CVS Pharmacy, Inc. v. Lavin ( 2020 )


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  •           United States Court of Appeals
    For the First Circuit
    No. 19-1638
    CVS PHARMACY, INC.,
    Plaintiff, Appellee,
    v.
    JOHN LAVIN,
    Defendant, Appellant.
    APPEAL FROM THE UNITED STATES DISTRICT COURT
    FOR THE DISTRICT OF RHODE ISLAND
    [Hon. John J. McConnell, Jr., U.S. District Judge]
    Before
    Lynch, Selya, and Lipez,
    Circuit Judges.
    John J. Cotter, with whom Jennifer J. Nagle and K&L Gates LLP
    were on brief, for appellant.
    Michael L. Rosen, with whom Richard G. Baldwin, Allison L.
    Anderson, and Foley Hoag LLP were on brief, for appellee.
    February 28, 2020
    LIPEZ, Circuit Judge.          After working for nearly three
    decades    at    plaintiff-appellee       CVS     Pharmacy,        Inc.,    defendant-
    appellant John Lavin accepted a new position at PillPack LLC, a
    direct competitor of CVS.           But Lavin never actually started that
    job.   After obtaining information about Lavin's new role, CVS sued
    Lavin, seeking to enforce a covenant not to compete (the "covenant"
    or the "Agreement") included in a Restrictive Covenant Agreement
    ("RCA") that Lavin signed in 2017.                     Finding that Lavin's new
    position      would    violate    the   covenant       and   concluding      that    the
    covenant was reasonable, the district court entered a preliminary
    injunction enjoining Lavin from working at PillPack for eighteen
    months,    the       duration    specified   in    the       covenant.        In    this
    interlocutory        appeal,    Lavin   argues    that       the   covenant    is    not
    reasonable and that the preliminary injunction, therefore, should
    not have been granted.            Although our reasoning differs somewhat
    from   that     of    the   district    court,    we    affirm     the     entry    of   a
    preliminary injunction enforcing the covenant not to compete.
    - 2 -
    I.
    A.   Factual Background1
    1.      CVS Caremark's Business
    CVS operates CVS Caremark, one of the country's largest
    pharmacy    benefit   managers     ("PBMs").        PBMs   sell   prescription-
    management     services     to    entities    providing      prescription-drug
    coverage to their members.         These entities -- known as payers --
    include     employers,    insurance    companies,      and    unions.     PBMs
    negotiate     on   behalf    of    payers    with    pharmacies     to   secure
    reimbursement rates for prescription drugs.                They also establish
    pharmacy networks for payers, premised on each payer's individual
    needs and preferences; furnish an array of administrative services
    (such as claims adjudication and eligibility determinations); and
    procure bulk discounts and rebates directly from pharmaceutical
    manufacturers.     For its part, CVS Caremark offers its own mail-
    order pharmacy services to certain payers as clients.
    CVS operates other healthcare-related subsidiaries in
    addition to CVS Caremark, including a sprawling chain of retail
    pharmacies.     CVS has erected a firewall between CVS Caremark and
    its retail pharmacy subsidiary.            This firewall not only prevents
    1 "[W]e credit the undisputed facts presented below and adopt
    the district court's findings as to controverted matters to the
    extent they are supported by the record and not clearly erroneous."
    United Elec., Radio & Mach. Workers of Am. v. 163 Pleasant St.
    Corp., 
    960 F.2d 1080
    , 1083 (1st Cir. 1992).
    - 3 -
    CVS Caremark's employees from accessing the prices that CVS's
    retail pharmacies negotiate with other PBMs but also prevents
    employees of CVS's retail pharmacies from accessing the prices
    that CVS Caremark negotiates with other retail pharmacies.
    2.    Lavin's Employment at CVS
    After his almost three decades at CVS Caremark and its
    predecessor,    Lavin    became    Senior     Vice   President     for   Provider
    Network Services in 2010.          In this role, he oversaw a team of
    approximately    250    people    and   was   responsible    for    negotiating
    pricing contracts with retail pharmacies, auditing pharmacies, and
    setting up pharmacy networks for payers.             He also participated in
    regular underwriting calls for the contracts that CVS Caremark
    negotiated with its payer clients.            In light of these duties, he
    became intimately familiar with the prices and terms of CVS
    Caremark's deals with both retail pharmacies and payers.
    Lavin was also involved in certain strategic initiatives
    undertaken by CVS Caremark.           For instance, he assisted with the
    company's strategy for contracting with mail-in retail pharmacies
    ("MIRs"), which fill prescriptions by mail.            This project included
    developing     strategies     about     how   best    to   differentiate     CVS
    Caremark's mail-based services from those offered by MIRs.                    He
    helped    formulate     CVS   Caremark's      strategy     for   the     upcoming
    contracting cycle and create novel pharmacy reimbursement and
    pricing models. Each year, he attended several executive committee
    - 4 -
    meetings that covered an array of topics ranging from revenue and
    pricing to major client accounts and regulatory impacts.
    3.     Noncompetition Agreement
    At four points during his tenure as a senior vice
    president at CVS Caremark -- in 2011, 2012, 2014, and 2017 -- CVS
    required Lavin to sign an RCA.        Each RCA contained noncompetition,
    nonsolicitation, and nondisclosure covenants.            Each time Lavin
    signed an RCA, he was awarded CVS stock.
    The 2017 RCA, executed in exchange for a stock award
    worth $157,500, is the centerpiece of this appeal.            The covenant
    not to compete contained therein bars Lavin, for eighteen months
    after    the    termination   of   his   employment,   from   "directly   or
    indirectly . . . engag[ing] in Competition" anywhere in the United
    States that CVS operates.          The covenant in the 2017 RCA defines
    "Competition" as:
    [P]roviding services to a Competitor of the
    Corporation [CVS] . . . that:      (i) are the
    same or similar in function or purpose to the
    services I [Lavin] provided to the Corporation
    at any time during the last two years of my
    employment by the Corporation; or (ii) will
    likely   result    in   the    disclosure   of
    Confidential Information to a Competitor or
    the use of Confidential Information on behalf
    of a Competitor.
    "Competitor" is defined, in turn, as:
    [A]ny person, corporation or other entity that
    competes with one or more of the business
    offerings of the Corporation[.] . . . [T]he
    Corporation's business offerings include:
    - 5 -
    (i) pharmacy benefits management ("PBM")
    . . .; (ii) retail, which includes the sale of
    prescription      drugs,       over-the-counter
    medications, [and other products and services
    sold by CVS's retail pharmacies] ("Retail");
    (iii) retail health clinics ("MinuteClinic");
    (iv) the provision of [various products and
    services] to long-term care facilities, other
    healthcare service providers and recipients of
    services from such facilities ("Long-Term
    Care"); (v) the provision of prescription
    infusion    drugs    and    related    services
    ("Infusion"); and (vi) any other business in
    which   [the]   Corporation   is   engaged   or
    imminently will be engaged.
    . . . .
    The Parties acknowledge that . . . an entity
    will be considered a Competitor if it provides
    products or services competitive with the
    products   and  services   provided   by   the
    Corporation within the last two years of my
    employment.
    I   agree    to   this    enterprise-wide
    definition of non-competition which may
    prevent me from providing services to any of
    the Corporation's PBM, Retail, MinuteClinic,
    Long-Term Care and Infusion Competitors or any
    combination thereof . . . .
    This definition of "Competition" and the eighteen-month
    noncompetition period appear in all four of the RCAs that Lavin
    signed.    However, the definition of "Competitor" expanded over
    time.     The 2011 and 2012 RCAs limited "Competitors" to other
    companies providing PBM services.           The 2014 RCA expanded this
    definition to include retail pharmacies and health clinics, as
    well as any other entity that "provides products or services
    competitive   with   the   products   and    services   provided   by   the
    - 6 -
    Corporation within the last two years" of Lavin's employment.                  By
    2017, as stated above, the definition of "Competitor" included
    companies providing services to long-term care facilities and
    prescription infusion drugs.
    4.        Lavin's New Job at PillPack
    In   November   of   2018,   Lavin   began    discussions   with
    PillPack about possible employment.              PillPack is an online retail
    pharmacy founded in 2013 and wholly owned by Amazon.com, Inc.
    PillPack aspires to create a new model of providing prescription
    drugs        to    patients.      Previously,     Lavin   led    CVS   Caremark's
    development of a strategy for determining whether and under what
    terms to contract with PillPack, which is now enrolled in CVS
    Caremark's pharmacy network.               Neither PillPack nor Amazon.com
    operates a traditional PBM business.
    Lavin accepted employment at PillPack on March 29, 2019
    and gave CVS his two-week notice on April 8, 2019.                     In his new
    position, he will be responsible for negotiating with PBMs and
    payers.2          Moreover, PillPack's chief executive officer ("CEO")
    stated that he expects Lavin to "contribute significantly to
    2
    During some stages of the litigation, Lavin asserted that
    his new job will require him to negotiate only with PBMs. The
    district court found this assertion too modest and determined that
    Lavin's responsibilities also will include negotiating with
    payers. See CVS Pharmacy, Inc. v. Lavin, 
    384 F. Supp. 3d 227
    ,
    230, 234 (D.R.I. 2019).    Lavin does not challenge this factual
    finding on appeal.
    - 7 -
    [PillPack's] procurement efforts . . . and help [PillPack] develop
    a long term disruptive strategy."               CVS Pharmacy, Inc. v. Lavin,
    
    384 F. Supp. 3d 227
    , 230 (D.R.I. 2019) (alteration in original).
    Lavin and PillPack have agreed that he will be recused, at least
    for some period of time, from any discussions or work involving
    CVS    Caremark    or   its    clients.         Those    projects    will   be   the
    responsibility of PillPack's CEO, to whom Lavin will report.
    B.     Procedural History
    After       requesting      information        about     Lavin's     new
    employment, CVS filed a diversity suit against Lavin in the United
    States District Court for the District of Rhode Island, seeking to
    enforce the covenant not to compete contained in the 2017 RCA.
    The district court entered a temporary restraining order barring
    Lavin    from     either      working    for     or     disclosing   confidential
    information to PillPack.         After limited discovery, conducted on an
    expedited basis, CVS moved for a preliminary injunction.
    On June 18, 2019, the district court granted CVS's
    motion. See 
    id. at 238.
    The court concluded that Lavin's proposed
    work for PillPack would violate the terms of the covenant not to
    compete.     See 
    id. at 233-36.
               Moreover, the court found the
    covenant reasonable and, therefore, enforceable under Rhode Island
    law.    See 
    id. at 236-37.
            Lavin filed this interlocutory appeal
    challenging the entry of the preliminary injunction.
    - 8 -
    II.
    When       assessing     whether     to   grant   a     preliminary
    injunction, a trial court must consider four factors: "the movant's
    likelihood of success on the merits"; "whether and to what extent
    the   movant   will    suffer     irreparable   harm"   in   the   absence   of
    injunctive relief; "the balance of [relative] hardships," that is,
    the hardship to the nonmovant if enjoined as opposed to the
    hardship to the movant if no injunction issues; and "the effect,
    if any, that an injunction [or the lack of one] may have on the
    public interest."       See Corp. Techs., Inc. v. Harnett, 
    731 F.3d 6
    ,
    9 (1st Cir. 2013).3       In his interlocutory appeal, Lavin has made
    no arguments concerning the second, third, and fourth factors,
    which the district court concluded supported the entry of a
    preliminary injunction.         See CVS 
    Pharmacy, 384 F. Supp. 3d at 237
    -
    38.   Thus, we focus only on the first: CVS's likelihood of success
    on the merits.    This factor weighs most heavily in the preliminary
    injunction analysis. See Ross-Simons of Warwick, Inc. v. Baccarat,
    Inc., 
    102 F.3d 12
    , 16 (1st Cir. 1996).
    When reviewing a district court's entry of a preliminary
    injunction, we examine legal questions de novo, findings of fact
    for clear error, and the balancing of the four factors for abuse
    3Because "the parties have not suggested that state law
    supplies meaningfully different criteria," we will use the federal
    preliminary injunction standard in this diversity case. See Lanier
    Prof'l Servs., Inc. v. Ricci, 
    192 F.3d 1
    , 3 (1st Cir. 1999).
    - 9 -
    of discretion.      See Corp. 
    Techs., 731 F.3d at 10
    .         Although review
    for abuse of discretion demands a degree of deference to the
    district court, we have found district courts to have abused their
    discretion    by    making    "a   material    error   of    law,"   see   
    id., "ignor[ing] pertinent
         elements   deserving     significant    weight,
    consider[ing]      improper    criteria,      or,   though    assessing    all
    appropriate and no inappropriate factors, plainly err[ing] in
    balancing them," 
    Ross-Simons, 102 F.3d at 16
    .
    III.
    A.   Enforceability of Covenants Not to Compete
    Under Rhode Island law,4 a party seeking to enforce a
    covenant not to compete must first establish three threshold
    requirements: (1) the covenant "is ancillary to an otherwise valid
    transaction or relationship, such as an employment contract"; (2)
    the covenant "is supported by adequate consideration"; and (3) the
    covenant is designed to protect a "legitimate interest" of the
    employer.    Durapin, Inc. v. Am. Prods., Inc., 
    559 A.2d 1051
    , 1053
    (R.I. 1989).       The district court concluded that these threshold
    4 To evaluate the likelihood of success on the merits in a
    diversity case, we look to state law for the substantive rules of
    decision. See Erie R.R. Co. v. Tompkins, 
    304 U.S. 64
    , 78 (1938);
    Crellin Techs., Inc. v. Equipmentlease Corp., 
    18 F.3d 1
    , 4 (1st
    Cir. 1994). When the parties have agreed about what law applies,
    a federal court sitting in diversity need not engage in an
    independent choice-of-law analysis.    See Borden v. Paul Revere
    Life Ins. Co., 
    935 F.2d 370
    , 375 (1st Cir. 1991). Thus, we will
    apply Rhode Island law, per the parties' agreement in the 2017 RCA
    and in the district court.
    - 10 -
    requirements were met, including that the covenant was designed to
    protect CVS's legitimate interest in securing its confidential
    information.     CVS 
    Pharmacy, 384 F. Supp. 3d at 236-37
    .               Lavin does
    not challenge this determination on appeal.
    Rather, Lavin focuses his argument on the reasonableness
    of the 2017 covenant.        In Rhode Island, "covenants not to compete
    are disfavored and subject to strict judicial scrutiny."                     Cranston
    Print    Works   Co.   v.   Pothier,     
    848 A.2d 213
    ,   219    (R.I.    2004).
    Accordingly, such covenants "will be enforced as written only if
    the contract is reasonable and does not extend beyond what is
    apparently necessary for the protection of those in whose favor it
    runs."     
    Durapin, 559 A.2d at 1053
    .                  The reasonableness of a
    covenant    depends    on    factors     such   as     whether   it    is    narrowly
    tailored; whether its scope is reasonably limited in activity,
    geography, and time; whether the hardship to the employee outweighs
    the employer's need for protection; and whether enforcement of the
    covenant is likely to harm the public interest.                  See R.J. Carbone
    Co. v. Regan, 
    582 F. Supp. 2d 220
    , 225 (D.R.I. 2008).                       Whether a
    covenant is reasonable is a question of law.               
    Durapin, 559 A.2d at 1053
    .    If a covenant is unreasonable, a court may nevertheless
    modify and enforce the covenant, under Rhode Island's partial
    enforcement      doctrine,    to   the    extent       reasonably     necessary    to
    protect the employer's legitimate interests, so long as there is
    - 11 -
    "no evidence of bad faith or deliberate overreaching on the part
    of the promisee." 
    Id. at 1058.
    Lavin insists that the covenant here is unreasonable and
    therefore not enforceable because its definition of "Competition,"
    which incorporates its expansive definition of "Competitor," is
    overly broad.    While Lavin does not contest that his new position
    at PillPack falls within the scope of the covenant's prohibited
    activities, or that PillPack qualifies as a Competitor under the
    terms of the Agreement, he contends that, because the covenant
    sweeps more broadly than necessary to protect CVS's confidential
    information, the covenant as a whole is unreasonable and, hence,
    unenforceable.      In       other   words,     Lavin     asserts   that   the
    reasonableness of the covenant must be assessed facially.
    CVS   urges   a    different       view   of   the   reasonableness
    inquiry.   While CVS does appear at points in its brief to defend
    the covenant as facially reasonable, it ultimately urges us to
    analyze reasonableness in light of the district court's factual
    findings about the ways in which Lavin might violate the covenant.
    CVS contends that, because Rhode Island law requires courts to
    consider the particular facts of a case, courts cannot consider
    the language of restrictive covenants in a vacuum or rely on
    hypothetical employment constraints to assess whether a particular
    covenant imposes a reasonable restriction.                Instead, the court
    should take an "as-applied" approach to assessing reasonableness:
    - 12 -
    the court should consider only whether its enforcement in a
    particular instance -- here, to prevent Lavin from starting his
    job at PillPack -- is reasonable.     Even if the covenant may sweep
    more broadly than necessary to protect CVS's legitimate interests,
    that is an issue for another day under CVS's view of the law.         As
    it turns out, both parties' interpretations of Rhode Island law
    draw support from the applicable precedent and secondary sources
    embraced by the Rhode Island Supreme Court.
    B.    Two Views of Reasonableness under Rhode Island Law
    The Rhode Island Supreme Court has made clear that the
    reasonableness of a covenant is fact-specific: "[w]hen considering
    the validity of a noncompetition agreement, the crucial issue is
    reasonableness, and that test is dependent upon the particular
    circumstances surrounding the agreement."        
    Durapin, 559 A.2d at 1053
    (citing Max Garelick, Inc. v. Leonardo, 
    250 A.2d 354
    , 356-57
    (R.I. 1969)). The Second Restatement of Contracts, which the Rhode
    Island Supreme Court has adopted, see Cranston Print 
    Works, 848 A.2d at 219
    ; see also Nestle Food Co. v. Miller, 
    836 F. Supp. 69
    ,
    73-74 (D.R.I. 1993), also affirms that "[w]hat limits as to
    activity, geographical area, and time [in a restrictive covenant]
    are   appropriate   in   a   particular   case   depends   on   all   the
    circumstances," Restatement (Second) of Contracts § 188, cmt. d
    (Am. Law Inst. 1981).
    - 13 -
    However, it is not clear whether an assessment of "the
    particular circumstances" means that Rhode Island law calls for a
    facial review of a covenant, as Lavin contends, or as applied, as
    CVS argues.     On the one hand, Rhode Island's policy concerns about
    restrictive covenants weigh against a case-specific approach.
    See, e.g., Cranston Print 
    Works, 848 A.2d at 219
    (stating that
    covenants not to compete are "disfavored" and subject to "strict
    judicial scrutiny"); see also 6 Williston on Contracts § 13:4 (4th
    ed. 2019) (describing concerns that restrictive covenants can be
    "oppressive" and injurious to the public interest).                          As Lavin
    points   out,      covenants         preventing    free     job   movement   diminish
    competition and can influence employees' decisions even before an
    employer seeks to enforce a covenant in court.                         This general
    skepticism suggests that courts should engage in facial review of
    covenants.      Such review would incentivize the drafting of narrow
    noncompetition       agreements         and   combat   the    negative     impact   of
    sweeping covenants.
    Facial review is also consistent with the Rhode Island
    Supreme Court's repeated formulation of the reasonableness inquiry
    as focused on the agreement as a whole.                See, e.g., Cranston Print
    
    Works, 848 A.2d at 219
    (noting that the party seeking enforcement
    must show that "the contract is reasonable" (emphasis added));
    
    Durapin, 559 A.2d at 1053
      (stating       that    assessing      the
    reasonableness       of     a    covenant         depends    on     "the   particular
    - 14 -
    circumstances     surrounding    the    agreement"     (emphasis    added));
    Oakdale Mfg. Co. v. Garst, 
    28 A. 973
    , 974 (R.I. 1894) (stating
    that "[t]he test [of reasonableness] is to be applied according to
    the circumstances of the contract").
    On the other hand, Rhode Island courts have, at times,
    used   language    that   emphasizes     the   importance    of    assessing
    reasonableness based on the facts of a given case, echoing a
    traditional as-applied test.      See, e.g., Mento v. Lanni, 
    262 A.2d 839
    , 841-42 (R.I. 1970) (noting that "since we are dealing with
    the concept of reasonableness, each case must be judged on its own
    facts" (emphases added)).       In Mento, for instance, the defendant,
    Lanni, sold the plaintiff, Mento, a barber shop and, in the bill
    of sale, agreed "not [to] open another barber shop under the same
    name or any other name within a two-mile radius of the shop."            
    Id. at 839.
       Although Lanni continuously operated a barber shop in
    Providence after the sale, it was only after five years that he
    opened a shop somewhere less than two miles from the original
    location, in violation of the agreement.         
    Id. When Mento
    sued to
    enforce the agreement, the Rhode Island Supreme Court considered,
    in   assessing    the   agreement's    reasonableness,    numerous    facts,
    including the number of customers Mento claimed he had lost after
    Lanni opened his shop and that Mento had himself seen his business
    grow from one to three barbers.        
    Id. at 842.
      Based on these facts,
    the court concluded that enforcing the agreement after this much
    - 15 -
    time had passed was unreasonable, even though the agreement itself
    included no temporal restriction.    
    Id. at 842-43.
    The Corbin on Contracts treatise, which the Rhode Island
    Supreme Court has cited favorably, see 
    Durapin, 559 A.2d at 1059
    ,
    arguably supports such an as-applied approach.      After noting that
    courts often have difficulty determining the precise bounds of a
    reasonable restriction, the treatise explains that making such a
    determination is often unnecessary because "[t]he question before
    the court tends usually to be whether a restriction against what
    the defendant has done in fact or is threatening to do would be a
    reasonable and valid restriction."   15 Corbin on Contracts § 80.26
    (2019).   Accordingly,   "[t]he   court   should   always   permit   the
    plaintiff to show the actual extent of the protectable interest
    that is involved and that the defendant has committed a breach
    within that extent."5    
    Id. (emphasis added).
        In this case, for
    instance, the covenant at issue includes six kinds of Competitors,
    only two of which were relevant to the district court's conclusion
    that PillPack was a Competitor.   Under a facial review, CVS would
    5  We acknowledge, as Judge Selya points out in his
    concurrence, that this passage appears in a section of the treatise
    entitled "Partial Enforcement of Restrictive Covenants."         15
    Corbin on Contracts § 80.26. However, the language in the passage
    suggests that the described approach is the way that courts should
    always approach their analysis of a covenant's reasonableness.
    Whether, by doing so, courts are, in fact, conducting a partial
    enforcement analysis, as Judge Selya contends, we think unclear
    both from the treatise and the caselaw.
    - 16 -
    nevertheless need to justify the breadth of that definition, even
    though that broad inquiry would have little to do with the actual
    controversy between the parties.        The as-applied approach avoids
    that inefficient mismatch.
    Indeed, we see the potential unwieldiness of the facial
    approach as strong support for CVS's view of the reasonableness
    inquiry.     By their nature, lawsuits to enforce covenants not to
    compete must be decided quickly and, often, as here, at the
    preliminary injunction stage.       Engaging in a meaningful facial
    review of an agreement would often require extensive discovery.
    For this reason, as the Corbin treatise suggests, the as-applied
    approach may be more workable for courts.
    C.    The Reasonableness of CVS's Agreement
    As the discussion above reveals, we are presented with
    two compelling views of Rhode Island law, which reflect a tension
    between the state's policy concerns, addressed by the facial
    approach, and the practical benefits of the as-applied approach.
    Typically, when a federal court is confronted with an unresolved
    question of state law, our job is to "ascertain the rule the state
    court would most likely follow under the circumstances."      Blinzler
    v. Marriott Int'l, Inc., 
    81 F.3d 1148
    , 1151 (1st Cir. 1996).        We
    may   look    to   "analogous   state   court   decisions,   persuasive
    adjudications by courts of sister states, learned treatises, and
    public policy considerations identified in state decisional law"
    - 17 -
    for guidance.     
    Id. But we
    must "take care not to extend state law
    beyond its well-marked boundaries in an area . . . that is
    quintessentially the province of state courts."                  Markham v. Fay,
    
    74 F.3d 1347
    , 1356 (1st Cir. 1996).
    Here, however, we need not take a position on which
    understanding of Rhode Island law is correct, because, under either
    analytical framework, as we explain, the outcome would be the same.
    1.     As-Applied Review
    Before assessing whether the Agreement was reasonable,
    the district court had to consider whether Lavin's new job at
    PillPack fell within the Agreement's prohibited activities.                      The
    district court concluded that it did.               CVS Pharmacy, 
    384 F. Supp. 3d
    at 236.      In making this threshold determination, the district
    court made numerous factual findings, including that "it is highly
    likely   that    Mr.    Lavin's    new    employment     will    result     in   the
    disclosure of Confidential Information" to PillPack, "a Competitor
    in the industry."        
    Id. Under Rhode
    Island law, "a business's
    confidential     information      .   .   .   may   qualify     as   a   legitimate
    interest" that a noncompetition agreement can protect.                   Astro-Med,
    Inc. v. Nihon Kohden Am., Inc., 
    591 F.3d 1
    , 17 (1st Cir. 2009).
    Lavin contends that there are narrower means to protect
    CVS's interest in its confidential information than preventing him
    from assuming the position at all.            Specifically, Lavin points out
    that the 2017 RCA also contains nondisclosure and nonsolicitation
    - 18 -
    provisions.      He argues that these provisions suffice to protect
    CVS's confidential information from PillPack.             Thus, he contends,
    the Agreement as applied even to his specific position at PillPack
    is   unreasonable    because    barring     Lavin's    employment       entirely,
    rather than imposing other restrictions on what he can do at
    PillPack, is too broad a restraint.
    We disagree.       The district court's factual findings show
    that Lavin has extensive knowledge of CVS Caremark's strategic
    initiatives and detailed information about its contracts with
    retail pharmacies and payers.        It strains credulity to think that
    a top-echelon executive like Lavin could develop a strategy for
    PillPack without dipping into this knowledge.                  Indeed, as the
    district court found, see CVS Pharmacy, 
    384 F. Supp. 3d
    at 230,
    PillPack hired Lavin in part to help develop tactics to disrupt
    the industry, a role that he is suited to perform chiefly because
    of his knowledge of strategic initiatives developed by a major
    industry player.
    For      similar      reasons,         PillPack's     and      Lavin's
    representations     that   Lavin   will     not    participate   in     any   work
    involving CVS Caremark or its clients are not sufficient to protect
    CVS's confidential information, such that enforcing the Agreement
    here would be unreasonable.        As the district court found, in his
    new position, Lavin would report directly to PillPack's CEO, 
    id., who, in
    turn, would be overseeing work related to CVS.                 PillPack's
    - 19 -
    CEO has indicated that the two would communicate openly about
    Lavin's strategy for negotiating with PBMs other than CVS, Lavin's
    "primary responsibility" at PillPack.            
    Id. at 234.
         Thus, the
    confidential     information    Lavin   gained   from   his   years   at   CVS
    Caremark,    which    would     inevitably   inform     his    strategy     in
    negotiating with other PBMs, would indirectly inform the CEO's
    similar negotiations with CVS Caremark.6
    For these reasons, we conclude that, under an as-applied
    approach, enforcing the Agreement to bar Lavin from working at
    PillPack is reasonable.        The narrower means that Lavin has argued
    would protect CVS's confidential information are               insufficient
    based on the district court's unchallenged factual findings about
    Lavin's role at CVS and his new position at PillPack.
    2.    Facial Review and Partial Enforcement
    In granting the preliminary injunction for CVS, the
    district court took the facial approach and held that, as written,
    the Agreement was reasonable and, thus, enforceable.            
    Id. at 236-
    6 In his reply brief, Lavin also asserts that barring him from
    working for PillPack would impose an undue hardship upon him and,
    at the same time, offend the public's interest in a competitive
    pharmaceutical    industry,   factors    relevant   in    assessing
    reasonableness under Rhode Island law. See R.J. Carbone, 582 F.
    Supp. 2d at 225. Although Lavin made passing references in his
    opening brief to his inability to work, he did not develop this
    argument there, and it is therefore waived. See Lawless v. Steward
    Health Care Sys., LLC, 
    894 F.3d 9
    , 25 (1st Cir. 2018) (holding
    that arguments advanced for the first time in an appellant's reply
    brief are deemed waived).
    - 20 -
    37.   The court concluded that "[t]he non-competition provision in
    the Agreement is tailored to serve CVS's legitimate interest in
    protecting    its   Confidential    Information           and    is   reasonable     in
    duration and scope." 
    Id. In reaching
    this determination, it noted
    that "[t]he Agreement specifically and narrowly defines both what
    qualifies as 'Competition' and who qualifies as a 'Competitor' to
    protect its legitimate interests."            
    Id. at 237.
    We are not prepared, at this preliminary stage of the
    litigation, and on the record before us, to adopt the district
    court's conclusion that the Agreement is reasonable on its face.
    For   example,   CVS   has   not   explained        how    the    lengthy    list    of
    "Competitors" in the RCA meets the narrow-tailoring requirement of
    Rhode Island law.
    However, our analysis under this facial framework does
    not end simply because we decline to take a position on the
    Agreement's facial reasonableness.                 As explained above, Rhode
    Island has adopted the doctrine of partial enforcement, which
    permits the enforcement of overly broad covenants to the extent
    reasonable,    so   long   as   there   is    no    bad    faith      or   deliberate
    overreaching by the employer.           
    Durapin, 559 A.2d at 1058
    .                  The
    district court concluded that this case did not involve deliberate
    overreaching.       CVS    Pharmacy,    384    F.    Supp.       3d   at   237   n.9.7
    7Lavin disputes this finding on appeal.       But he has not
    identified any evidence that persuades us that the district court's
    - 21 -
    Therefore, even if Rhode Island does require a facial review of a
    covenant's terms, and even assuming CVS failed such a review here,
    we conclude that, pursuant to the partial enforcement doctrine, it
    is reasonable to enforce the Agreement to prevent Lavin from
    commencing his work at PillPack for the specified duration.           That
    is, even if the Agreement is facially overbroad, an assumption
    that we make here for the purpose of analysis, the doctrine of
    partial   enforcement   permits   us   to   "modify"   the   overly   broad
    Agreement and enforce it to the extent reasonable.               Here, we
    conclude that Lavin's new role at PillPack would fall within the
    bounds of activities prohibited by the Agreement, even assuming
    its scope needed to be reduced to make it reasonable.
    We acknowledge that we have found no Rhode Island cases
    that use the partial enforcement doctrine in this way.         Typically,
    courts interpreting Rhode Island law have used the doctrine to
    reduce a temporal or geographic restriction that a party is
    attempting to enforce but that a court concludes is unreasonable.
    See, e.g., Astro-Med, 
    Inc., 591 F.3d at 14-15
    ; R.J. Carbone 
    Co., 582 F. Supp. 2d at 225-26
    .   For instance, in R.J. Carbone Co., the
    defendant, Timothy Regan, who had worked as a salesman for Carbone,
    finding was clearly erroneous.      He simply points to earlier
    noncompetition agreements with fewer restrictions as evidence that
    CVS deliberately overreached in drafting the agreement at issue
    here. The bare fact of a broader agreement does not on its own
    prove overreaching.
    - 22 -
    a floral distributor, had signed a covenant "not to compete with
    Carbone for one year within 100 miles of Hartford, 
    Connecticut." 582 F. Supp. 2d at 222
    .    When Regan left Carbone, he went to work
    for another floral distributor and sold flowers to at least two of
    his previous customers from Carbone.       
    Id. at 222-23.
      Carbone sued
    to enforce the noncompetition agreement.        
    Id. at 223.
       Applying
    Rhode Island law, the district court concluded that, although the
    agreement was reasonable in its restriction on the kinds of
    activities Regan could perform and the time period for which the
    restriction would apply, the geographic scope was overly broad --
    the 100 mile radius unnecessarily included "potential customers to
    whom Regan never sold, and prior customers to whom he has not
    recently sold."     
    Id. at 226.
    Accordingly, the court used the doctrine of partial
    enforcement to reduce the unreasonable geographic limit.         
    Id. at 226-27.
      It issued an injunction tailored to prevent Regan from
    soliciting current Carbone customers with whom he had worked in
    his assigned sales territory, rather than with a general geographic
    limitation.   
    Id. Stated more
    generally, the court refused to
    enforce the full scope of the agreement, as Carbone sought, and
    instead partially enforced it, delivering only some of the relief
    to Carbone that it requested by actually modifying the terms of
    the agreement.
    - 23 -
    The case before us does not fit this model and, thus,
    the applicability of the partial enforcement doctrine is less
    straightforward.     Unlike in Carbone, we are not "modifying" or
    narrowing a term of the Agreement so that it can be enforced
    reasonably.     Nor are we delivering only part of the relief CVS
    seeks.     Rather, we are using the partial enforcement doctrine to
    conclude    that   any   potentially   unreasonable   aspects   of   the
    Agreement do not prevent CVS from winning the full relief it seeks
    based on the narrowest aspects of the Agreement as written.8
    Strikingly, when used in this way, the partial enforcement doctrine
    mirrors an as-applied approach.9
    8  For instance, even if we were to hold that the full
    definition   of   "Competitor"   is   unreasonable,   the   partial
    enforcement doctrine would allow us to strike the offending aspects
    of the definition and retain those that are reasonable.         The
    remainder of a modified definition would include PillPack, given
    its direct competition with the division of CVS in which Lavin
    worked.
    9 Judge Selya criticizes the as-applied approach because he
    thinks its similarity in this case to the partial enforcement
    analysis suggests that the two are mutually exclusive.      In his
    view, this means that the as-applied approach cannot be correct
    because that approach would render superfluous the doctrine of
    partial   enforcement   and   irrationally   do  away   with   its
    prerequisites -- a showing that the restrictive provision was not
    the result of bad faith or deliberate overreaching. Although in
    a much more circumscribed way, we think there could still be room
    for the application of the partial enforcement doctrine under the
    as-applied approach. For example, if the covenant at issue here
    precluded Lavin from engaging in Competition for ten years, rather
    than eighteen months, we might conclude that the lengthy temporal
    restriction makes the Agreement unreasonable, even using the as-
    applied approach. However, the partial enforcement doctrine would
    allow us to enforce the Agreement to prevent Lavin from taking his
    job but for less than the full ten years, as written in the
    - 24 -
    We are confident that using the partial enforcement
    doctrine in this way is consistent with the principles articulated
    in the Rhode Island cases that employ this doctrine -- that courts
    in equity should enforce agreements to the extent reasonable --
    such that CVS wins, even if Lavin is correct that reasonableness
    must be assessed facially.         Nonetheless, because we have found no
    cases using the doctrine as we have, we hesitate to conclude that
    this is the analytical framework -- rather than a straightforward
    as-applied approach -- that a Rhode Island court would employ if
    presented with a case of this kind.
    We recognize that, as we have undertaken them here, these
    two approaches look alike in many respects.            However, as we have
    suggested,    the   facial   and    as-applied   approaches    can   diverge
    significantly.       Typically,      facial   review   would   require   an
    exhaustive inquiry into the reasonableness of all aspects of an
    agreement, even those not directly at issue -- an inquiry we have
    omitted here only by assuming unreasonableness.           There is another
    significant distinction: the partial enforcement doctrine can be
    used only after a court confirms that there has been no bad faith
    Agreement.   That said, we do acknowledge that the as-applied
    approach would reduce the role of the partial enforcement doctrine
    and also permit employers to enforce covenants without first
    showing that a covenant is reasonable as a whole or, at a minimum,
    not the product of bad faith or overreaching.         As we have
    expressed, these policy concerns, as reflected in decisions of the
    Rhode Island Supreme Court, are what give us pause about embracing
    the as-applied approach outright.
    - 25 -
    or deliberate overreaching.     Although that consideration does not,
    as we explained, change the outcome in this case, it might in
    others.   Thus, we leave it to the Rhode Island courts to clarify
    which doctrinal framework is correct when, like here, a party seeks
    relief based on the narrowest aspects of a broad agreement.
    IV.
    For the reasons described above, we conclude that CVS is
    likely to succeed on the merits of its claim for injunctive relief,
    whether the trial court uses the as-applied or the facial approach
    in evaluating the reasonableness of the restrictive covenant at
    issue.    Because   this   is   the    only   factor   of   the   preliminary
    injunction framework that Lavin challenges in this interlocutory
    appeal, and because the district court concluded that the other
    factors counsel in favor of CVS, we affirm the district court's
    entry of a preliminary injunction.
    So ordered.
    -Concurring Opinions Follow-
    - 26 -
    LYNCH, Circuit Judge, concurring.          I join only those
    portions of Judge Lipez's opinion affirming the district court on
    the basis of what that opinion calls the "as applied" analysis.
    Rhode Island law requires that result.          I do not join and do not
    agree with those portions of the opinion purporting to find in
    Rhode Island law a "facial analysis" of non-compete agreements and
    the   opinion's   unprecedented    use     of   the   partial   enforcement
    doctrine.   If Rhode Island law is to be extended in either of those
    two ways, it is up to the Rhode Island courts or legislature to do
    so, and not the federal courts.          See Doe v. Trs. of Bos. Coll.,
    
    942 F.3d 527
    , 535 (1st Cir. 2019); Rared Manchester NH, LLC v.
    Rite Aid of N.H., Inc., 
    693 F.3d 48
    , 54 (1st Cir. 2012) ("[W]e
    ought not 'stretch state precedents to reach new frontiers.'"
    (quoting Porter v. Nutter, 
    913 F.2d 37
    , 41 (1st Cir. 1990))).
    - 27 -
    SELYA, Circuit Judge (concurring in the judgment).           I
    agree that the entry of a preliminary injunction enforcing the
    covenant not to compete should be affirmed.             In view of the
    district court's thorough and fully supportable findings of fact,
    CVS is likely to succeed in establishing that the covenant is
    enforceable.    Barring Lavin from assuming his role at PillPack for
    the   contractually    specified     eighteen-month     period   is   an
    appropriate means of protecting CVS's confidential information.       I
    part ways with the lead opinion, though, when it declines to choose
    between the two analytic frameworks that may potentially undergird
    this outcome.    See ante at 18, 25-26.        In particular, the lead
    opinion acknowledges two theoretical approaches for determining
    the reasonableness of a covenant.        See ante at 13-17.   Under what
    the lead opinion terms the "facial approach," a court must consider
    whether the full scope of the noncompetition bar is reasonable.
    By contrast, under what the lead opinion terms the "as-applied
    approach," a court must ask only whether it is reasonable to bar
    the employee from the specific form of competition in which he
    plans to engage.    In my judgment, the Rhode Island Supreme Court
    would adopt the facial approach.           The as-applied approach is
    inconsistent with the Rhode Island Supreme Court's description of
    the   reasonableness     test,     the    concerns    about   oppressive
    restrictions that motivate much of the law in this area, and the
    contours of the partial enforcement doctrine.
    - 28 -
    There are at least two persuasive reasons for concluding
    that the Rhode Island Supreme Court would adopt the facial approach
    (both of which are acknowledged by the lead opinion, see ante at
    14-15).      First,      that    court        has    repeatedly     stated    that    the
    reasonableness inquiry concerns the contract or agreement as a
    whole.    See, e.g., Cranston Print Works Co. v. Pothier, 
    848 A.2d 213
    , 219 (R.I. 2004); Durapin, Inc. v. Am. Prods., Inc., 
    559 A.2d 1051
    , 1053 (R.I. 1989); Oakdale Mfg. Co. v. Garst, 
    28 A. 973
    , 974
    (R.I.    1894).      Second,      the    court's       concerns     about    oppressive
    restraints    on    trade   align       much        more   neatly   with    the   facial
    approach.    Under Rhode Island law, "covenants not to compete are
    disfavored and subject to strict judicial scrutiny."                          Cranston
    
    Print, 848 A.2d at 219
    ; see 
    Durapin, 559 A.2d at 1053
    .                       This level
    of scrutiny protects employees from covenants that unreasonably
    limit their ability to seek employment or engage in trade.                           See
    
    Durapin, 559 A.2d at 1057-58
    ; Max Garelick, Inc. v. Leonardo, 
    250 A.2d 354
    , 357 (R.I. 1969).              Such considerations militate against
    conducting the reasonableness analysis in a manner that ignores
    the full scope of the terms of a covenant (as the as-applied
    approach would require us to do).
    In     all   events,        the     facial      approach   coheres       more
    logically with the doctrine of partial enforcement than does the
    as-applied approach.            Under the partial enforcement doctrine, a
    Rhode Island court may narrow the scope of an unreasonable covenant
    - 29 -
    and enforce it to whatever extent is reasonably necessary to
    protect the employer's legitimate interests.                         See 
    Durapin, 559 A.2d at 1058
    .       This analysis stands separate and apart from the
    facial approach, which examines the reasonableness of a covenant
    according to the full scope of its terms.                   It is only if the court
    finds   those     terms    unreasonable       that     the     partial    enforcement
    doctrine comes into play and permits the court to determine what
    restrictions       on     competition         are      reasonable         under      the
    circumstances.      See 
    id. The lead
    opinion's attempt to reconcile
    the partial enforcement doctrine with the as-applied approach is
    like trying to insert a square peg into a round hole.
    To be sure, in a case like the one before us — in which
    a former employee has defected to a direct competitor — the partial
    enforcement doctrine and the as-applied approach reduce to exactly
    the same question:          does the reasonable scope of the covenant
    encompass the employee's new position?                      To me, this redundancy
    plainly indicates that the threshold reasonableness inquiry must
    involve a broader question about the full scope of the covenant as
    written and counsels in favor of deploying the facial approach.
    To cinch the matter, there is an obvious lack of synergy
    between    the    as-applied       approach      to     reasonableness       and    the
    exceptions to partial enforcement for bad faith and deliberate
    overreaching      recognized       by   the    Rhode        Island    Supreme     Court.
    Although   a     Rhode    Island    court     may     not    partially    enforce     an
    - 30 -
    unreasonable covenant upon a finding of bad faith or deliberate
    overreaching on the employer's part, see 
    id., such a
    finding does
    not render a reasonable covenant unenforceable.                    Seen in this
    light, the as-applied approach effectively shifts the partial
    enforcement analysis into the threshold reasonableness inquiry
    while simultaneously eliminating an inquiring court's ability to
    consider an employer's bad faith or deliberate overreaching.                  This
    shift borders on the irrational; it would severely compromise the
    utility of these exceptions as a means of discouraging employers
    from deliberately foisting unreasonable and oppressive covenants
    on their employees.10        See Ferrofluidics Corp. v. Advanced Vacuum
    Components, Inc., 
    968 F.2d 1463
    , 1470-71 (1st Cir. 1992). I simply
    do   not   believe    that    the    Rhode     Island    Supreme    Court   would
    countenance such an odd dynamic.
    There    is   more.      The   harmful      effects    of   oppressive
    restrictions on competition — which discourage employees from
    seeking    other    employment      opportunities    due    to    the   threat   of
    litigation, see 
    id. at 1471
    — cannot plausibly be said to depend
    10
    Although the Rhode Island Supreme Court has never expressed
    this rationale for the exceptions to partial enforcement in so
    many words, its formulation of the doctrine derives from the
    Tennessee Supreme Court's decision in Central Adjustment Bureau,
    Inc. v. Ingram, 
    678 S.W.2d 28
    (Tenn. 1984). See 
    Durapin, 559 A.2d at 1058
    . In Ingram, the court focused on the risk of employers
    imposing oppressive restrictions on their employees when
    explaining why it would not partially enforce a contract that "is
    deliberately unreasonable and 
    oppressive." 678 S.W.2d at 37
    .
    - 31 -
    on how an employee may happen to violate his covenant.     Under the
    as-applied approach, though, that happenstance determines whether
    a court will find the covenant reasonable and, thus, whether the
    employee can point to an overly broad and oppressive covenant as
    evidence of bad faith or deliberate overreaching.    To this extent,
    the as-applied approach unduly restricts courts from using an
    employer's bad faith or deliberate overreaching as a tool to
    protect employees from oppressive covenants.    Once again, I cannot
    imagine that the Rhode Island Supreme Court would welcome such a
    result.
    With respect, I do not find convincing the lead opinion's
    suggestion that the as-applied approach might control here.      See
    ante at 15-17.      Although the Rhode Island Supreme Court has
    emphasized that the reasonableness inquiry must consider the facts
    and circumstances of each case, see, e.g., 
    Durapin, 559 A.2d at 1053
    ; Mento v. Lanni, 
    262 A.2d 839
    , 841-42 (R.I. 1970), this
    emphasis does not support, much less mandate, use of the as-applied
    approach.    It merely expresses the commonsense notion that the
    reasonableness of the restrictions contained in a covenant — such
    as temporal or geographic limitations — depends not on any bright-
    line rules but on the relationship of the parties and their
    particular interests.    See, e.g., Oakdale Mfg. 
    Co., 28 A.2d at 974
    ("[C]ontracts in restraint of trade are not necessarily void by
    reason of universality of time, nor of space; but they depend upon
    - 32 -
    the reasonableness of the restrictions under the conditions of
    each case."     (citations omitted)).      The Mento court considered
    facts about the parties in just this way, explaining that it was
    assessing     the   reasonableness   of    the   covenant's   "unlimited
    restriction as to 
    time." 262 A.2d at 842
    .      Contrary to the lead
    opinion's intimation, Mento simply does not suggest that a court
    can ignore the full scope of a covenant as written when determining
    its reasonableness.
    Similarly, the lead opinion's reliance on Professor
    Corbin's treatise does not get it very far.        The passage that the
    lead opinion cites appears in a section of the treatise entitled
    "Partial      Enforcement    of      Restrictive     Covenants"     and,
    unsurprisingly, discusses the partial enforcement doctrine, not
    the threshold reasonableness inquiry.        See ante at 16-17 (citing
    15 Corbin on Contracts § 80.26 (2019)).      The passage explains that
    a court deciding whether to partially enforce an unreasonable
    covenant need not always determine the boundaries of what would
    constitute a reasonable restriction.         See Corbin on Contracts,
    supra, § 80.26.      Instead, the operative question is "whether a
    restriction against what the [employee] has done in fact or is
    threatening to do would be a reasonable and valid restriction."
    
    Id. In short,
    what the lead opinion labels as part of the as-
    applied approach to the reasonableness inquiry is no such thing;
    - 33 -
    it   is   nothing   more   than   a    method   of   conducting   a   partial
    enforcement analysis.
    Nor do I find persuasive the lead opinion's suggestion
    that the facial approach is unworkable in the time-sensitive
    posture typical of lawsuits that seek to enforce covenants not to
    compete.    Refined to bare essence, the lead opinion's suggestion
    rests on the dubious proposition that the facial approach demands
    much more extensive discovery than the as-applied approach.              And
    to the extent that this proposition has any validity, it is
    undermined by the fact that preliminary injunctive relief normally
    does not require definitive resolution of underlying claims but,
    rather, requires only a prediction of whether the party seeking
    such relief is likely to succeed on the merits.            See Ross-Simons
    of Warwick, Inc. v. Baccarat, Inc., 
    102 F.3d 12
    , 16 (1st Cir.
    1996).
    With my prediction that the Rhode Island Supreme Court
    would take a facial approach to the reasonableness inquiry, the
    other pieces of the puzzle fall easily into place. The court below
    supportably found that Lavin failed to show that CVS engaged in
    either bad faith or deliberate overreaching when requiring him to
    sign the covenant.     See CVS Pharmacy, Inc. v. Lavin, 
    384 F. Supp. 3d
    227, 237 n.9 (D.R.I. 2019).           Accordingly, even if this court
    were to find the activity restriction in the covenant overly broad
    — a matter on which I take no view — I am confident that the Rhode
    - 34 -
    Island Supreme Court would partially enforce the covenant to the
    extent     reasonably    necessary    to     protect    CVS's      confidential
    information.    Whatever the terms of such a modified covenant would
    be, those terms would most assuredly encompass Lavin's new position
    at PillPack.
    There is one last hill to climb.           The lead opinion says
    that it is hesitant to take the approach that I have outlined
    because no Rhode Island court has used the doctrine of partial
    enforcement in precisely this manner.          See ante at 22-25.        In the
    circumstances of this case, I have no such hesitancy:                 the Rhode
    Island    Supreme   Court    has   straightforwardly        described   partial
    enforcement as allowing courts to "modify an unreasonable covenant
    and enforce it to an extent that it is reasonably necessary to
    protect the promisee's legitimate interests."               
    Durapin, 559 A.2d at 1058
    .    That is exactly what my proposed use of the doctrine of
    partial    enforcement      accomplishes.      Even    if    one    assumes   for
    argument's sake that the full activity restriction in the covenant
    is unreasonable, enforcing the covenant to bar Lavin from working
    at PillPack for an eighteen-month period would still be reasonably
    necessary to safeguard CVS's confidential information.
    This reasoning does not extend Rhode Island law merely
    because it makes assumptions to avoid thorny questions about the
    extent of the reasonable scope of Lavin's covenant.                Avoiding such
    unnecessary questions is a virtue of this approach, not a vice.
    - 35 -
    See United States v. Gertner, 
    65 F.3d 963
    , 973 (1st Cir. 1995)
    ("The judicial task, properly understood, should concentrate on
    those questions that must be decided in order to resolve a specific
    case."); see also Corbin on Contracts, supra, § 80.26 (approving
    this approach to conducting partial enforcement analysis).
    In sum, I would hold squarely that Rhode Island law takes
    the   facial   approach   for    determining   the   reasonableness   of   a
    covenant not to compete.        And I would affirm the district court's
    entry of a preliminary injunction on the basis of the partial
    enforcement doctrine.
    - 36 -