controlled by
    persons specified in paragraphs (a) or (c) of this section.
    
    31 C.F.R. § 515.329
    . The CACR thus apply to the following groups: U.S. citizens
    or residents, wherever located; any person located in the United States; any U.S.
    corporation; any corporation, wherever located, that is owned or controlled by a
    U.S. citizen or resident; and any corporation, wherever located, owned or
    controlled by a U.S. corporation (i.e. a foreign subsidiary of a U.S. corporation).5
    5
    The statutes relating to Cuba do not have a materially different scope in terms of the entities
    covered. The Cuban Democracy Act’s prohibition on licensing import or export transactions
    between U.S.-owned or controlled foreign firms and Cuba, 
    22 U.S.C. § 6005
    (a)(1), explicitly
    24
    Case: 12-13958        Date Filed: 05/06/2013       Page: 25 of 44
    None of the federal sanctions reach as far as the Cuba Amendment. The
    Amendment applies to any “company” that is “engaged in business operations in
    Cuba.” 
    Fla. Stat. § 287.135
    (2). Critically, a “company” for purposes of the Cuba
    Amendment is actually an entire corporate network, because it covers any “entity
    or business association, including all wholly owned subsidiaries, majority-owned
    subsidiaries, parent companies, or affiliates of such entities or business
    associations, that exists for the purpose of making profit.” 
    Fla. Stat. § 215.473
    (c)
    (emphases added).
    The Cuba Amendment plainly sweeps further than the federal regime
    because it imposes a penalty on a U.S. corporation like Odebrecht that does not
    itself do business with Cuba, but has a foreign parent company that does business
    with Cuba through an unrelated foreign subsidiary. Or, in simpler terms, the Cuba
    Amendment penalizes U.S. companies for the business activities of their foreign
    parents or their foreign affiliates, no matter how remote the connection. This
    squarely conflicts with the federal regime, which only sanctions U.S. companies
    for their own actions or the actions of their own subsidiaries.
    cross-references the CACR provision on the subject, which applies to “U.S.-owned or controlled
    firms in third countries,” 
    31 C.F.R. § 515.559
    . Similarly, in the Libertad Act there are various
    provisions that apply to a “United States national,” which is defined by the statute as “any United
    States citizen” or “any other legal entity which is organized under the laws of the United States,
    or of any State, the District of Columbia, or any commonwealth, territory, or possession of the
    United States, and which has its principal place of business in the United States.” 
    22 U.S.C. § 6023
    (15). In other words, U.S. citizens and U.S. corporations.
    25
    Case: 12-13958    Date Filed: 05/06/2013   Page: 26 of 44
    The Cuba Amendment sweeps more broadly than the federal regime not
    only in the entities covered, but also in the conduct penalized. As we’ve noted, the
    federal regime, through licenses and exemptions, carves out from the Cuban
    sanctions certain categories of transactions with Cuba that are designed to support
    the Cuban people. These exceptions include the export to Cuba of published and
    informational material, agricultural commodities, drugs and medical devices, and
    telecommunications services. The Cuba Amendment plainly conflicts with federal
    law because it does not countenance any of the federal regime’s exceptions. Any
    private company that engages in “business operations” in Cuba, or has a foreign
    parent company or affiliate that does so, is subject to the Cuba Amendment’s
    restrictions. And “business operations,” as defined in the Florida statute, means
    “engaging in commerce in any form in Cuba.”             
    Fla. Stat. § 287.135
    (1)(b)
    (emphasis added). No exceptions, no carve-outs for certain goods, services or
    transactions, no calibrated licensing system.    The Cuba Amendment, in stark
    contrast to the federal regime, penalizes any commerce with Cuba -- no ifs, ands,
    or buts. Indeed, counsel for FDOT conceded in the district court that the Cuba
    Amendment has “no such exceptions where we say that certain types of contractual
    arrangements with Cuba would be accepted.”
    Thus the Cuba Amendment again squarely conflicts with the more nuanced
    federal regime. “Sanctions are drawn not only to bar what they prohibit but to
    26
    Case: 12-13958     Date Filed: 05/06/2013   Page: 27 of 44
    allow what they permit, and the inconsistency of sanctions here undermines the
    congressional calibration of force.” Crosby, 
    530 U.S. at 380
    . Simply put, the
    Cuba Amendment conflicts with federal law “by penalizing individuals and
    conduct that Congress has explicitly exempted or excluded from sanctions.” 
    Id. at 378
    . This it may not do.
    2.
    The Cuba Amendment also conflicts with federal law because it imposes
    additional penalties on those companies that are subject to the federal sanctions.
    “Conflict is imminent when two separate remedies are brought to bear on the same
    activity.”   Crosby, 
    530 U.S. at 376
     (internal quotation marks and alteration
    omitted). The Trading with the Enemy Act establishes the penalties for violating
    any of the federal Cuban sanctions. The statute provides for criminal penalties of
    up to 20 years’ imprisonment and a $1,000,000 fine for a willful violation, and a
    civil penalty of up to $50,000 for a violation. 50 U.S.C. app. § 16(a), (b)(1). Any
    property that is the subject of a violation is subject to forfeiture in both the civil
    and criminal contexts. Id. app. § 16(b)(2), (c). In addition, any transfer of property
    in violation of the CACR is deemed null and void and cannot form the basis of an
    interest in the subject property. 
    31 C.F.R. § 515.203
    .
    The administrative enforcement process is detailed more fully in the CACR.
    See 
    31 C.F.R. §§ 501.703
     - 501.747. In addition, Appendix A to the CACR,
    27
    Case: 12-13958       Date Filed: 05/06/2013      Page: 28 of 44
    entitled “Economic Sanctions Enforcement Guidelines,” “provides a general
    framework for the enforcement of all economic sanctions programs administered
    by the Office of Foreign Assets Control.” The guidelines detail a number of
    possible administrative responses to an apparent violation, ranging from No Action
    to Criminal Referral. 31 C.F.R. pt. 501 app. A, Part II (A)-(G). 6 Part III of the
    guidelines sets forth general factors affecting the choice of which administrative
    action to pursue, including willfulness, concealment, pattern of conduct, prior
    notice, involvement of management, awareness of the violation, harm to the
    sanctions program’s objectives, size of economic or other benefit conferred on the
    violator, commercial sophistication of the violator, and so on. 
    Id.
     app. A, Part III.
    The Cuba Amendment plainly imposes additional penalties above and
    beyond the federal regime. Prohibiting a company from bidding on state or local
    contracts in Florida is a substantial punishment, especially when applied to
    companies that may not even be in violation of the federal regime. And the
    enforcement mechanism for this prohibition -- a “civil penalty equal to the greater
    of $2 million or twice the amount of the contract” and a three year ban on public
    contracting if a company files a false certification about its business relations with
    Cuba, 
    Fla. Stat. § 287.135
    (5)(a) -- is considerably greater than the federal regime’s
    6
    The possible actions listed in the guidelines are No Action, Request Additional Information,
    Cautionary Letter, Finding of Violation, Civil Monetary Penalty, Criminal Referral, and Other
    Administrative Actions (which include License Denial, Suspension, Modification, or
    Revocation, or a Cease and Desist Order).
    28
    Case: 12-13958      Date Filed: 05/06/2013    Page: 29 of 44
    civil penalty of up to $50,000. Indeed, the penalty is, at a minimum, twice as large
    as the criminal fine for willful violations of the federal sanctions. The Cuba
    Amendment thus stands in sharp contrast to the federal calibration of appropriate
    penalties as well.
    The Florida Department of Transportation concedes that the penalties
    imposed by the Cuba Amendment are different, but claims they penalize different
    conduct. FDOT argues that companies are not being punished for doing business
    in Cuba, but rather for lying about it when they submit a false certification. This
    purported distinction -- punishing the lie, not the trade conduct itself -- is
    unpersuasive. It also fails to take into account that prohibiting companies like
    Odebrecht from bidding on Florida public contracts in the first place is itself a
    substantial punishment that exceeds the federal sanctions regime in both penalty
    and reach. That punishment does not depend on any false certifications, only on
    business relations with Cuba by a company or by its foreign parent or affiliate.
    FDOT’s observation that the federal government also denounces the Castro regime
    and designates Cuba as a state sponsor of terrorism, while undeniably true, is of
    little help to the agency, because “[t]he fact of a common end hardly neutralizes
    conflicting means.” Crosby, 
    530 U.S. at
    379-80 (citing Gade, 
    505 U.S. at 103
    ).
    Choosing “the right degree of pressure to employ” against the Castro regime is a
    “federal decision,” id. at 380, not a decision for the State of Florida.
    29
    Case: 12-13958     Date Filed: 05/06/2013    Page: 30 of 44
    3.
    The federal government has employed an extensive array of economic
    sanctions against Cuba for almost 50 years. By any measure, the Cuban sanctions
    embodied in federal law are far more extensive than the federal sanctions leveled
    against Burma, which did not even exist at the time Massachusetts passed the
    selective procurement law before the Supreme Court in Crosby. As we’ve noted,
    Congress has passed numerous statutes, the executive branch has promulgated the
    Cuban Assets Control Regulations, which are enforced by the Department of the
    Treasury, and the President has enormous discretion to calibrate the sanctions
    therein. Significantly, the federal statutes also afford the President, in consultation
    with Congress, the discretion to waive sanctions and even terminate the embargo
    as Cuba transitions to a democratic government. See 
    22 U.S.C. §§ 6007
    , 6064.
    The considerable discretion afforded the President has been amply
    evidenced by the periodic tightening and loosening of sanctions related to travel,
    enforcement levels, agricultural and medical supplies, remittances, and
    humanitarian aid. In January 1999, President Clinton loosened some sanctions,
    announcing measures to support the Cuban people such as broadening cash
    remittances to Cuba to all U.S. residents, not just those with close relatives in
    Cuba; expanding direct flights to Cuba beyond just Miami; and loosening
    restrictions on travel to Cuba for certain travelers, such as professional researchers
    30
    Case: 12-13958    Date Filed: 05/06/2013   Page: 31 of 44
    and those involved in certain educational, religious, and sports activities. See Cuba
    Issues at 31. President Bush, on the other hand, emphasized stronger enforcement
    of economic sanctions and tightened the restrictions on travel, remittances, and
    humanitarian gift parcels to Cuba. See id. at 31-32. President Obama has, in turn,
    relaxed the restrictions on travel and remittances, allowing, for example, religious
    organizations to sponsor religious travel to Cuba and accredited institutions of
    higher education to sponsor travel to Cuba as well. President Obama has also
    allowed any U.S. person to send remittances to non-family members in Cuba to
    support private economic activity. See id. at 33-36. In other words, President
    Obama has largely restored President Clinton’s policies, which had been tightened
    in the interim by President Bush. See id. at 36 (“In most respects, [President
    Obama’s] new measures appear to be similar to policies that were undertaken by
    the Clinton Administration in 1999, but were subsequently curtailed by the Bush
    Administration in 2003 and 2004.”). Plainly, Congress has reposed considerable
    power in the President to adjust our Nation’s sanctions against the Cuban
    Government.
    It is hard to dispute that the Cuba Amendment undermines the President’s
    capacity to fine-tune these sanctions and to direct diplomatic relations with Cuba.
    “It is not merely that the differences between the state and federal Acts in scope
    and type of sanctions threaten to complicate discussions; they compromise the very
    31
    Case: 12-13958        Date Filed: 05/06/2013   Page: 32 of 44
    capacity of the President to speak for the Nation with one voice in dealing with
    other governments.” Crosby, 
    530 U.S. at 381
    . The President’s “maximum power
    to persuade rests on his capacity to bargain for the benefits of access to the entire
    national economy without exception for enclaves fenced off willy-nilly by
    inconsistent political tactics.”     
    Id.
     (emphasis added).     The Cuba Amendment
    creates a large “enclave[]” that the President can no longer offer in bargaining with
    Cuba: access to Florida’s public contracting market, worth $8 billion a year at the
    state level alone, not counting local government contracts. Moreover, just like in
    Crosby, “the record is replete with evidence to answer any skeptics” about the
    undermining of national policy. 
    Id. at 382
    . The negative foreign response to the
    Cuba Amendment has been similar to the negative foreign response to
    Massachusetts’s Burma law. In Crosby, the Supreme Court noted that the EU and
    Japan diplomatically protested the Massachusetts law and lodged formal
    complaints in the WTO. 
    Id. at 382-83
    . Here, as we’ve noted, numerous foreign
    powers, including Canada, Brazil, the European Union, and Norway have all
    lodged protests against the Cuba Amendment through various diplomatic channels
    and through the WTO.
    The conflict between state and federal law is all the more apparent because
    the President is acting at the zenith of his power when he exercises the discretion
    afforded him by Congress to direct our Nation’s economic policy towards Cuba.
    32
    Case: 12-13958     Date Filed: 05/06/2013   Page: 33 of 44
    As Justice Jackson observed over sixty years ago, “[w]hen the President acts
    pursuant to an express or implied authorization of Congress, his authority is at its
    maximum, for it includes all that he possesses in his own right plus all that
    Congress can delegate.” Youngstown Sheet & Tube Co. v. Sawyer, 
    343 U.S. 579
    ,
    635 (1952) (Jackson, J., concurring). Moreover, the President’s power in the area
    of foreign relations is already among his most substantial, because in the “vast
    external realm” of foreign affairs, “with its important, complicated, delicate and
    manifold problems, the President alone has the power to speak or listen as a
    representative of the nation.” United States v. Curtiss-Wright Exp. Corp., 
    299 U.S. 304
    , 319 (1936).     Thus, we are especially mindful of state laws that might
    undermine the exercise of the President’s large discretion in this area.
    Plainly, the Cuba Amendment is such a law. It exceeds the scope of the
    federal Cuban sanctions in numerous ways, as we have explained. Moreover, the
    federal laws related to Cuba demonstrate a “plentitude of Executive authority” to
    “exercise economic leverage” against the Castro regime. Crosby, 
    530 U.S. at
    375-
    76. It was precisely this “plentitude of Executive authority” that the Supreme
    Court found “controls the issue of preemption,” because “[t]he President has been
    given this authority not merely to make a political statement but to achieve a
    political result, and the fullness of his authority shows the importance of the
    congressional mind of reaching that result.” 
    Id. at 376
    . The federal laws empower
    33
    Case: 12-13958     Date Filed: 05/06/2013    Page: 34 of 44
    the President to engage in a multilateral approach to Cuba, with economic
    sanctions designed to weaken the Castro regime but with notable exceptions to
    support the Cuban people. The enforcement of the Cuba Amendment overrides the
    nuanced federal policy and creates a large enclave that the President can no longer
    access. As the Supreme Court explained, “[i]t is simply implausible that Congress
    would have gone to such lengths to empower the President if it had been willing to
    compromise his effectiveness by deference to every provision of state statute or
    local ordinance that might, if enforced, blunt the consequences of discretionary
    Presidential action.” 
    Id.
     As we see it, the Cuba Amendment “stands as an obstacle
    to the accomplishment and execution of the full purposes and objectives of
    Congress” in its delegation of discretionary authority to the President, as well as its
    own legislation on Cuban sanctions, including the Cuban Democracy Act and the
    Helms-Burton Act. 
    Id. at 373
     (quoting Hines, 
    312 U.S. at 67
    ).
    C.
    The State tries to get around the Supreme Court’s controlling precedent and
    the clear conflict between state and federal law in a few ways.             First, the
    Department argues that the State’s choice of how to allocate and spend public
    funds is a basic aspect of its sovereignty that should be immune or nearly immune
    from judicial review and not amenable to preemption analysis. But the preempted
    state law before the Supreme Court in Crosby was also a spending law involving
    34
    Case: 12-13958      Date Filed: 05/06/2013   Page: 35 of 44
    the use of state funds in public contracting. Indeed, this exact argument was
    briskly rejected by the Court:
    We add that we have already rejected the argument that a State’s
    “statutory scheme . . . escapes pre-emption because it is an exercise of
    the State’s spending power rather than its regulatory power.”
    Wisconsin Dept. of Industry v. Gould, Inc., 
    475 U.S. 282
    , 287, 
    106 S.Ct. 1057
    , 
    89 L.Ed.2d 223
     (1986). In Gould, we found that a
    Wisconsin statute debarring repeat violators of the National Labor
    Relations Act, 
    29 U.S.C. § 151
     et seq., from contracting with the State
    was preempted because the state statute’s additional enforcement
    mechanism conflicted with the federal Act. 
    475 U.S., at
    288–289, 
    106 S.Ct. 1057
    . The fact that the State “ha[d] chosen to use its spending
    power rather than its police power” did not reduce the potential for
    conflict with the federal statute. 
    Ibid.
    530 U.S. at 
    373 n.7 (alterations in original).
    The Department also says that our own post-Crosby decision in Faculty
    Senate of Florida International University v. Winn, 
    616 F.3d 1206
     (11th Cir.
    2010), is controlling. In Faculty Senate, a panel of this Court upheld portions of
    Florida’s Travel Act, 
    Fla. Stat. §§ 112.061
    (3)(e), 1011.90(6), which restricted state
    universities from spending funds given to them by the State on travel to a country
    designated by the United States Department of State as a state sponsor of terrorism,
    which includes Cuba. The panel “presume[d] that the State can validly legislate on
    spending and on education matters,” but recognized that “these traditional state
    concerns could be overridden” in the event of a clear conflict with federal law or
    policy. 
    616 F.3d at 1208
    . However, the Florida statute’s “brush with federal law
    and the foreign affairs of the United States [was] too indirect, minor, incidental,
    35
    Case: 12-13958    Date Filed: 05/06/2013   Page: 36 of 44
    and peripheral to trigger the Supremacy Clause’s-undoubted-overriding power.”
    
    Id.
     Given “the lack of the conflict’s clarity and severity,” the strength of Florida’s
    interest in managing its own education spending and funding of its employees’
    travel was sufficient to overcome any nebulous conflict with federal policy. 
    Id. at 1211
    .
    We distinguished Crosby because Florida, in passing its Travel Act, did not
    “unilaterally select[] by name a foreign country on which it ha[d] declared, in
    effect, some kind of economic war.” 
    Id. at 1210
    . In addition, Florida’s law neither
    prohibited nor penalized anyone for traveling anywhere. See 
    id.
     Importantly,
    Florida’s law also did “not attempt to prohibit, or even to obstruct, trading broadly
    by anyone with anyone.” 
    Id.
     Although not willing to hold it relevant, the panel
    also noted that the economic impact was likely minimal. See id. & n.10 (observing
    that, from 2001-2006, the Cuban Research Institute at Florida International
    University spent $125,511 on direct travel expensed to and from Cuba, and
    remarking that such sums likely “are not big enough to be of serious concern on
    the world stage”).
    Faculty Senate is readily distinguishable, for all of the same reasons the
    panel in that case distinguished it from Crosby. The Cuba Amendment creates
    more than a minor or incidental brush with federal law. Unlike in Faculty Senate,
    the Cuba Amendment absolutely involves Florida “select[ing] by name a foreign
    36
    Case: 12-13958       Date Filed: 05/06/2013      Page: 37 of 44
    country” -- Cuba -- and imposing an economic sanction on companies that do
    business there and even on companies that are only distantly affiliated with
    companies that do business there. Id. at 1210. The Cuba Amendment absolutely is
    intended to “prohibit” or “obstruct” domestic and foreign companies’ trade with
    Cuba. Id.; see also id. at 1209 (noting that “[t]he obvious idea” of the state law at
    issue in Crosby “was to reduce trade across-the-board with Burma”).                        And
    Florida’s $8 billion-a-year public contracting market absolutely is “big enough to
    be of serious concern on the world stage.” Id. at 1210 n.10. Indeed, it is four times
    the size of the public contracting market at issue in Crosby, and several foreign
    powers have already expressed serious concerns, even though the Amendment has
    never gone into operation.
    In short, Odebrecht has demonstrated a substantial likelihood of success on
    its claim that the Cuba Amendment is preempted by federal law. The Cuba
    Amendment conflicts with federal law in several ways, and undermines the full
    purposes and objectives of the extensive and nuanced federal Cuban sanctions
    regime. It therefore runs afoul of the Supremacy Clause, U.S. Const. art. VI, cl. 2,
    and must yield to federal law. 7
    7
    Because we hold that the Cuba Amendment is unconstitutional on grounds of conflict
    preemption, we have no occasion to separately address Odebrecht’s claims that the statute
    violates principles of field preemption, violates the Foreign Affairs Power, and violates the
    Foreign Commerce Clause. Cf. Crosby, 
    530 U.S. at
    374 n.8 (“Because our conclusion that the
    state Act conflicts with federal law is sufficient to affirm the judgment below, we decline to
    37
    Case: 12-13958        Date Filed: 05/06/2013        Page: 38 of 44
    III.
    In addition to showing a substantial likelihood of success on the merits,
    Odebrecht was also required to demonstrate that it would suffer irreparable harm
    absent an injunction, that the harm would exceed the harm suffered by the State if
    the injunction is issued, and that an injunction would not disserve the public
    interest. See Grizzle, 
    634 F.3d at 1320
    ; N. Am. Med., 
    522 F.3d at 1217
    .
    The Department says that Odebrecht failed on each count. It claims that
    Odebrecht has not successfully bid on a contract with FDOT in fifteen years and
    thus is not a serious contender in the bidding process, that Odebrecht has failed to
    identify with particularity how the Cuba Amendment has affected its ability to
    form partnerships and retain employees, that the people of Florida have a strong
    interest in the enforcement of the Cuba Amendment that outweighs any harm to
    Odebrecht, and that enforcement of the Cuba Amendment is in the public interest
    because it does not impose upon the federal government’s foreign policy towards
    Cuba. These arguments miss the mark.
    For starters, Odebrecht would suffer irreparable harm absent an injunction.
    “The basis of injunctive relief in the federal courts has always been irreparable
    harm and inadequacy of legal remedies.” Ne. Fla. Chapter of Ass’n of Gen.
    Contractors of Am. v. City of Jacksonville, 
    896 F.2d 1283
    , 1285 (11th Cir. 1990)
    speak to field preemption as a separate issue, or to pass on the First Circuit’s rulings addressing
    the foreign affairs power or the dormant Foreign Commerce Clause.” (citation omitted)).
    38
    Case: 12-13958     Date Filed: 05/06/2013    Page: 39 of 44
    (quoting Sampson v. Murray, 
    415 U.S. 61
    , 88 (1974)). The injury must be actual
    and imminent, not remote or speculative. 
    Id.
     Odebrecht has met this standard. It
    alleges three harms that are both actual and imminent: (1) the loss of its right to bid
    on public contracts, including the FDOT contracts that it has been prequalified to
    bid on, up to the sizable amount of $1.8 billion; (2) the loss of revenues and profits
    from contracts it can no longer bid for; and (3) interference with its ability to
    partner with other firms and retain employees. The substantial nature of the first
    harm cannot be overstated. Around 80% of Odebrecht’s revenues over the years
    have come from public contracts in the State of Florida, and 100% of its revenues
    in 2011 did so.
    FDOT’s only response is to say that Odebrecht has not successfully bid on a
    FDOT contract in fifteen years. The argument is flawed. First of all, FDOT does
    not explain why we should look only at FDOT contracts, as opposed to public
    contracts more broadly. The Cuba Amendment applies to all state agencies as well
    as all county and municipal governments in the State of Florida. See 
    Fla. Stat. § 287.135
    (1)(c), (2).     And the record demonstrates that Odebrecht is doing
    substantial business in the State of Florida. As we’ve noted, in 2011, 100% of
    Odebrecht’s revenues, amounting to over $200 million, were derived from state
    and local public contracts in Florida. Indeed, in the last ten years, Odebrecht and
    its joint venture partners have completed or are still in the process of completing
    39
    Case: 12-13958     Date Filed: 05/06/2013   Page: 40 of 44
    nine major contracts, worth a total of $3.3 billion, with Florida state agencies and
    local governments. One of those major contracts came as recently as May 2012,
    when Broward County awarded an Odebrecht joint venture a $226 million runway
    expansion project at the Fort Lauderdale Airport. There is no dispute that if the
    Cuba Amendment were in effect, Odebrecht would not have been able to bid on
    any of these contracts. In other words, if the Cuba Amendment were enforced
    against Odebrecht, almost its entire revenue stream would simply evaporate,
    causing Odebrecht substantial economic harm.
    Moreover, even if we limited our analysis to the Florida Department of
    Transportation alone, the record shows that Odebrecht intended to bid on or pursue
    several high-value FDOT contracts, and that FDOT had prequalified it to do so, up
    to $1.8 billion. The contracts Odebrecht intended to bid on include an estimated-
    $265 million project on the Palmetto Expressway and an estimated-$870 million
    project on Interstate 75. Odebrecht’s loss of an opportunity to bid on contracts like
    these is itself an injury, although Odebrecht is not assured of actually winning any
    given contract. As the Supreme Court has recognized in the context of standing to
    bring an equal protection challenge, “the ‘injury in fact’ is the inability to compete
    on an equal footing in the bidding process, not the loss of a contract.” Ne. Fla.
    Chapter of Associated Gen. Contractors of Am. v. City of Jacksonville, 
    508 U.S. 656
    , 666 (1993); accord 
    id.
     (“To establish standing, therefore, a party . . . need
    40
    Case: 12-13958   Date Filed: 05/06/2013   Page: 41 of 44
    only demonstrate that it is able and ready to bid on contracts and that a
    discriminatory policy prevents it from doing so on an equal basis.”). Although it
    arose in a slightly different context, we find the Supreme Court’s reasoning
    instructive.   Odebrecht’s intent and ability to bid on FDOT and other public
    contracts are neither speculative nor remote, Odebrecht would be harmed by the
    loss of an opportunity to bid on these contracts, and thus, even if we artificially
    limited our focus to the Florida Department of Transportation alone, Odebrecht
    still would be actually injured if the Cuba Amendment were to go into effect.
    These harms to Odebrecht absent an injunction are not only actual and
    imminent, they are also irreparable. Odebrecht has no monetary recourse against a
    state agency like FDOT because of the Eleventh Amendment. “[A]bsent waiver by
    the State or valid congressional override, the Eleventh Amendment bars a damages
    action against a State in federal court.” Kentucky v. Graham, 
    473 U.S. 159
    , 169
    (1985).   This includes damages claims against State officials in their official
    capacity. 
    Id.
     It is also clear that there has been no waiver or congressional
    override; indeed, the Supreme Court “has held that § 1983 was not intended to
    abrogate a State’s Eleventh Amendment immunity.” Id. at 169 n.17 (citing Quern
    v. Jordan, 
    440 U.S. 332
     (1979); Edelman v. Jordan, 
    415 U.S. 651
     (1974)). Ex
    Parte Young suits like the one brought here have never been held to permit
    retrospective monetary damages. See Fla. Ass’n of Rehabilitation Facilities, Inc.
    41
    Case: 12-13958    Date Filed: 05/06/2013   Page: 42 of 44
    v. Fla. Dep’t of Health & Rehabilitative Servs., 
    225 F.3d 1208
    , 1220 (11th Cir.
    2000) (“[T]he Eleventh Amendment does not generally prohibit suits against state
    officials in federal court seeking only prospective injunctive or declaratory relief,
    but bars suits seeking retrospective relief such as restitution or damages.”). In the
    context of preliminary injunctions, numerous courts have held that the inability to
    recover monetary damages because of sovereign immunity renders the harm
    suffered irreparable. See, e.g., Chamber of Commerce v. Edmondson, 
    594 F.3d 742
    , 770-71 (10th Cir. 2010) (“Imposition of monetary damages that cannot later
    be recovered for reasons such as sovereign immunity constitutes irreparable
    injury.”); Iowa Utils. Bd. v. FCC, 
    109 F.3d 418
    , 426 (8th Cir. 1996) (“The threat of
    unrecoverable economic loss . . . qualif[ies] as irreparable harm.”); ABC Charters,
    Inc. v. Bronson, 
    591 F. Supp. 2d 1272
    , 1310 (S.D. Fla. 2008) (“In the case at bar,
    Plaintiffs face serious economic harm as a result of the Travel Act Amendments
    and cannot sue the state of Florida for damages. Therefore, this harm is irreparable
    as a matter of law.”).
    The other equitable requirements are easily satisfied.      Odebrecht would
    suffer substantial injury in the loss of its ability to bid on state and local public
    contracts throughout Florida if the Cuba Amendment were to go into effect. On
    the flip side, the State is not harmed much, if at all, by the injunction. Indeed, an
    injunction against enforcement of the Cuba Amendment allows for greater
    42
    Case: 12-13958     Date Filed: 05/06/2013   Page: 43 of 44
    competition in bidding, which decreases the State’s overall costs. The only harm
    to the State is the more nebulous, not easily quantified harm of being prevented
    from enforcing one of its laws. That harm is present every time the validity of a
    state law is challenged, and it is far outweighed by the economic harm to
    Odebrecht and other companies that would be prevented from bidding on public
    contracts in Florida were the Cuba Amendment to go into effect.
    Finally, and relatedly, the State’s alleged harm is all the more ephemeral
    because the public has no interest in the enforcement of what is very likely an
    unconstitutional statute. As a panel of this Court recently explained, “[f]rustration
    of federal statutes and prerogatives are not in the public interest, and we discern no
    harm from the state’s nonenforcement of invalid legislation.” United States v.
    Alabama, 
    691 F.3d 1269
    , 1301 (11th Cir. 2012). In short, the injunction did not
    disserve the public interest.
    We have little difficulty concluding that Odebrecht has demonstrated a
    substantial likelihood of success on its claim that the Cuba Amendment is
    preempted by the extensive federal Cuban sanctions regime. The Amendment
    reaches far beyond the federal law in numerous ways and undermines the
    President’s exercise of the discretion afforded him by Congress to direct our
    Nation’s economic policy towards Cuba. In addition, the equities strongly favor a
    preliminary injunction prohibiting the enforcement of the Cuba Amendment.
    43
    Case: 12-13958   Date Filed: 05/06/2013   Page: 44 of 44
    AFFIRMED.
    44
    

Document Info

Docket Number: 12-13958

Citation Numbers: 715 F.3d 1268

Filed Date: 5/6/2013

Precedential Status: Precedential

Modified Date: 1/12/2023

Authorities (25)

Chamber of Commerce of United States v. Edmondson , 594 F.3d 742 ( 2010 )

Grizzle v. Kemp , 634 F.3d 1314 ( 2011 )

North American Medical Corp. v. Axiom Worldwide, Inc. , 522 F.3d 1211 ( 2008 )

SEC v. Unique Financial Concepts , 196 F.3d 1195 ( 1999 )

florida-association-of-rehabilitation-facilities-inc-united-cerebral , 225 F.3d 1208 ( 2000 )

northeastern-florida-chapter-of-the-association-of-general-contractors-of , 896 F.2d 1283 ( 1990 )

Faculty Senate of Florida International University v. Winn , 616 F.3d 1206 ( 2010 )

American Civil Liberties Union of Florida, Inc. v. Miami-... , 557 F.3d 1177 ( 2009 )

iowa-utilities-board-v-federal-communications-commission-united-states-of , 109 F.3d 418 ( 1996 )

Hines v. Davidowitz , 61 S. Ct. 399 ( 1941 )

Florida Lime & Avocado Growers, Inc. v. Paul , 83 S. Ct. 1210 ( 1963 )

United States v. Curtiss-Wright Export Corp. , 57 S. Ct. 216 ( 1936 )

Regan v. Wald , 104 S. Ct. 3026 ( 1984 )

ABC Charters, Inc. v. Bronson , 591 F. Supp. 2d 1272 ( 2008 )

Quern v. Jordan , 99 S. Ct. 1139 ( 1979 )

Sampson v. Murray , 94 S. Ct. 937 ( 1974 )

Edelman v. Jordan , 94 S. Ct. 1347 ( 1974 )

Northeastern Florida Chapter of the Associated General ... , 113 S. Ct. 2297 ( 1993 )

Crosby v. National Foreign Trade Council , 120 S. Ct. 2288 ( 2000 )

Arizona v. United States , 132 S. Ct. 2492 ( 2012 )

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