Court Opinion

ID: 9381450
Source: CourtListenerOpinion
Date Created: 2023-03-22 21:00:50.997761+00
Date Added: 2024-06-11T17:17:32.633421
License: Public Domain

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").

                                    - 3 -
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.

                                     - 4 -
           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

                                         - 7 -
           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

                               - 12 -
           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

                              - 13 -
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.

                             - 16 -
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 -