Gattineri v. Wynn MA, LLC ( 2023 )


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  •           United States Court of Appeals
    For the First Circuit
    No. 22-1117
    ANTHONY GATTINERI,
    Plaintiff, Appellant,
    v.
    WYNN MA, LLC; WYNN RESORTS LIMITED,
    Defendants, Appellees.
    APPEAL FROM THE UNITED STATES DISTRICT COURT
    FOR THE DISTRICT OF MASSACHUSETTS
    [Hon. F. Dennis Saylor, IV, U.S. District Judge]
    Before
    Barron, Chief Judge,
    Lynch and Gelpí, Circuit Judges.
    Stephen F. Gordon, with whom Todd B. Gordon, Robert A.
    DiSorbo, Kevin A. Robinson, and The Gordon Law Firm LLP were on
    brief, for appellant.
    Samuel M. Starr, with whom Caitlin A. Hill and Mintz, Levin,
    Cohn, Ferris, Glovsky & Popeo, P.C. were on brief, for appellees.
    March 22, 2023
    GELPÍ, Circuit Judge.        The appeal before us asks that we
    opine on a topic that raises important questions of Massachusetts
    state law and public policy: the regulation of gambling licenses
    in the Commonwealth.         The story begins with an option contract for
    the purchase of land for the construction of the Encore Boston
    Harbor resort and casino in Everett, Massachusetts (owned by
    Wynn MA, LLC, which, in turn, is wholly owned by Wynn Resorts,
    Limited).      The contract, between Encore and FBT Realty, LLC
    ("FBT"), of which Appellant Anthony Gattineri ("Gattineri") is a
    46.69% owner, gave Encore the option to purchase the land from FBT
    for    $75 million     should     the     Massachusetts       Gaming    Commission
    ("Commission") grant Encore a gaming license.             After some back and
    forth, the Commission ultimately conditioned the grant of the
    license on a $35 million purchase price for the sale of the land
    (a $40 million reduction from the original agreed-upon amount) and
    signed certification by each member of FBT that they were the sole
    owners of the company (after concerns were raised that someone
    with a criminal background also had an ownership interest in FBT).
    All    FBT   members    signed     the     required    certification,       except
    Gattineri, who for months refused to sign.             In June 2014, however,
    a   representative     for     Wynn MA,    LLC   and   Wynn    Resorts,    Limited
    (together, "Wynn Defendants") allegedly presented him an offer:
    Wynn   Defendants      would     "make    him    whole"   if    he     signed   the
    certification.       Gattineri ultimately accepted the offer (in an
    - 2 -
    alleged contract we term the "San Diego Agreement") and executed
    the   required     certification,    and   Wynn    Defendants     obtained     the
    license; but, according to Gattineri, he was never "made whole."
    Gattineri    consequently     sued    Wynn    Defendants    in   the
    U.S. District Court for the District of Massachusetts, alleging
    (1) breach    of   contract,    (2) common     law   fraud,     and   (3) unfair
    and/or deceptive trade practices in violation of state law.                   Wynn
    Defendants    sought     summary   judgment,      which   the   district   court
    granted on all counts, finding, among other things, no valid or
    enforceable contract.          Gattineri appeals, raising a number of
    alleged errors.      We reject flatly two arguments of error he makes.
    As to his claim of improper ex parte communication, he has failed
    to show any prejudice stemming from the communications between the
    district court’s clerk and the defendants.                As to his claim that
    the doctrine of in pari delicto defeats Wynn Defendants' arguments
    based on illegality, we reject the argument.              We do find that some
    of the alternative grounds on which the district court granted
    summary judgment to Wynn Defendants do not justify entry of summary
    judgment because they implicate genuine disputes as to material
    facts.   As to the core argument by Wynn Defendants (which affects
    all claims) that the San Diego Agreement is unenforceable as
    contrary to state law and/or as a violation of public policy, we
    conclude those questions are best certified to the Massachusetts
    Supreme Judicial Court ("SJC").
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    I. Background
    The civil appeal before us involves a dispute arising
    out of the sale of a tract of land in Everett and Boston (the
    "Parcel") for the construction of the Encore Boston Harbor. Before
    the resort and casino was built, the Parcel was owned by FBT, a
    limited liability company owned by Paul Lohnes, The DeNunzio
    Group, LLC    (owned   by   Dustin    DeNunzio,    Manager   of    FBT),   and
    Appellant Gattineri.
    We rehearse the facts, which are undisputed, unless
    otherwise noted, as the district court found them and in the light
    most favorable to the non-moving party, Gattineri.                Thompson v.
    Gold Medal Bakery, Inc., 
    989 F.3d 135
    , 138 (1st Cir. 2021).
    A. Facts
    1. Parties and Relevant Non-Parties
    We begin by outlining the players in this suit. Appellee
    Wynn MA, LLC is a Nevada limited liability company -- wholly owned
    by its sole member, Appellee Wynn Resorts, Limited -- with a
    principal place of business in Nevada.            Wynn Resorts, Limited is
    a publicly traded Nevada corporation also with a principal place
    of business in Nevada.      Wynn MA, LLC owns the Encore Boston Harbor.
    In January 2013, Encore filed for a Region A Category 1 gaming
    license to operate a resort in Massachusetts with the Commission,
    as required by state law.
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    Robert DeSalvio joined Wynn Resorts Development, LLC as
    Senior Vice President of Development in March 2014.1       He reported
    to Matthew Maddox, Chief Financial Officer, and Kim Sinatra, Senior
    Vice President and General Counsel, both at Wynn Resorts, Limited.
    2. FBT Membership Concerns
    During the licensing process, the Commission          became
    troubled by FBT's membership makeup at the time of the Option
    Agreement, discussed infra.      According to FBT, FBT was owned only
    by Gattineri, who held a 46.69% ownership interest; DeNunzio; and
    Lohnes.    However, the Commission expressed concerns that Charles
    Lightbody, a convicted felon and associate of La Cosa Nostra, might
    have had an ownership interest in FBT.
    The Investigations and Enforcement Bureau ("IEB") of the
    Commission,   which   conducts   suitability   investigations    of    all
    applicants for gaming licenses, conducted such an investigation of
    FBT and Wynn MA, LLC. On July 10, 2013, Massachusetts State Police
    officers   interviewed   Gattineri   about   his   membership,   and   on
    August 1, 2013, Kevin Tourek, Compliance Officer at Wynn Resorts,
    Limited, sent a letter to DeNunzio stating:
    Certain   regulatory    concerns   have   been
    expressed with respect to the ownership of
    [FBT]. On January 17, 2013, you advised Kim
    Sinatra in writing that the sole equity owners
    of FBT were yourself, Paul Lohnes and Anthony
    Gattineri. Can you please confirm any other
    1 DeSalvio became Encore's President in March 2018, years
    after the alleged San Diego Agreement took place.
    - 5 -
    direct or indirect equity participants since
    FBT took title to the property, indicating the
    period of ownership of each person? We would
    appreciate your response on or before August
    10, 2013.
    A few days later, DeNunzio replied:
    I write in response to your letter dated
    August 1, 2013. On October 9, 2009, [FBT] was
    organized by the filing of a Certificate of
    Organization with the Massachusetts Secretary
    of State. On October 15, 2009, FBT recorded
    the deed to the Everett property. The direct
    or indirect ownership of FBT since FBT took
    title is as follows:    The owners of FBT in
    2009 and 2010 were Paul Lohnes, Anthony
    Gattineri, Gary DeCicco and Charles Lightbody.
    In 2011, The DeNunzio Group, LLC became an
    additional owner of FBT. Dustin DeNunzio is
    the 100% owner of The DeNunzio Group, LLC.
    Gary DeCicco agreed to relinquish the extent
    of his ownership interest in FBT in early
    2012. Prior to the execution of the [O]ption
    [A]greement with Wynn on December 19, 2012,
    Charles Lightbody also agreed to transfer all
    of his ownership interest in FBT to Anthony
    Gattineri.   Since before December 19, 2012,
    and through the present, the sole equity
    owners (direct or indirect) of FBT have been
    Paul Lohnes, Anthony Gattineri and The
    DeNunzio Group, LLC.
    On September 5, 2013, Gattineri was served with a subpoena for
    testimony and records relating to the interest in FBT between him
    and Lightbody, and on October 15, 2013, Gattineri asserted his
    Fifth Amendment rights when the IEB attempted to interview him.
    Gattineri states that he obtained Lightbody's 12.05% membership
    interest in FBT via a Memorandum of Transfer and Promissory Note
    for $1.7 million.
    - 6 -
    On December 6, 2013, the IEB issued its Suitability
    Report, which set forth "the findings of fact relative to [the
    suitability] investigation" and included "concerns regarding the
    sellers of the property for the proposed casino site."
    3. The Parcel
    The    Parcel       at   issue    was   the    subject       of    an    Option
    Agreement signed by Encore, represented by Maddox, and FBT on
    December 19, 2012.          Through this agreement, Encore received the
    option to purchase the Parcel from FBT for $75 million.                             FBT was
    required to cooperate in the casino-licensing process:                               "Seller
    and   its   Affiliates          shall,   at   their   sole        cost   and        expense,
    reasonably     cooperate          with   Purchaser         with    respect          to   any
    information       it    reasonably       requires     to    complete          the    Casino
    Application and respond to any such inquiries throughout the
    licensing process."         "Affiliate" was defined as "any Person, any
    other   Person         which,     directly     or   indirectly,          Controls,       is
    Controlled by, or is under common Control with, such original
    Person."     The Option Agreement further provided:
    Seller represents and warrants to Purchaser
    that Seller and, to the best of Seller's
    knowledge, all Persons associated with Seller
    are willing to file all necessary applications
    to obtain whatever Approvals from the Gaming
    Regulatory Agencies may be required of such
    Persons in connection with this Agreement. To
    the best of Seller's knowledge, neither Seller
    nor any Person associated with Seller has ever
    engaged in any conduct or practices which any
    of the foregoing Persons should reasonably
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    believe would cause such Person to be denied
    any such Approvals.
    "Approvals" was defined as:
    [A]ll approvals, consents, licenses, permits,
    authorizations,       orders,       franchises,
    accreditations,     certificates,    variances,
    declarations,     concessions,    entitlements,
    waivers, exemptions waivers and similar items,
    including, without limitation, any license or
    approval    under    M.G.L.    Chapter 91,    a
    determination     under    the    Massachusetts
    Environmental Policy Act ("MEPA"), or an Army
    Corp of Engineer's Permit under the Federal
    Clean Water Act.
    Because the Parcel required environmental remediation at the time
    that   Encore   and   FBT   entered   into   the   agreement,   the   Option
    Agreement also required FBT to complete environmental cleanup
    activities, termed the "Seller's Environmental Obligations."             As
    outlined by the district court,
    the Option Agreement required[:] (1) Seller to
    diligently pursue, at the Seller's sole
    expense, a "Permanent Solution to any Releases
    of Oil and Hazardous Material at and From the
    Property" as soon as possible prior to
    closing; (2) Seller to reimburse Purchaser for
    reasonable out-of-pocket costs in the event of
    the Seller's breach; and (3) both parties to
    come to a mutually acceptable cost-sharing
    agreement related to the sharing of "any
    incremental costs" resulting from any releases
    of oil and hazardous material from the
    property.
    Gattineri v. Wynn MA, LLC, No. CV 18-11229-FDS, 
    2022 WL 123892
    , at
    *3 (D. Mass. Jan. 13, 2022).
    - 8 -
    However, on November 11, 2013, because, according to
    DeNunzio, the parties could not agree on a "mutually acceptable
    Environmental Cost-Sharing Agreement," DeNunzio emailed Jacqui
    Krum, Senior Vice President at Wynn             MA, LLC, announcing the
    "termination of the Option Agreement."           It should be noted that
    Gattineri     was     copied   on   several   emails    negotiating     the
    environmental       clean-up   obligations.      On   November 15,     2013,
    Gattineri informed his personal attorney, Daniel Doherty, that he
    "ha[d] no intention of cost sharing 30,000,000 [sic] for clean up
    because they want to disturb waterside . . . . Wynn and us are not
    anywhere near on the same page . . . ."
    4. The Ninth Amendment to the Option Agreement
    As      negotiations    regarding      FBT's    environmental
    remediation obligations continued, on November 21, 2013, Paul
    Feldman, FBT's attorney, emailed Wynn Defendants the following
    offer:   "Price is reduced to $31 million; Wynn takes over 100% of
    environmental and receives an assignment of the Pharmacia Judgment
    [a    court         judgment    concerning      environmental        cleanup
    responsibilities]."       Per DeNunzio, FBT and Wynn MA, LLC did not
    agree on FBT's environmental remediation obligations -- including
    how the Pharmacia Judgment would be allocated -- in the original
    Option Agreement and thus could not quantify the amount.
    As a result of these discussions, on November 26, 2013,
    Encore and FBT entered into a Ninth Amendment to the Option
    - 9 -
    Agreement providing that (1) both parties agreed "to amend the
    Agreement on the terms and conditions set forth below including,
    without limitation, to reduce the Purchase Price" to $35 million;
    (2) "[i]n all events [FBT's] monetary obligation for the Phase III
    Scope    of     Work    shall      not    exceed"   $10 million,    meaning    that
    $10 million of the purchase price would be set aside to pay for
    the     Seller's       environmental       obligations   and    certain   reports
    required      by    the      Massachusetts      Department     of   Environmental
    Protection; and (3) should FBT complete any of the work outlined
    in    another      section    of    the    agreement   prior   to   closing,   the
    $10 million should be reduced as such.               Gattineri did not sign the
    Ninth Agreement -- since he disagreed with the $40 million price
    reduction -- but could not prevent FBT from entering into the
    agreement.
    5. The Commission's Approval of the Ninth Amendment
    On December 5, 2013, Wynn MA, LLC submitted a petition
    to the Commission requesting review of their "proposed resolution
    to concerns raised by the [IEB] . . . about undisclosed interests
    in FBT," stating in part:
    5. Wynn commissioned an appraisal of the fair
    market value of the Property with the
    following assumptions: (i) that the Property
    would not be used for gaming purposes and
    (ii) that the environmental condition of the
    Property would be suitable for general
    commercial use.     Based on the foregoing
    assumptions, the appraisal valued the Property
    at [$35 million].
    - 10 -
    6. Wynn and FBT amended the Option Agreement
    to reduce the Purchase Price to [$35 million],
    the appraised value of the Property based upon
    the relevant assumptions.
    7. With respect to the required environmental
    remediation,   Wynn   and   FBT   agree   that
    environmental remediation necessary to bring
    the Property into regulatory compliance and
    make the Property suitable for general
    commercial    purposes     is    approximately
    [$10 million].    Therefore, pursuant to the
    terms of the revised Option Agreement, if Wynn
    exercises the option, Wynn will deposit [$10
    million] of the Purchase Price into an escrow
    account to be used for Phase III environmental
    remediation.   To the extent that the actual
    amount of the Phase III remediation is less
    than [$10 million], any remaining amounts will
    be paid to FBT.
    Consequently, the Commission held a public hearing to consider the
    proposal and approved the new $35 million purchase price:
    COMMISSIONER MCHUGH: All right. So then, I
    move   that  the   [C]ommission   accept   the
    resolution proposed by Wynn Mass to the issues
    that arose out of the land transaction about
    which we've heard today, with the essential
    ingredients that were outlined.
    That is that the sale price be 35 -- no more
    [than] $35 million with the $10 million
    proviso for cleanup cost, net -- net of the
    $10 million or whatever portion of that needs
    to be spent on -- on cleanup costs, number
    one.
    Number two, that the three members of FBT,
    LLC, who are nominally going to receive the
    proceeds be required to sign a document saying
    that they are the exclusive recipients of the
    proceeds, and that they do that on a notarized
    document under oath.
    - 11 -
    Moreover, the Commission directed the IEB "to deliver its entire
    file . . . to the U.S. attorney, the district attorney for Suffolk
    County, and the attorney general."          Gattineri learned of the
    Commission's decision, including the condition that all three FBT
    members sign a document under oath (the "Certificate") confirming
    that they would be the exclusive recipients of the proceeds, on
    December 13, 2016, from his personal attorneys, Jeffrey Doherty
    and   Bradford   Bailey.   While   Lohnes   and   DeNunzio   signed   the
    Certificate on December 23, 2013, stating the following, Gattineri
    refused to do so:
    The undersigned, being duly sworn, state and
    reaffirm, that to the best of their knowledge,
    the Representations of Seller set forth in
    Section 5 of the Ninth Amendment to Option
    Agreement dated November 26, 2013, by and
    between   FBT    Everett    Realty,   LLC,   a
    Massachusetts   limited    liability   company
    ("Seller") and Wynn MA, LLC, a Nevada limited
    liability company ("Purchaser") as follows:
    5. Representations of Seller.       To induce
    Purchaser to execute, deliver and perform its
    obligations under the Agreement, Seller hereby
    represents the following on and as of the
    Amendment Effective Date and on and as of the
    Closing Date:
    Schedule 3 [listing Lohnes, Gattineri, and The
    DeNunzio Group, LLC] is a true and accurate
    list of (i) each person with a legal or
    beneficial ownership interest direct or
    indirect,   in   Seller   (a   "Beneficiary"),
    (ii) the percentage interest in Seller of each
    such Beneficiary, and (iii) the address of
    each Beneficiary.     Neither Seller nor any
    Beneficiary has made, or has any agreement
    whether oral or written to make any payments
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    to any other person or entity from the
    proceeds of the Agreement including, without
    limitation, any of the option payments made
    pursuant to Section 2.2 or any portion of the
    Purchase Price.
    6. Ongoing Negotiations with Gattineri
    Gattineri remained steadfast in his refusal to sign the
    Certificate unless he was compensated, which became an issue for
    Wynn Defendants, who required his signature to obtain the gaming
    license.
    On January 24, 2014, Feldman, FBT's counsel, forwarded
    an email from Doherty, Gattineri's personal counsel, to Wynn
    representatives, outlining Gattineri's interests:
    I have talked with Anthony. He still wants to
    be bought out permanently at his share of
    $75,000,000.   The cram down to FMV has him
    entrenched. He thinks FBT has been played. I
    can't disagree with him. If the GC wants his
    signature, then the deal goes back to
    $75,000,000.   They can't have it both ways.
    Whether you agree with him or not, doesn't
    matter. That is what he wants.
    Among the recipients was Steve Tocco, one of Wynn Defendants'
    outside consultants.
    According to Gattineri, from March 2014 to June 2014,
    Wynn Defendants, primarily via DeSalvio, their representative,
    engaged him in a series of negotiations to obtain his signature.
    On April 14, 2014, he met with DeSalvio and Tocco for the first
    time. DeSalvio informed him that he had been tasked with obtaining
    his signature.   On April 15, 2014, he spoke to DeSalvio over the
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    phone to discuss his share of the $40 million price reduction.                 On
    April 18, 2014, Gattineri, DeSalvio, Tocco, and Doherty again met
    and    discussed   the   Certificate       and   Gattineri's    share   of   the
    $40 million price reduction.           A month later, on May 17, 2014,
    Gattineri spoke to DeSalvio over the phone about the Certificate.
    A few weeks later, on June 6, 2014, Gattineri again met with
    DeSalvio,     Tocco,   and   Doherty      to   discuss   the   Certificate   and
    Gattineri's share of the $40 million price reduction.                Gattineri
    again refused to sign unless he was paid his percentage of the
    price reduction.
    7. The Alleged San Diego Agreement
    Finally, on June 14, 2014, Gattineri met with DeSalvio
    at    the   Westgate   Hotel   in   San    Diego,   California,    where     they
    allegedly verbally agreed to the San Diego Agreement.                Gattineri
    contends that after DeSalvio represented that he had authority to
    enter into an agreement with him, they agreed to the following:
    "If Anthony Gattineri signed the required [C]ertificate and Wynn
    obtained the casino license for a casino on the FBT property, Wynn
    would 'make Anthony Gattineri whole.'"            Per Gattineri, "making him
    whole" would involve Wynn paying him approximately $19 million:
    Q. Did you and Mr. DeSalvio talk about a
    particular amount?
    A. I think I said it was around $19 million or
    19 million. I didn't know the exact dollar.
    Q. How did you make the calculation?
    - 14 -
    A. Well, I took the $75 million, and I
    multiplied it, obviously, by around 48
    percent, and I came up with around 18 and a
    half, $19 million.
    Q. Did you have a specific amount that you and
    Mr. DeSalvio had discussed?
    A. Not to the penny.
    Q. To the dollar?
    A. I think what I said,        it   was   around
    $19 million or that comment.
    According to Gattineri, the $19 million calculation was his 46.69%
    portion of the $40 million reduction -- $18,676,000 -- not taking
    into account FBT's   environmental-cleanup obligation under the
    original Option Agreement:
    Q. And -- and how were you going to calculate
    what that means to make you whole? What --
    what were you going to do?
    A. I would probably just do some simple math
    and have someone with a better math background
    than I am, I'm not very good with math. And
    calculate   the,   whatever,   the   46.7   at
    $75 million and that's what I'm owed. That's
    what I need to make me whole.
    Q. What adjustment would you make for the
    seller's obligation under the original option
    agreement to perform environmental work?
    A. I wouldn't be doing any of that. I think
    -- I think Wynn -- I think Wynn knew the
    environmental issue. I don't really know what
    they were doing with Monsanto and the
    agreements they were making. I have no idea.
    - 15 -
    Q. You have no idea what obligations FBT
    assumed under the original option agreement
    for seller's environmental clean up?
    A. I don't recall if, if we were responsible
    for any of it or it was -- it seemed like it.
    I have no idea how much the money was.
    Gattineri further specified that this was not the only way to make
    him "whole," rather:
    Q. That was one of the ways to make you whole
    would be that Wynn possibly would buy real
    estate that you had an interest in?
    A. Yeah, they have a real estate division
    under some development company that they could
    do it that way.
    Q. So they could buy the property?
    A. I don't know how they do.   They know how to
    do it they said.
    Q. Is that one of the things that you and Mr.
    DeSalvio talked about, the possibility that
    after you got cleared of the investigation
    that if you had other real estate in the
    greater Boston area perhaps Wynn could become
    a purchaser of that real estate; is that
    something you guys talked about in San Diego?
    A. We talked about it at different times. If
    I was cleared and found 100[%] exonerated and
    not guilty, you could definitely get something
    done.
    Q. And one of the ways to get something done
    might have been that Wynn could buy some
    property that you had for sale in the area?
    A. Very possibly be that. That would be up to
    them. They have all kinds of ways to do it.
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    On June 14, 2014, a few hours after his meeting with DeSalvio,
    Gattineri signed the Certificate.            Four days later, Doherty sent
    the Commission a copy of the Certificate.               In September 2014, the
    Commission granted Encore the gaming license, leading to the
    purchase of the Parcel for $35 million.            Gattineri did not receive
    the $19 million that he claims he is owed.
    8. Gattineri's Indictments
    On October 1, 2014, Gattineri, DeNunzio, and Lightbody
    were indicted in the U.S. District Court for the District of
    Massachusetts for wire fraud and conspiracy to commit wire fraud;
    more specifically, for conspiring to defraud Wynn Defendants and
    the Commission by covering up Lightbody's financial interest in
    the Parcel.     Id. at *8.     A couple of weeks later, Gattineri was
    indicted   in   Massachusetts      state   court    for    impeding     a   gaming
    investigation,    conspiracy,      and   tampering       with   evidence.      Id.
    However,   Gattineri    was    acquitted     of    all    federal    charges   on
    April 29, 2016, following a jury trial, and his state-court case
    ended    when   the    prosecution       entered    a     nolle     prosequi   on
    September 29, 2016.      Id.
    9. The Chapter 93A Demand Letter
    In April 2018, Wynn Defendants received a demand letter
    from    Gattineri's    attorneys    alleging       that    they   had   violated
    Massachusetts General Laws Chapter 93A by engaging in "unfair
    - 17 -
    and/or deceptive trade practices" and had breached the following
    contract with Gattineri:
    [O]n June 14, 2014 . . . Wynn, through its
    duly    authorized   representative    Robert
    DeSalvio, offered Anthony Gattineri to "make
    him whole" on Anthony Gattineri's loss of
    $18,676,000 (46.69% of $40 million) if
    (a)    Anthony   Gattineri    signed    a
    Certificate that Wynn needed to present to the
    Massachusetts    Gaming   Commission . . . in
    order for Wynn to obtain a casino license for
    the FBT property in Everett . . . upon which
    Wynn had an Option to Purchase; and
    (b) So long as Anthony Gattineri had
    committed no crime in connection with the sale
    of the FBT Property to Wynn.
    In June 2018, Gattineri filed this suit against Wynn Defendants
    alleging     (1) breach    of   contract;     (2) common   law    fraud;     and
    (3) unfair    and/or    deceptive     trade   practices    in    violation   of
    Chapter 93A, section 11 of the Massachusetts General Laws, arguing
    that Wynn Defendants "fail[ed] to make him whole" because they did
    not pay him "his 46.69% share of the $40 million price reduction
    windfall that [they] received" and seeking nearly $19 million in
    damages.
    10.     The     District   Court's    Communication      with    Wynn
    Defendants
    During the course of the suit, Wynn Defendants filed a
    motion for summary judgment.          In support thereof, they included
    (1) a memorandum of law, (2) a statement of undisputed material
    facts, and (3) a declaration containing forty exhibits.              Included
    - 18 -
    in these exhibits were Exhibit 16, containing excerpts of the
    December 12, 2019 deposition of Daniel Doherty, and Exhibit 38,
    containing       excerpts    of    the     October 23,    2020    deposition    of
    Gattineri.       The statement of undisputed material facts included a
    paragraph stating, "Mr. Gattineri did not agree to sign the
    Certificate during the breakfast meeting in San Diego, but a few
    hours after the San Diego Meeting, Mr. Gattineri notified Mr.
    DeSalvio that he would sign the Certificate."              The statement cited
    page 73    of    Volume II    of   Gattineri's       deposition    (Exhibit 38);
    however, that specific page was left out of Exhibit 38.                  About a
    month later, Gattineri filed an opposition to the motion for
    summary judgment, a statement of material facts in dispute, and
    thirty-three additional exhibits.                 While Gattineri's Exhibit 2
    contained counter-designated excerpts from Gattineri Volume II, he
    did not include page 73 from Gattineri Volume II as part of
    Exhibit 2, nor did he dispute               or object to     Wynn Defendant's
    citation to page 73 in his statement of material facts in dispute.
    As such, no party filed full transcripts of Gattineri Volume II.
    Shortly thereafter, Wynn Defendants filed their reply, and a
    hearing on the motion for summary judgment was held on December 23,
    2020.
    Although not reflected in the district court docket, a
    year    later,    the   district    court     courtroom   clerk    emailed     Wynn
    - 19 -
    Defendants' counsel, without including Gattineri's counsel, the
    following:
    The law clerk for the judge was wondering if
    they could have a copy of the entire
    deposition from exhibit 16 [Daniel Doherty's
    deposition] on D. 135. As well as Gattineri
    Vol II   transcript  which   I  believe   is
    Exhibit 38. You can email it to me by pdf if
    that works. Your help is much appreciated.
    Consequently, Wynn Defendants' counsel replied with the requested
    exhibits (Exhibit 16 and 38).    At this point, Gattineri's counsel
    was unaware of this communication.
    In January 2022, the district court granted summary
    judgment on all three counts in favor of Wynn Defendants.       The
    grant cited four pages of Gattineri Volume II (page 32, 73, 112,
    and 113), all of which were cited in Wynn Defendants' statement of
    undisputed material facts and were included in Exhibit 38, except
    page 73.     Id. at *7-8.   The text accompanying the citation to
    page 73 read:    "Gattineri did not agree to sign the Certificate
    during the meeting in San Diego.     However, a few hours after the
    meeting, he notified DeSalvio that he would sign the Certificate.
    (Gattineri Dep. Tr. II:73; Hill Dec. Ex. 5, DeSalvio Dep. Tr. 76)."
    Id. at *8.
    Thereafter, Gattineri filed this appeal.   While amassing
    the contents of the joint appendix for appeal, Gattineri's counsel
    learned of the email string between the courtroom clerk and Wynn
    - 20 -
    Defendants' counsel and that the full transcripts of the two
    depositions had been provided to the district court.
    B. Procedural History
    As aforementioned, the district court ultimately granted
    summary judgment in favor of Wynn Defendants and concluded that
    (1) the alleged San Diego Agreement constitutes an "unenforceable
    illegal     contract"      under     Chapter 23K     of   the   Massachusetts
    General Laws; (2) an essential term of the alleged San Diego
    Agreement -- the amount Gattineri would be paid in exchange for
    his signature -- was too indefinite and uncertain to form a valid
    contract; (3) Gattineri's supposed reliance on Wynn Defendants'
    representations was too unreasonable, foreclosing a claim for
    common law fraud; and (4) Gattineri's Chapter 93A claim was barred
    because it is "wholly derivative" of his breach-of-contract and
    common-law fraud claims.           Id. at *10, 13, 14.    This timely appeal
    followed.
    II. Discussion
    On   appeal,    Gattineri     requests   reversal   based   on   an
    alleged taint caused by the ex parte communication between the
    district court courtroom clerk and Wynn Defendants' counsel and
    contends that the district court erred in granting Wynn Defendants'
    motion for summary judgment.            We ultimately reject Gattineri's
    improper ex parte communication claim and in pari delicto argument,
    conclude that there are genuine disputes of material facts related
    - 21 -
    to his contract and fraud claims, and finally determine that
    whether Gattineri's claims can succeed hinges on whether the San
    Diego Agreement is unenforceable as contrary to state law and/or
    as a violation of public policy.           Because the enforceability of
    the agreement is dispositive of this case, we certify the questions
    outlined below to the SJC.
    A. Alleged Taint
    We begin with the claim regarding the alleged taint.
    Gattineri   contends    that    the    district   court      courtroom   clerk's
    communication    with    Wynn     Defendants'          counsel   violated    the
    prohibition on ex parte communications in Canon 3(A)(4) of the
    Code of Conduct for United States Judges and that the district
    court's citation to page 73 provides adequate proof to warrant
    reversal.    Wynn Defendants counter that reversal is not required
    because the communication was purely administrative and did not
    provide any procedural, substantive, or tactical advantage to Wynn
    Defendants, and because Gattineri has not pointed to any prejudice
    suffered. We agree with Wynn Defendants that Gattineri has utterly
    failed to show prejudice.
    Canon 3(A)(4) prohibits ex parte communications except
    for "scheduling, administrative, or emergency purposes" so long as
    the "communication does not address substantive matters and the
    judge reasonably believes that no party will gain a procedural,
    substantive,    or   tactical     advantage       as     a   result   of"   said
    - 22 -
    communication.     Code of Conduct for U.S. Judges, Canon 3(A)(4).
    While Gattineri argues that the communication runs afoul of the
    canon, it simply "makes no difference on . . . appeal whether the
    district court violated the pertinent canon unless that violation
    somehow could have tainted the judgment from which [Gattineri]
    appeals," Law Offs. of David Efron v. Matthews & Fullmer L. Firm,
    
    782 F.3d 46
    , 55 (1st Cir. 2015), and he has failed to make such a
    showing here.
    The information taken from these documents ("Gattineri
    did not agree to sign the Certificate during the meeting in San
    Diego.      However, a few hours after the meeting, he notified
    DeSalvio that he would sign the Certificate.") does not play a
    significant role in the arguments now before us and was previously
    included in Wynn Defendants' statement of undisputed facts, which
    Gattineri    at   no   point    challenged.        See   L.R.,    D. Mass.   56.1
    ("Material facts of record set forth in the statement required to
    be served by the moving party will be deemed for purposes of the
    motion to be admitted by opposing parties unless controverted by
    the   statement   required      to   be   served   by    opposing   parties.");
    Schiffmann v. United States, 
    811 F.3d 519
    , 525 (1st Cir. 2016)
    (noting non-movant's failure to challenge fact means fact is
    "deemed   admitted").          Neither    party    disputes      that   Gattineri
    originally refused to sign the Certificate, nor that he later
    agreed to do so.       Even if we were to consider the full transcript
    - 23 -
    of both depositions substantively, Gattineri leaves us to guess as
    to how they might have provided a "procedural, substantive, or
    tactical   advantage"   to    Wynn    Defendants,    especially   where    the
    district court cited only to a single page.           See, e.g., Law Offs.
    of David Efron, 
    782 F.3d at 55
     (rejecting a claim of prejudice
    where the appellant "point[ed] to no . . . plausible [taint due to
    an ex parte communication], and instead merely assert[ed] in a
    conclusory form that such a supposed violation infringed on his
    due process rights").       We refuse to do such guesswork.
    Gattineri also argues that the district court must have
    conducted and been influenced by an "apparently negative[] review"
    of the emailed material because, in denying a motion by Wynn
    Defendants    to   strike    portions   of    an   affidavit   submitted   by
    Gattineri during summary judgment briefing, the court "expressed
    a 'serious question concerning [Mr.] Gattineri's credibility.'"
    (Alteration in original.) This argument takes the district court's
    statement out of context.            Wynn Defendants' motion to strike
    invoked the "sham affidavit rule," seeking to strike portions of
    Gattineri's    affidavit      that    were    allegedly   contradicted     by
    statements Gattineri had made in his deposition.                  See, e.g.,
    Escribano-Reyes v. Pro. HEPA Certificate Corp., 
    817 F.3d 380
    , 386
    (1st Cir. 2016) (explaining "sham affidavit rule" prohibits a party
    from creating conflict and resisting summary judgment with an
    affidavit that contradicts its unambiguous responses to questions
    - 24 -
    asked during discovery).          The "credibility" language Gattineri
    quotes in his brief appeared in the district court's discussion of
    a specific "discrepancy" between Gattineri's deposition testimony
    and his summary judgment affidavit that, the court concluded,
    "raise[d] a serious question concerning Gattineri's credibility"
    but did not warrant striking the relevant part of the affidavit.
    The court did not express a generalized concern about Gattineri's
    credibility    or    reference    the   deposition   materials    introduced
    through the ex parte communication.             Nothing in the district
    court's reasoning suggests that those materials played any role in
    its decision on the motion, which was favorable to Gattineri.
    Because Gattineri has failed to show prejudice, his
    claim fails.
    B. Breach of Contract
    Having     rejected     Gattineri's      improper     ex   parte
    communication claim, we next turn to Gattineri's breach of contract
    argument.
    "We review a district court's grant of summary judgment
    de novo."     Triangle Cayman Asset Co. v. LG & AC, Corp., 
    52 F.4th 24
    , 32 (1st Cir. 2022).      Summary judgment "is appropriate only if
    'there is no genuine dispute as to any material fact and the movant
    is entitled to judgment as a matter of law.'"                   
    Id.
     (quoting
    Fed. R. Civ. P. 56(a)).          A genuine dispute is one that "would
    permit a rational factfinder to resolve the issue in favor of
    - 25 -
    either party," and a material fact is one that has the "potential
    to affect the outcome of the suit under the applicable law."
    Joseph v. Lincare, Inc., 
    989 F.3d 147
    , 157 (1st Cir. 2021) (first
    quoting Medina-Munoz v. R.J. Reynolds Tobacco Co., 
    896 F.2d 5
    , 8
    (1st Cir. 1990); and then quoting Cherkaoui v. City of Quincy, 
    877 F.3d 14
    , 23 (1st Cir. 2017)).             We further "draw[] all reasonable
    inferences in favor of the non-moving party," here, Gattineri.
    Doe v. Trs. of Bos. Coll., 
    892 F.3d 67
    , 79 (1st Cir. 2018) (quoting
    Roman Cath. Bishop of Springfield v. City of Springfield, 
    724 F.3d 78
    , 89 (1st Cir. 2013)).
    In     federal    diversity    cases,   state      law   supplies    the
    substantive      rules   of    decision,     and    the   parties     agree     that
    Massachusetts law controls.         Erie R.R. Co. v. Tompkins, 
    304 U.S. 64
    , 78 (1938); see also Cochran v. Quest Software, Inc., 
    328 F.3d 1
    , 6 (1st Cir. 2003) ("It is settled in this circuit that when the
    parties have reached a plausible agreement about what law governs,
    a federal court sitting in diversity jurisdiction is free to forgo
    independent inquiry and accept that agreement.").
    In     granting     summary     judgment      in    favor     of    Wynn
    Defendants, the district court found that the alleged San Diego
    Agreement     is    unenforceable     because       (1) it      is   an   "illegal
    contract," and, "even if it were not," (2) "the terms are not
    sufficiently definite or certain to form the basis of a valid
    contract."    Gattineri, 
    2022 WL 123892
    , at *10.               As to the legality
    - 26 -
    of the contract, it is unclear as a matter of law whether the
    contract is indeed illegal because that matter rests on unresolved
    issues of Massachusetts law.            Since we cannot determine whether
    the contract is enforceable, we certify these issues to the SJC.
    See infra II.F.        As to the validity of the contract, we agree with
    Gattineri that one of the grounds on which the district court
    relied in granting summary judgment -- Wynn Defendants' argument
    that the contract was not sufficiently definite or certain -- was
    legally insufficient because there are material facts in genuine
    dispute.
    To put forth a viable breach of contract claim under
    Massachusetts law, Gattineri "must prove that a valid, binding
    contract existed, the defendant breached the terms of the contract,
    and [he] sustained damages as a result of the breach."             Brooks v.
    AIG SunAmerica Life Assurance Co., 
    480 F.3d 579
    , 586 (1st Cir.
    2007).     A valid contract exists where all the essential terms are
    "definite and certain so that the intention of the parties may be
    discovered,      the     nature   and     extent   of   their    obligations
    ascertained, and their rights determined."              Cygan v. Megathlin,
    
    96 N.E.2d 702
    , 703 (Mass. 1951) (emphasis added).
    At   the    summary   judgment   stage   and   on   appeal,   Wynn
    Defendants dispute whether a valid contract existed, arguing that
    they are entitled to summary judgment on the contract claim because
    "a material term in the alleged San Diego Agreement -- the amount
    - 27 -
    that    would     make     [Gattineri]       'whole' -- is        indefinite       and
    uncertain."       Gattineri counters that prior to the San Diego
    Agreement, Wynn Defendants were well aware that the amount that
    would "make him whole" was his percentage (46.69%) of the price
    reduction ($40,000,000), in essence, $18,676,000.                        The district
    court disagreed with Gattineri, finding the alleged agreement
    vague since "there is no evidence that [Gattineri] and DeSalvio
    even   discussed"      what    it    would   mean   to    "make    him    whole"   and
    "Gattineri . . . testified that he did not know how the price would
    be    adjusted    to   take      into   account     the    environmental-cleanup
    obligation that FBT had under the original Option Agreement."
    Gattineri, 
    2022 WL 123892
    , at *12.                On appeal, Gattineri claims
    that the record does not support such a finding.                          Viewing the
    record in the light most favorable to Gattineri, as we do at the
    summary judgment stage, we conclude that Gattineri has enough
    evidence to persuade a reasonable jury that "making him whole" had
    a    definite    meaning      because    (1) the    only    material       term,   the
    approximately $18,676,000 that would make Gattineri "whole," was
    definite and certain and (2) the parties negotiated with the
    understanding     that     the      environmental   cleanup       costs    would   not
    factor into this calculation.
    First,     the     record    contains    evidence      via     affidavit,
    deposition, and email tethering "making Gattineri whole" to his
    percentage of the price reduction such that a reasonable factfinder
    - 28 -
    could    conclude     that    "making       Gattineri       whole"    had   a    definite
    meaning.     For instance, in Gattineri's affidavit -- accompanying
    his opposition to Wynn Defendants' summary judgment motion -- he
    states    that   in    the    months       preceding     the    alleged      San    Diego
    Agreement, he met with DeSalvio multiple times and expressed his
    "desire to be made whole on [his] percentage of the $40 [m]illion
    price reduction."       (Emphasis added.)            On April 15, 2014, "DeSalvio
    called [Gattineri] to discuss the Certificate and [his] share of
    the $40 million price reduction."                   (Emphasis added.)       Three days
    later,     another    meeting        was     held    where     Gattineri        "made   it
    clear . . . that [he] would not sign anything unless [he] was made
    whole on [his] percentage of the price reduction."                              (Emphasis
    added.)     About a month later, Gattineri and DeSalvio again spoke
    about the Certificate.         A few weeks later, Gattineri again refused
    to sign the Certificate "unless [he] was made whole on [his]
    percentage of the $40 [m]illion price reduction."                               (Emphasis
    added.)     Further, Wynn Defendants were aware of this percentage
    since FBT's counsel forwarded to Wynn representatives an email
    from Gattineri's personal counsel to FBT's counsel stating that
    Gattineri "still wants to be bought out permanently at his share
    of   $75,000,000."           While    DeSalvio,       who    had     been   in    alleged
    negotiations with Gattineri, was not copied on this email, Tocco,
    who had accompanied DeSalvio to meetings with Gattineri on at least
    three occasions, was copied.               This supports a reasonable inference
    - 29 -
    that DeSalvio knew the amount that would "make Gattineri whole"
    either because the parties discussed that figure at the meetings
    that Tocco attended or because Tocco knew and told DeSalvio.
    While Wynn Defendants would have us believe that the
    alleged San Diego Agreement was reached in a vacuum and hence that
    the amount that would "make Gattineri whole" was not certain,
    taking the evidence in the light most favorable to Gattineri, the
    series of conversations that led to Gattineri's signature suggest
    otherwise.      See Simons v. Am. Dry Ginger Ale Co., 
    140 N.E.2d 649
    ,
    652 (Mass. 1957) (finding essential terms sufficiently definite in
    part because "[t]he parties had been engaged in dealings with each
    other over a considerable period of time"). Given Wynn Defendants'
    dire need    to secure Gattineri's signature and the number of
    conversations that led up to the alleged San Diego Agreement, a
    reasonable factfinder could conclude that the parties were clear
    on what it would take to "make Gattineri whole."
    Wynn Defendants contend that the amount was undefined
    because when Gattineri was asked, in his deposition, whether he
    and DeSalvio had discussed a "specific" amount that he would need
    in   exchange    for   his   signature,   he   stated   that   they   had   not
    discussed a figure "to the penny."             But Gattineri also provided
    evidence in his deposition that he and DeSalvio had discussed the
    amount necessary to "make him whole" in terms of the percentage of
    the price reduction -- a concrete, readily calculable figure --
    - 30 -
    and calculated that amount to be "around $19 million."             See 
    id.
    ("[A] contract is not to be held unenforceable 'if, when applied
    to the transaction and construed in the light of the attending
    circumstances,' the meaning can be ascertained with reasonable
    certainty.").   Moreover, Wynn Defendants were in receipt of the
    email from Gattineri's personal counsel specifying that he sought
    "his share of $75,000,000."       Taken together, these pieces of
    evidence could lead a reasonable factfinder to conclude that
    "making Gattineri whole" had a definite meaning.
    Second, Wynn Defendants argue that the alleged San Diego
    Agreement is also "indefinite and uncertain" because a second
    material term was unknown: "the cost of FBT's environmental cleanup
    obligations, a cost which would have reduced the amount that FBT
    would have received under the original Option Agreement and was,
    according to FBT's Manager, never quantified."            But even if the
    term was unknown, the record reveals that Gattineri and DeSalvio
    did not consider this cost in negotiating the amount needed to
    "make him whole."   As Gattineri argues, they could not have since
    DeSalvio was unaware of these obligations.            According to his
    deposition, DeSalvio had never seen the Option Agreement, much
    less read it, and only learned of the Certificate requirement and
    the $40 million reduction "[f]rom a meeting with Kim Sinatra."            If
    DeSalvio was unaware of the Option Agreement's contents, and thus
    FBT's   environmental   obligations,   he   could   not    have   had   this
    - 31 -
    quantity in mind during his many negotiations with Gattineri. Wynn
    Defendants do not dispute this argument.          As such, a reasonable
    factfinder could conclude that the parties mutually understood the
    San Diego Agreement's only material term to be the amount needed
    to "make Gattineri whole" and as already explained, a reasonable
    factfinder    could   conclude   that   that   amount   was   sufficiently
    definite and certain to survive summary judgment.
    Wynn Defendants aptly point out that Gattineri testified
    that there may have been other ways to "make him whole," such as
    buying real estate in which he had an interest.               It therefore
    follows, they argue, that the amount it would take to "make him
    whole" must be uncertain and indefinite.        But this is not the only
    conclusion.    Rather, a reasonable factfinder could conclude that
    the amount in real estate that Wynn Defendants would need to
    purchase to "make him whole" should equal his percentage of the
    price reduction.       In other words, the amount is certain and
    definite -- $18,676,000 -- but the method of payment is flexible.
    Thus, because there are genuine issues of material fact
    in dispute, we part ways with the district court's reasoning.
    Summary judgment may ultimately be appropriate, but we are unable
    to answer this question until we hear from the SJC on the certified
    questions we pose.
    - 32 -
    C. Common Law Fraud
    The district court also granted summary judgment for
    Wynn Defendants on Gattineri's common law fraud claim.         Like
    Gattineri's breach of contract claim, we review the decision de
    novo, drawing all reasonable inferences in favor of the non-moving
    party, Gattineri,    Trs. of Bos. Coll., 
    892 F.3d at 79
    , and because
    we are sitting in diversity, state law applies, Cochran, 
    328 F.3d at 6
    .
    To prove a claim for common law fraud under Massachusetts
    law, a party must "show[] that (1) the defendant made a 'false
    representation of a material fact with knowledge of its falsity
    for the purpose of inducing [the plaintiff] to act thereon';
    (2) the plaintiff 'relied upon the representation as true and acted
    upon it to his [or her] detriment'; and (3) such 'reliance was
    reasonable under the circumstances.'" H1 Lincoln, Inc. v. S. Wash.
    St., LLC, 
    179 N.E.3d 545
    , 560 (Mass. 2022) (alterations in the
    original) (quoting Rodi v. S. New Eng. Sch. of L., 
    532 F.3d 11
    , 15
    (1st Cir. 2008)).      Further, "the reasonableness of a party's
    reliance is ordinarily a question of fact for the jury."      Rodi,
    
    532 F.3d at 15
    .     However, it "can be a question of law where the
    undisputed facts permit only one conclusion" such that "no rational
    jury could [find] reasonable reliance."   Cumis Ins. Soc'y, Inc. v.
    BJ's Wholesale Club, Inc., 
    918 N.E.2d 36
    , 50 (Mass. 2009).
    - 33 -
    The district court found, as a matter of law, that
    Gattineri could not have reasonably relied on Wynn Defendants'
    representations because an essential term of the agreement -- what
    would "make Gattineri whole" -- was "imprecise," "undecided," and
    "entirely unclear."              Gattineri, 
    2022 WL 123892
    , at *13.               We
    disagree.
    As discussed supra, the record contains evidence tying
    what would "make Gattineri whole" to his percentage of the price
    reduction, such that a reasonable factfinder could conclude that
    what     would     "make      Gattineri     whole"    would    be   approximately
    $18,676,000.       The fact that DeSalvio represented Wynn Defendants
    in     the    negotiations       with     Gattineri     and   was   unaware     that
    environmental cleanup costs could be factored into the final
    purchase price belies the district court's finding that the amount
    owed    to    Gattineri,       $18,676,000,    was    imprecise,    undecided,    or
    entirely unclear.            This is especially the case since a factfinder
    may     consider       the    context     surrounding     a   representation     in
    determining whether a party's reliance was reasonable.                   See McEvoy
    Travel Bureau, Inc. v. Norton Co., 
    563 N.E.2d 188
    , 194 (Mass. 1990)
    (finding party's reliance reasonable in part given "long existing
    relationship between the parties").              Gattineri did not request to
    be "made whole" once and in a vacuum.                    Instead, he repeatedly
    linked       "making   him     whole"   with   the    percentage    of   the   price
    reduction in the various meetings he had with DeSalvio leading up
    - 34 -
    to the alleged San Diego Agreement.             We simply cannot ignore this
    context.
    The   district    court      failed      to    take   context     into
    consideration and instead incorrectly relied on Masingill v. EMC
    Corp., 
    870 N.E.2d 81
    , 91 (Mass. 2007).                But Masingill is readily
    distinguishable.        First,    the     alleged      promise     in   that   case
    contradicted the terms of a written contract.               See id. at 91.      Wynn
    Defendants have not argued that that is the case here.                       Second,
    the surrounding circumstances make the alleged promise in this
    case more definite than the one in Masingill. There, the plaintiff
    alleged that a corporation's agent had misrepresented to her that
    she would be "made whole" if she left her then-employer to work
    for a different company.         See id. at 87, 91.         While the SJC found
    the statement "too vague to support the cause of action," it
    underscored that in reaching this conclusion it considered the
    evidence in its entirety, not just that statement alone.                     Id. at
    91   ("The   evidence   does     not    offer   any    definition       or   further
    explanation of the term 'make you whole' sufficiently precise to
    determine what the representation meant.").                The SJC further noted
    that when Masingill was asked at trial whether the company's agent
    had ever "told [her] what he meant" by "make you whole," Masingill
    responded, "[n]o." Id. at 91 n.24. Unlike in Masingill, Gattineri
    repeatedly tied his percentage of the $40 million price reduction
    with being "made whole" and even put forth the number $19 million.
    - 35 -
    As such, a reasonable factfinder could conclude that sufficient
    "definition or further explanation" existed to make Gattineri's
    reliance reasonable.
    Thus, because a reasonable factfinder could find that
    what would "make Gattineri whole" was sufficiently clear, the
    district court's entry of summary judgment for Wynn Defendants was
    not warranted. Again, summary judgment may ultimately be justified
    on this claim, but this conclusion turns on the SJC's response to
    the questions we certify below.
    D. Chapter 93A
    As we have explained above, we differ with the district
    court's conclusion that the material terms of the San Diego
    Agreement were not sufficiently definite and certain to form the
    basis of a valid contract.    Moreover, we certify the other grounds
    on which the district court determined that the San Diego Agreement
    is unenforceable.     See infra II.F.      The district court did not
    reject Gattineri's 93A claim on any ground that we reject at this
    stage; but because whether the alleged contract is unenforceable
    affects this claim, we await the SJC's answer to our questions
    before addressing it in full.
    E. In Pari Delicto
    Before discussing the legality of the alleged San Diego
    Agreement,   we   first   dispose   of   Gattineri's   in   pari   delicto
    argument. He contends that even if the alleged San Diego Agreement
    - 36 -
    is illegal, it should still be enforced because the parties are
    not in pari delicto, or at equal fault.                Instead, he argues that
    he is entitled to equitable relief because he was excusably
    ignorant of the fact that the San Diego Agreement was potentially
    violative     of    Massachusetts          law   and    "excusable      ignorance
    allows . . . courts to enforce a contract . . . where one party
    was more likely than the other to have knowledge that the contract
    in question was potentially violative of a statute."                         We are
    unpersuaded.
    The   in     pari   delicto    defense    is     limited   to   "those
    situations    in    which    (i)   the     plaintiff,       as   compared    to   the
    defendant, bears at least substantially equal responsibility for
    the wrong he seeks to redress and (ii) preclusion of the suit would
    not interfere with the purposes of the underlying law or otherwise
    contravene the public interest."             Nisselson v. Lernout, 
    469 F.3d 143
    , 152 (1st Cir. 2006); see Bateman Eichler, Hill Richards, Inc.
    v. Berner, 
    472 U.S. 299
    , 310-11 (1985).
    We reject Gattineri's arguments.               Gattineri was in pari
    delicto with Wynn Defendants because he knew everything that he
    needed to know to deduce that the San Diego Agreement may violate
    public policy.           He was aware of the Commission's decision to
    require the Certificate, knew the Commission was concerned about
    the   sale   of    the    Parcel   (indeed,      he   was    interviewed     by   the
    Massachusetts State Police and was subpoenaed for testimony before
    - 37 -
    the agreement was signed), understood the Commission's signature
    requirement was meant to assuage those concerns, recognized that
    the gaming industry is highly regulated, and was being advised by
    counsel at all pertinent steps.    Taken together, this should have
    given Gattineri pause as to whether the San Diego Agreement would
    be legally enforceable.     Gattineri maintains that Wynn Defendants
    were far more experienced in the gaming industry, and he trusted
    that they would negotiate an agreement that was legal, but as a
    sophisticated businessman who was being advised by counsel, he
    cannot hide behind Wynn Defendants to claim excusable ignorance.
    There is simply no triable issue of differential knowledge that
    would make the doctrine of in pari delicto applicable here.
    F. Legality of the Alleged San Diego Agreement
    Having rejected some of the alternative grounds on which
    the district court granted summary judgment, we next address the
    legality of the alleged San Diego Agreement.       This question is
    dispositive of this suit.    If the agreement violates state law or
    public policy, Gattineri's contract and fraud claims cannot move
    forward. Ultimately, we conclude that no controlling SJC precedent
    exists to guide our analysis and thus certify the questions
    outlined below to the SJC.
    Under Massachusetts law, a contract is unenforceable if
    "illegality constitutes an essential element of the contract."
    Health Care Collection Servs., Inc. v. Protocare, Inc., No. CIV.
    - 38 -
    A. 92-12634-Z, 
    1995 WL 96911
    , at *2 (D. Mass. Feb. 24, 1995) (first
    citing Green v.    Richmond, 
    337 N.E.2d 691
    , 695 (Mass. 1975),
    abrogated on other grounds by Wilcox v. Trautz, 
    693 N.E.2d 141
    (Mass. 1998); and then citing Zytka v. Dmochowski, 
    18 N.E.2d 332
    ,
    334 (Mass. 1938), abrogated on other grounds by Wilcox, 
    693 N.E.2d 141
    ).   A contract can be deemed illegal if it expressly violates
    a statute or, even if it does not, if finding it unenforceable is
    "necessary to accomplish the statute's objectives."                Baltazar
    Contractors, Inc. v. Town of Lunenburg, 
    843 N.E.2d 674
    , 677 (Mass.
    App. Ct. 2006); see also Serv. Emps. Int'l Union v. Dep't of Mental
    Health, 
    63 N.E.3d 1097
    , 1102 (Mass. 2016) ("[W]hether a contract
    made in violation of a statute is rendered void ab initio, i.e.,
    treated as having no force or effect, depends upon the language of
    the statute and the nature of the violation.").
    In   other   words,   Massachusetts   law   will   not   enforce
    contracts that disregard public policy, Trs. of Cambridge Point
    Condo. Tr. v. Cambridge Point, LLC, 
    88 N.E.3d 1142
    , 1150 (Mass.
    2018), where "public policy" "refers to a court's conviction,
    grounded in legislation and precedent, that denying enforcement of
    a contractual term is necessary to protect some aspect of the
    public welfare," Beacon Hill Civic Ass'n v. Ristorante Toscano,
    Inc., 
    662 N.E.2d 1015
    , 1017 (Mass. 1996).       "The test is, whether
    the underlying tendency of the contract under the conditions
    described was manifestly injurious to the public interest and
    - 39 -
    welfare."     
    Id.
     (quoting Adams v. East Boston Co., 
    127 N.E. 628
    ,
    631 (Mass. 1920)).          However, "[t]he grounds for a public policy
    exception must be clear in the acts of the Legislature or the
    decisions of [a Massachusetts] court."               Cambridge Point, LLC, 88
    N.E.3d at 1150 (quoting Miller v. Cotter, 
    863 N.E.2d 537
    , 547
    (Mass. 2007)).
    Here, we are asked to determine first, whether the
    alleged contract violates Chapter 23K of the Massachusetts General
    Laws   and    second,    if     not,     whether   it   nonetheless    violates
    Massachusetts        public     policy,     rendering     it   unenforceable.
    Chapter 23K sections 21(b) and (c) provide in relevant part:
    (b) No person shall transfer a
    gaming license, a direct or indirect real
    interest, structure, real property, premises,
    facility, personal interest or pecuniary
    interest under a gaming license issued under
    this chapter or enter into an option contract,
    management contract or other agreement or
    contract providing for such transfer in the
    present or future, without the notification
    to, and approval by, the [C]ommission.
    . . .
    (c) The [C]ommission may include any
    reasonable additional requirements to the
    license conditions.
    Mass. Gen. Laws ch. 23K, § 21(b), (c) (emphases added).
    The district court found that the alleged San Diego
    Agreement constitutes an "unenforceable illegal contract" under
    Chapter 23K    for    two     reasons.      First,   because   the    Commission
    "specific[ally] approv[ed]" a "price reduction to 'no more [than]
    - 40 -
    $35 million,'" and the alleged San Diego Agreement "effectively
    reinstat[es]      the   $75 million     purchase     price      with   respect   to
    Gattineri without the Commission's approval."                  Gattineri, 
    2022 WL 123892
    , at *11 (third alteration in the original). Second, because
    the "basis of the agreement [was] Gattineri's signing of the
    [C]ertificate, which was a requirement mandated by the Gaming
    Commission,"      and   using   the   signing   of       the    [C]ertificate     as
    consideration for a contract, constitutes an "other agreement" for
    the "transfer" of a "personal or pecuniary interest under a gaming
    license," 
    id.,
     in direct violation of Chapter 23K since it was
    made       "without[]   notification      to,      and     approval      by,     the
    [C]ommission" as required by the statute, 
    id.
     (first alteration in
    original) (quoting Mass. Gen. Laws. ch. 23K, § 21(b), (c)).
    Gattineri argues on appeal that the alleged contract is
    not illegal.2     It does not violate Chapter 23K, he posits, because
    he is not bound by section 21(b) of the Gaming Act.                    In fact, he
    is "not bound by any requirement from the Commission," he contends,
    Gattineri also argues that the district court reached the
    2
    conclusion that the alleged San Diego Agreement violated the
    statute based on disputed material facts.          We reject this
    reasoning.   The district court relied on the language of the
    Commission in approving the Ninth Amendment, the terms of the
    alleged San Diego Agreement, and the plain language of the
    statute -- none of which were in dispute -- in making its
    determination. Because the district court's conclusion was a pure
    question of law, the crux of the issue lies in whether the district
    court's interpretation of the Gaming Act was accurate, not on
    disputed facts.
    - 41 -
    because he is not a licensee, nor was he a party to the Ninth
    Amendment.    Pointing to the "under a gaming license" language in
    the statute, he argues that he does not fall within the class of
    people the statute seeks to cover since he himself had no interest
    in obtaining a gaming license.
    Wynn Defendants counter that the alleged contract not
    only violates Chapter 23K but also contravenes public policy.               As
    to the statutory violation, they counter that Gattineri is covered
    by the statute because, although not a licensee, the plain language
    of sections 21(b) and (c) covers "person[s]" more generally since
    it dictates that "no person" shall enter into an "agreement"
    without the Commission's approval.            Mass. Gen. Laws. ch. 23K,
    § 21(b).     Gattineri, they argue, is certainly a "person" who
    engaged in an alleged agreement (the San Diego Agreement) that was
    not approved by the Commission.      They further contend that even if
    that were not the case, whether Gattineri can be considered a
    licensee is irrelevant because the Commission imposed conditions
    on   Wynn    Defendants   and   these      conditions   should     cover   any
    transactions they engaged in, in relation to the license they
    sought, including a side deal with Gattineri.           Additionally, they
    assert that the side deal violates public policy because it
    "thwart[s] the Legislature's express statutory purpose" -- "to
    ensure   public   confidence    in   the    integrity   of   the    licensing
    process" -- by going against the Commission's "broad authority to
    - 42 -
    condition the casino license on a reduced purchase price for the
    Parcel, and restrict the recipients of the sale proceeds."            This
    type of agreement, Wynn Defendants argue, "is precisely the kind
    of conduct the Legislature sought to prevent in enacting the Gaming
    Act."
    Thus, the questions before us are ones of statutory
    construction of state law and of Massachusetts public policy.          In
    essence, the parties ask us to determine whether (1) the regulation
    of a side deal and the purchase price of a parcel of land between
    two private parties, in light of potential concealed, criminal
    ownership    interests    and/or    environmental   concerns,    expressly
    violates Chapter 23K; or, whether, in the alternative, (2) this
    "underlying    tendency     of     the   contract . . . was     manifestly
    injurious to the public interest and welfare," Beacon, 662 N.E.2d
    at 1017, as to be against public policy under the acts of the
    legislature or decisions of the Massachusetts courts.
    While we would generally look to the text of the statute,
    intent of the legislature, and case law to address these issues,
    our de novo examination of the statutory scheme and the lack of
    precedent available to guide our analysis leads us to conclude
    that the best course to resolve these questions is to certify this
    issue.   VanHaaren v. State Farm Mut. Auto. Ins. Co., 
    989 F.2d 1
    ,
    3 (1st Cir. 1993) ("Absent controlling state court precedent, a
    federal court sitting in diversity may certify a state law issue
    - 43 -
    to the state's highest court."); see e.g., Bos. Gas Co. v. Century
    Indem. Co., 
    529 F.3d 8
    , 15 (1st Cir. 2008) (certifying question
    because    court       "found    no     controlling      SJC     precedent     on
    the . . . question and the issue is determinative of the scope of
    [the] claim)," certified question answered, 
    910 N.E.2d 290
     (Mass.
    2009).
    Massachusetts SJC Rule 1:03 provides that the SJC "may
    answer questions of law certified to it" where the question "may
    be determinative of the cause then pending in the certifying court
    and . . . it appears to the certifying court [that] there is no
    controlling precedent in the decisions of [the SJC]." Mass. S.J.C.
    R. 1:03.   That is certainly the case here.             There is no question
    that the questions we certify are determinative of the issues
    before us, so we next address the text of the Gaming Act and lack
    of precedent.
    1. The Gaming Act
    Looking to the text of the Gaming Act, it is unclear how
    much authority the Massachusetts legislature sought to give the
    Commission.     Enacted in 2011, the Gaming Act created a structured
    process for licensing and regulating casino and slots gambling in
    Massachusetts, thereby authorizing these activities for the first
    time in the Commonwealth.         Mass. Gen. Laws. ch. 23K; see Abdow v.
    Att'y Gen., 
    11 N.E.3d 574
    , 577 (Mass. 2014) (summarizing text of
    the   Gaming   Act).      In    doing   so,    the   Gaming    Act   created   and
    - 44 -
    authorized the Massachusetts Gaming Commission -- comprised of
    five    appointed     Commissioners          with       expertise          in    criminal
    investigation      and     law     enforcement,          corporate         finance     and
    securities, and legal and policy issues -- to issue two types of
    licenses to operate gaming establishments.                          Mass. Gen. Laws.
    ch. 23K,    § 3.      It   also    established          the   IEB    as    the   primary
    enforcement agent endowed with "such law enforcement powers as
    necessary to effectuate the purposes" of the Gaming Act.                               Id.
    § 6(a)-(b).
    On the one hand, sections of the Gaming Act seem to grant
    the Commission extensive authority to administer gaming in the
    Commonwealth.      For instance, section 21 -- which outlines the form
    of gaming and conditions for licensees -- appears to give the
    Commission wide latitude in restricting the issuance of licenses
    since    subsection      (c)   allows      the    Commission        to    "include     any
    reasonable additional requirements to the license conditions."
    Id.    § 21(c)   (emphasis       added).         This   language         suggests    that,
    notwithstanding the conditions already listed, the Commission
    should be entitled to institute any other restrictions it deems
    necessary.       Similarly,       section    17 -- which        explains         how   the
    Commission should process applications -- gives the Commission
    "full discretion as to whether to issue a license," id. § 17(g)
    (emphasis added), and "sharply curtail[s] the availability of
    judicial review of [C]ommission licensing decisions . . . thereby
    - 45 -
    vest[ing] a tremendous amount of discretion in the [C]ommission,"
    City   of   Revere    v.    Mass.    Gaming    Comm'n,   
    71 N.E.3d 457
    ,   471
    (Mass. 2017).     What is more, section 4, outlining the powers of
    the Commission, explicitly states that "[t]he [C]ommission shall
    have all powers necessary or convenient to carry out and effectuate
    its    purposes      including,      but   not    limited     to,      the   power
    to: . . . limit, condition, restrict, revoke or suspend a license,
    registration, finding of suitability or approval, or fine a person
    licensed, registered, found suitable or approved for any cause
    that the [C]ommission deems reasonable." Mass. Gen. Laws. ch. 23K,
    § 4(15)     (emphasis      added).     Further,    section    1,    which    lists
    Chapter 23's findings and declaration, ends by stating that "the
    power and authority granted to the [C]ommission shall be construed
    as broadly as necessary for the implementation, administration and
    enforcement" of the Gaming Act.               Id. § 1(10) (emphasis added).
    These provisions, included in key sections of the Gaming Act, seem
    to serve as catchall provisions giving the Commission authority to
    place restrictions on side deals and the purchase price of land,
    and to place conditions on certain applicants (i.e., perhaps
    greater      restrictions       on    those      with    potential       criminal
    backgrounds).
    On the other hand, the Gaming Act's policy objectives
    could be interpreted as placing limits on what otherwise might be
    considered broad authority, but the intent of the Commonwealth
    - 46 -
    legislature     remains    unclear.     Section 1   provides   that   the
    "paramount policy objective" of the Gaming Act is to "ensur[e]
    public confidence in the integrity of the gaming licensing process
    and in the strict oversight of all gaming establishments through
    a rigorous regulatory scheme."        Id. § 1(1) (emphasis added).     In
    other words, even if we agree that the Commission does have
    extensive authority to regulate side deals (which we do not hold
    here), this authority is limited to that which ensures public
    confidence in licensing (or perhaps another policy objective we
    may find in the Act).       Thus, our task is to determine whether the
    restrictions here ensure public confidence.         But policy arguments
    do not "line up solely behind one solution,"          Bos. Gas Co., 
    529 F.3d at 14
    , and the parties do not point to any case law in either
    federal or state court interpreting section 21, the breadth of the
    authority of the Commission, or Massachusetts's public policy on
    these issues.    The only case that does tangentially touch on these
    issues (discussed below) further complicates our inquiry but does
    not resolve it.
    2. Lack of Precedent
    Published after the district court issued its decision
    and Gattineri filed this appeal (but before oral argument), FBT
    Everett Realty, LLC       v. Mass. Gaming Comm'n, 
    187 N.E.3d 373
     (Mass.
    2022), further muddles the district court's interpretation of
    section 21, rather than resolve the issues before us.          There, the
    - 47 -
    SJC considered a suit by FBT against the Commission to recover the
    lost $40 million premium from the sale of the Parcel, alleging
    tortious interference with contract and a regulatory taking.                  Id.
    at 378.    The SJC held that the state court properly dismissed the
    tortious inference claim but reversed the court's grant of summary
    judgment on the regulatory takings claim because the lower court
    failed to consider the "economic impact and the character of the
    government action," two of the three factors in the multifactor
    test for a regulatory taking.           Id. at 382, 392.       Ultimately, the
    SJC did not hold for either party and instead concluded that
    "summary judgment [could not] be granted on [the] record" as there
    were "material disputed facts on exactly what the [C]ommission
    expected or required Wynn [MA, LLC] to do, and what [it] did on
    its own initiative."         Id. at 378.
    While FBT does not resolve the issues before us, the SJC
    did    raise    noteworthy    concerns     regarding   the    conduct    of   the
    Commission,       illustrating    the    importance    of     certifying      our
    questions.       For instance, in assessing the economic impact and
    character of the government action, the SJC noted that some of the
    Commission's actions were "highly unusual [in] character."                Id. at
    388.    While not directly addressing the text of Chapter 23K, the
    court questioned the fact that the Commission (1) did not fully
    investigate       "the   possibility     that   someone      with   a   criminal
    background" may have had an "undisclosed ownership interest in the
    - 48 -
    [P]arcel" or (2) consider other options in resolving this issue
    such       as    "refus[ing]      to    consider    Wynn's       bid    altogether"     or
    "reject[ing] Wynn's bid if it could not resolve the ownership issue
    to     [the      Commission's]         satisfaction,"      before       it   approved     a
    significantly           reduced     purchase       price    for        the   Parcel -- a
    "multimillion-dollar windfall at the expense of another private
    party."          Id.    at   386-87.       While    the    SJC   did     note   that    the
    "[C]ommission ha[s] broad discretion in addressing its concerns
    about potential concealed, criminal ownership interests in FBT,"
    it   did        not    provide    guidance    as    to    the    boundaries     of     that
    discretion, nor did it hold that the Commission had the power to
    "punish one party for its lack of candor," "ensure [that] such
    persons do not reap a financial windfall from the award of a gaming
    license," or "address the public perception that this was even a
    possibility."           Id. at 387 (emphasis added).
    Gattineri argues3 that FBT should control our decision
    in this contract dispute.               Nonetheless, FBT does not resolve this
    case since it was adjudicated at the summary judgment stage viewing
    the facts in the light most favorable to the non-moving party,
    FBT; did not ultimately resolve the dispute as a matter of law
    given the limited record; and contrary to Gattineri's assertion,
    made no holding as to the legality of side deals in connection
    Gattineri made this argument at oral argument and in his
    3
    reply brief, submitted after FBT was published.
    - 49 -
    with the statute and parties now in question.           The cause of action
    in FBT is simply not the one before us.         Even though FBT does not
    resolve our case, it does counsel in favor of certification.             We
    simply   cannot   ignore   that   the   SJC   found    "extraordinary"   the
    "[c]onditioning [of] the grant of a governmental license [the
    gaming license at issue here] on the renegotiation of a transaction
    between private parties [Wynn Defendants and FBT] in this way, so
    as to effectively transfer $40 million dollars from one [party,
    here FBT] to another [Wynn Defendants]."         Id.
    3. Questions Certified
    We must underscore that the issues before us involve
    important questions of state law and public policy with significant
    implications, not only for the parties before us, but also for
    other industries in the state, such as online gambling and horse
    racing, among others.       "Given the social evils associated with
    gambling and the state's revenue interests, the state's choice of
    means in the selection of licensees is entitled to prevail," Medina
    v. Rudman, 
    545 F.2d 244
    , 251 (1st Cir. 1976), and so too the
    highest court's (the SJC) careful balancing of the legislature's
    statutory scheme.
    This case then meets the requirements set forth in SJC
    Rule 1:03.   Mass. S.J.C. R 1.03.       We recognize that our answering
    the important policy questions raised in this appeal "may offend
    the comity due to local courts, since [Massachusetts] courts have
    - 50 -
    never addressed this specific issue."               Santiago-Hodge v. Parke
    Davis & Co., 
    859 F.2d 1026
    , 1033 (1st Cir. 1988).                        Thus, the
    questions specified below will be referred to the Massachusetts
    SJC for its consideration.          We have addressed all other issues,
    confirming    that     the    certified    issues   do   affect    the    ultimate
    outcome.     The questions are as follows:
    1) Is the San Diego Agreement unenforceable
    because it violates Section 21 of the Gaming
    Act?
    2) If not, is the San Diego Agreement
    unenforceable for reasons of public policy of
    ensuring public confidence in the integrity of
    the gaming licensing process and in the strict
    oversight of all gaming establishments through
    a rigorous regulatory scheme?
    We    also   welcome    any    additional     observations       about    relevant
    Massachusetts law that the SJC may wish to provide.
    The clerk of this court is directed to forward to the
    SJC, under the official seal of this court, a copy of the certified
    questions and our decision in this case, along with a copy of the
    briefs and appendices filed by the parties in this case.                 We retain
    jurisdiction over this appeal and will frame our ultimate decision
    and   judgment   after       receiving    such   guidance   on    the    certified
    questions as the SJC may be prepared to give.                No costs will be
    taxed at this stage of the proceedings, but the issue may be
    revisited after we receive the answer to the certified questions.
    It is so ordered.
    - 51 -