Court Opinion

ID: 9555720
Source: CourtListenerOpinion
Date Created: 2023-08-14 21:00:18.986817+00
Date Added: 2024-06-11T15:41:31.227751
License: Public Domain

United States Court of Appeals
                     For the First Circuit

No. 21-1421

                    UNITED STATES OF AMERICA,

                            Appellee,

                               v.

                     WILLIAM McGLASHAN, JR.,

                      Defendant, Appellant.

          APPEAL FROM THE UNITED STATES DISTRICT COURT
               FOR THE DISTRICT OF MASSACHUSETTS

         [Hon. Nathaniel M. Gorton, U.S. District Judge]

                             Before

                  Gelpí, Howard, and Thompson,
                        Circuit Judges.

     Carter G. Phillips, with whom Jack W. Pirozzolo, Daniel J.
Feith, John L. Gibbons, Sidley Austin LLP, John C. Hueston, and
Hueston Hennigan LLP were on brief, for appellant.
     Alexia R. De Vincentis, Assistant United States Attorney,
with whom Nathaniel R. Mendell, Acting United States Attorney, was
on brief, for appellee.

                         August 14, 2023
             HOWARD, Circuit Judge.            In this appeal involving the

scope   of    the    federal    wire   fraud    statute,     18   U.S.C.    § 1343,

defendant-appellant William McGlashan, Jr., argues in part that

the indictment against him should have been dismissed for aiming

at a property interest that was not the object of his fraud.                     We,

however,     conclude    that    the   relevant      property     alleged   in   the

indictment was indeed an object of his fraud, and McGlashan's other

arguments either are superfluous to our decision or have been

waived.      We therefore affirm the judgment of the district court.

                                        I.

             We     briefly     summarize      the   factual      background     and

procedural posture of the case, as relevant to McGlashan's appeal.

"Ordinarily, because this appeal follows a guilty plea, we would

derive the facts from the plea agreement, the change-of-plea

colloquy,      the     unchallenged      portions       of      the     presentence

investigation report, and the sentencing hearing transcript."

United States v. Parigian, 824 F.3d 5, 8 (1st Cir. 2016); see also

United States v. Díaz-Rivera, 957 F.3d 20, 22 (1st Cir. 2020).

However, "because [McGlashan's] appeal trains solely on the legal

adequacy of the challenged superseding indictment, we focus our

review within th[at] indictment's four corners."                      Parigian, 824

F.3d at 8.

                                       - 2 -
                                         A.

                Along with fourteen other parents, McGlashan was named

as a defendant in an indictment that resulted from "Operation

Varsity Blues" (the "Operation"), an investigation into alleged

fraudulent schemes designed to secure the defendants' children's

admission to elite universities throughout the United States.                As

is most relevant to this appeal, McGlashan's involvement in the

scheme charged in this case boils down to paying $50,000 to have

an ACT proctor change his son's test answers in order to increase

his son's ACT score.1

                The ACT exam is a "standardized test that is widely used

as part of the college admissions process in the United States,"

and   is    run     by    ACT,   Inc.   ("ACT"),   an   Iowa-based    nonprofit

organization.            As noted in the indictment, "[m]ost selective

colleges and universities in the United States require prospective

students to submit standardized test scores . . . as part of their

application packages," and these "scores are a material part of

the admissions process."          The ACT exam is administered by proctors

who       the      indictment      alleges      "are    agents       of   ACT[,

Inc.][,] . . . [who] owe a duty of honest services to th[at]

      1The indictment also alleges that McGlashan participated in
a scheme to falsify his son's athletic credentials in an attempt
to have him admitted to the University of Southern California
("USC") as a "purported football recruit." However, this scheme
is not at issue in the instant appeal because McGlashan only
pleaded guilty to the ACT-related fraud.

                                        - 3 -
organization[]."       Before administering the exam, the proctors

"must   typically     certify"    that      they    will   abide   by    the    ACT

Administration Manual and "ensure that 'the test materials are

kept secure and confidential, used [by each] examinee only, and

returned   to   ACT   immediately       after      testing.'"      The   exam    is

"typically administered to large groups of students on specified

dates and under strict time limits," but "students with certain

learning   or    other    disabilities          may    qualify     for   testing

accommodations, . . . and, in such circumstances, may take the

test alone, under the supervision of a test administrator retained

by ACT, Inc. . . . ."

           The indictment alleges that McGlashan agreed in fall

2017 to direct $50,000 to a nonprofit corporation founded by

William "Rick" Singer -- the principal organizer of the schemes

implicated in the Operation            -- as a "purported donation"              in

exchange for Singer arranging for a test proctor who would correct

his son's exam answers.          Singer instructed McGlashan to send a

"Request for Arranged Testing" form to ACT, so that McGlashan's

son would take the exam at a school in West Hollywood, California,

rather than at his own high school.             Having McGlashan's son take

the ACT exam at the West Hollywood school was crucial to the plan,

since it is alleged that Singer "bribed" Igor Dvorskiy -- the

director   of   the   school     and   "a   compensated     standardized       test

administrator for ACT, Inc." -- to allow a proctor to correct

                                       - 4 -
McGlashan's son's test answers.         Singer did so by "caus[ing]" the

same nonprofit to which McGlashan had directed the $50,000 to pay

both Dvorskiy and the proctor for their role in "facilitating [the]

cheating."

             All went to plan, at least initially.           McGlashan's son

took the ACT exam at the West Hollywood school on December 9, 2017,

and    the   test   proctor   duly   corrected    his    answers   thereafter.

Dvorskiy sent the exam materials to ACT's Iowa headquarters several

days later via Federal Express.        Singer then paid Dvorskiy $40,000

and the proctor $35,000 through the above-mentioned nonprofit

later that month for their respective services "for McGlashan's

son and other students."         After his son's ACT score was released

in early January, McGlashan texted Singer that "[y]ou have a very

relieved and motivated young man!          Very grateful."     The score was

ultimately sent to several colleges -- including Northeastern

University, located in Massachusetts -- on October 24, 2018.

                                      B.

             On January 14, 2020, a grand jury sitting in the District

of    Massachusetts    charged   McGlashan   in    the    Fourth   Superseding

Indictment -- the operative indictment in this appeal -- with (1)

conspiracy to commit mail and wire fraud, in violation of 18 U.S.C.

§ 1349 (Count One); (2) conspiracy to commit federal programs

bribery prohibited by 18 U.S.C. § 666(a)(2), in violation of 18

U.S.C. § 371 (Count Two); (3) money laundering conspiracy, in

                                     - 5 -
violation of 18 U.S.C. § 1956(h) (Count Three); and (4) wire fraud

and honest services wire fraud, and aiding and abetting the same,

in violation of 18 U.S.C. §§ 1343, 1346, and 2 (Count Seven).

Count Seven specifically alleges -- as is most relevant to this

appeal -- that McGlashan:

             having devised and intending to devise a
             scheme and artifice to defraud and for
             obtaining   money    and   property,   to  wit,
             ACT . . . standardized      tests    and   test
             scores, . . . by means of materially false and
             fraudulent pretenses, representations, and
             promises, and to defraud and deprive [] ACT,
             Inc., . . . of [its] right to the honest and
             faithful     services      of     [its]    test
             administrators . . . through      bribes    and
             kickbacks, did transmit and cause to be
             transmitted, by means of wire communications
             in interstate and foreign commerce, writings,
             signs, signals, pictures and sounds for the
             purpose of executing the scheme to defraud[:]
             [the   "ACT   scores    sent   to  Northeastern
             University" on or around October 24, 2018].

Thus,   in   Count   Seven,   the   indictment   alleges   that   McGlashan

participated in a fraudulent scheme to obtain tests and test scores

from ACT, and that, through bribes and kickbacks, he sought to

deprive ACT of the "honest services" of its test administrators.

             In moving to dismiss Count Seven, McGlashan advanced

three arguments related to the allegations of fraud against ACT:

(1) ACT test scores cannot constitute "money or property" under

the wire fraud statute, because they do not constitute items that

have "long been recognized as property," Carpenter v. United

                                    - 6 -
States,   484   U.S.   19,   26    (1987);      (2)    the   indictment    did   not

adequately allege a scheme to obtain standardized tests; and (3)

the indictment's description of Dvorskiy's responsibilities as an

ACT   test    administrator       did    not    give    rise    to   a    fiduciary

relationship for purposes of the honest-services theory.                         The

district court denied his motion.

             McGlashan ultimately entered a conditional guilty plea

to Count Seven on February 10, 2021. His plea agreement stipulated

that he pleaded guilty to that count "insofar as [it] charges a

scheme and artifice to defraud ACT, Inc., of standardized tests

and test scores, and of its right to the honest and faithful

services of its test administrators."                   Nevertheless, the plea

agreement preserved McGlashan's right to appeal the denial of his

motion to dismiss the indictment based on the following arguments:

             [F]irst, that test scores cannot, as a matter
             of law, constitute property for purposes of
             the mail or wire fraud statutes, and that, to
             the extent that standardized tests might be
             considered property under the mail or wire
             fraud statutes, the indictment did not
             adequately allege facts establishing a scheme
             to fraudulently obtain standardized tests in
             this case; and second, that the indictment did
             not adequately allege facts establishing that
             test administrators owed a fiduciary duty to
             testing companies in this case.

The agreement allows McGlashan to withdraw his guilty plea should

his appeal succeed.     This appeal followed.

                                        - 7 -
                                  II.

           "In reviewing a district court's denial of a motion to

dismiss an indictment, we review legal questions de novo, any

relevant   factual   findings   for   clear   error,   and   the       court's

'ultimate ruling' for abuse of discretion."      Parigian, 824 F.3d at

9 (quoting United States v. Doe, 741 F.3d 217, 226 (1st Cir.

2013)).    Whether the facts put forth in an indictment suffice to

allege a federal crime is a question of law that we review de novo.

See United States v. Brissette, 919 F.3d 670, 676 (1st Cir. 2019)

("'Because the district court's ruling was a legal determination

based on its interpretation of [a federal criminal statute] and

relevant case law,' we proceed to 'reviewing the District Court's

conclusion de novo.'" (cleaned up) (first quoting United States v.

Hall, 20 F.3d 1084, 1088 (10th Cir. 1994), then quoting United

States v. Musso, 914 F.3d 26, 30 (1st Cir. 2019))).

           As   earlier   observed,   Count   Seven    charges     a    scheme

incorporating two theories of wire fraud: (1) a scheme and artifice

to defraud ACT of its test and test scores under 18 U.S.C. § 1343,

and (2) a scheme or artifice to deprive ACT of its right to the

honest services of its test administrators under 18 U.S.C. § 1346.

We need only find one of these theories valid to affirm the

judgment of the district court.       Cf. United States v. Abdelaziz,

68 F.4th 1, 26 n.14 (1st Cir. 2023) ("[W]hen the government has

advanced several alternate theories of guilt and the trial court

                                 - 8 -
has submitted the case to the jury on that basis, an ensuing

conviction may stand as long as the evidence suffices to support

any one of the submitted theories." (quoting United States v.

Celestin, 612 F.3d 14, 24 (1st Cir. 2010))); United States v.

Ayala, 289 F.3d 16, 22 (1st Cir. 2002) ("[C]onvictions generally

have been sustained as long as the proof upon which they are based

corresponds   to       an   offense    that    was   clearly   set   out   in   the

indictment.        A    part   of     the   indictment    unnecessary      to   and

independent of the allegations of the offense proved may normally

be treated as a useless averment that may be ignored." (quoting

United States v. Miller, 471 U.S. 130, 136 (1985))).

                                        III.

          McGlashan's challenge to the indictment's first wire

fraud theory rests on two grounds.               First, he contends that ACT

scores cannot constitute "money or property" for purposes of the

wire fraud statute.         Second, he asserts that the indictment does

not adequately allege a scheme having the object of obtaining

standardized tests.         In challenging the second theory, he argues

that "informal" fiduciary relationships of the variety that the

indictment alleges Dvorskiy had with ACT do not suffice for the

purposes of honest services wire fraud.              As noted above, if any of

the grounds advanced by McGlashan fails, then the indictment is

legally sufficient and the conviction stands.              We therefore bypass

the challenge based on the argument that ACT scores are not

                                        - 9 -
"property" as contemplated by the statute and train our analysis

on   the   more      straightforward     issues    of     whether   attaining   ACT

standardized tests is adequately alleged as a legally sufficient

object     of     the   scheme    and    whether     a     cognizable     fiduciary

relationship has been alleged.2

                                          A.

              The federal wire fraud statute prohibits "any scheme or

artifice to defraud, or for obtaining money or property by means

of false or fraudulent pretenses, representations, or promises"

through interstate or foreign wires.              18 U.S.C. § 1343.        In order

to prove a violation of the statute, the government must show "(1)

a    scheme     or   artifice    to   defraud     using    false    or   fraudulent

pretenses; (2) the defendant's knowing and willing participation

in the scheme or artifice with the intent to defraud; and (3) the

use of the interstate wires in furtherance of the scheme."                   United

States v. Pena, 910 F.3d 591, 596 (1st Cir. 2018) (quoting United

States v. Appolon, 715 F.3d 362, 367 (1st Cir. 2013)).                           In

       2We also opt not to address McGlashan's first argument in
recognition of the fact that the legal landscape with regard to
the scope of property rights protected by the wire fraud statute
has significantly changed since the parties addressed the issue in
their briefing to us, most notably through the Supreme Court's
decision in Ciminelli v. United States, 143 S. Ct. 1121 (2023),
and our own court's decision in Abdelaziz. See also PDK Lab'ys,
Inc. v. U.S. Drug Enf't Admin., 362 F.3d 786, 799 (D.C. Cir. 2004)
(Roberts, J., concurring) ("[T]he cardinal principle of judicial
restraint -- if it is not necessary to decide more, it is necessary
not to decide more -- counsels us to go no further.").

                                        - 10 -
addition, despite the statute's use of the disjunctive "or" between

the phrases "any scheme or artifice to defraud" and "for obtaining

money or property," the Supreme Court has "[c]onstru[ed] that

disjunctive phrase as a unitary whole" and "held that 'the money-

or-property requirement of the latter phrase' also limits the

former."    Kelly v. United States, 140 S. Ct. 1565, 1571 (2020)

(quoting McNally v. United States, 483 U.S. 350, 358 (1987),

superseded by statute as recognized in Percoco v. United States,

143 S. Ct. 1130, 1136 (2023)).          "The wire fraud statute thus

prohibits only deceptive 'schemes to deprive [the victim of] money

or property.'"   Id. (alteration in original) (quoting McNally, 483

U.S. at 356).

            McGlashan   contends     that   the   indictment    did   not

adequately allege a scheme to defraud ACT of its standardized

tests.     Relying on Kelly, he submits that the exam was a "mere

implementation cost" of his scheme, and not an "object of the

fraud."

            In Kelly, the Supreme Court reversed the wire fraud

convictions of New Jersey public officials who -- in a scandal

commonly known as "Bridgegate" -- aimed to punish the mayor of

Fort Lee, New Jersey, "for refusing to support the New Jersey

Governor's reelection bid" by reducing the number of lanes of the

George Washington Bridge dedicated to traffic from Fort Lee from

three to one.     Kelly, 140 S. Ct. at 1568, 1570.             The scheme

                                   - 11 -
necessitated hiring backup toll collectors who could operate a

toll booth during the on-duty collector's breaks, in order to

ensure that the single remaining lane would remain continuously

open.   Id. at 1570.   The officials also concocted a traffic study

to cover up the scheme; this study required the hiring of traffic

engineers.   Id.   The government's wire fraud theory was predicated

in part on the idea that the "defendants aimed to deprive the Port

Authority [of New York and New Jersey (i.e., the government agency

in charge of the bridge)] of the costs of compensating the traffic

engineers and back-up toll collectors who performed work relating

to the lane realignment."   Id. at 1572.   A unanimous Court rejected

this theory, since "property must play more than some bit part in

a scheme: it must be an 'object of the fraud.' . . . [A] property

fraud conviction cannot stand when the loss to the victim is only

an incidental byproduct of the scheme."        Id. at 1573 (quoting

Pasquantino v. United States, 544 U.S. 349, 355 (2005)). The Court

found that the "time and labor" of the engineers and backup toll

collector did not constitute an object of the fraud, because

"[n]either defendant sought to obtain the services that the[se]

employees provided"; they "did nothing [the defendants] thought

useful."     Id. at 1573-74.    The Court explicitly held so with

federalism concerns in mind:

           Every regulatory decision . . . requires the
           use of some employee labor. But that does not
           mean every scheme to alter a regulation has

                                - 12 -
            that labor as its object. . . . To rule
            otherwise would undercut this Court's oft-
            repeated instruction: Federal prosecutors may
            not use property fraud statutes to "set[]
            standards of disclosure and good government
            for local and state officials."

Id. at 1574 (alteration in original) (quoting McNally, 483 U.S. at

360).

            McGlashan urges us to find that obtaining the ACT score

was the sole object of his scheme, to the exclusion of the ACT

exam itself.    He points to the indictment's allegation that one of

the "principal purposes" of the scheme was "securing the admission

of   the    defendants'   children   to   selective   colleges    using

fraudulently obtained test scores" to support his claim.         In his

view, much like the extra toll collectors and engineers' time and

labor in Kelly, gaining access to the ACT test was "'needed' to

realize the final plan" but ultimately a mere "implementation

cost[]" of the scheme.      Id. at 1574.     He posits that he "was

indifferent to obtaining the ACT exam as such," and points out

that his son could have simply accessed the test at his high

school.

            We find McGlashan's arguments unpersuasive, and agree

with the government that they "suffer[] from two fundamental

flaws."    First, as the Second Circuit has concluded, "[d]efendants

may have . . . multiple objectives, but property need only be 'an

object' of their scheme, not the sole or primary goal."          United

                                - 13 -
States v. Gatto, 986 F.3d 104, 116 (2d Cir. 2021) (emphasis in

original) (quoting Kelly, 140 S. Ct. at 1572). Second, and perhaps

more    importantly,     McGlashan's        arguments       also    inappropriately

downplay the Kelly Court's emphasis on what the defendant "sought"

in     differentiating      objects    of     the    fraud     from        "incidental

byproduct[s]" or mere "implementation costs[.]"                    Kelly, 140 S. Ct.

at 1574.

            Mindful    of    these    precepts,      and     employing       the    same

holistic    analysis     that   the   Supreme       Court    used     in    Kelly    (as

McGlashan concedes) to parse the objects of his scheme, we are

left with little doubt that the indictment adequately alleges that

the ACT test was an object of the fraud.                    Kelly, 140 S. Ct. at

1574.      The indictment provides ample evidence to support the

proposition that McGlashan actively sought to obtain the ACT test

in the way Singer had devised, and not just the scores.                       To that

end, the $50,000 that he spent for the scheme covered not only the

cost of increasing the test score, but -- just as crucially -- the

cost of ensuring that the right proctor (namely, one who would be

willing to facilitate the cheating) would both administer and then

access the exam materials themselves.                   It was that need that

underpinned the payment to Singer -- indeed, the indictment points

to the fact that the invoice that Singer's accountant emailed

McGlashan for the $50,000 explicitly said it was "[r]egarding [the

West Hollywood Testing Center][.]"             Had the "entire point" of the

                                      - 14 -
scheme been merely to increase his son's test scores, McGlashan

could have, for example, simply paid Singer to forge a score report

or even hack the ACT website to change the report.             Kelly, 140 S.

Ct. at 1573.       Such a plan might not have even required McGlashan's

son to take the exam.

           But McGlashan's plan proved much more intricate than

merely tampering with the scores.             Rather, the "entire point" of

the plan -- the "alternative strategy," as the indictment notes

McGlashan told "a counselor at his son's high school" -- was to

pay for a proctor to access the exam materials in order to change

McGlashan's son's test answers, which in turn would increase his

son's test score.          This scenario is easily distinguishable from

the traffic study in Kelly, which the Court explicitly noted was

"a cover story" meant to provide a pretext for the political

retribution behind the lane closures, or the extra toll collectors,

who one of the defendants "joked would just 'sit there and wait.'"

Kelly, 140 S. Ct. at 1574.           Here, by contrast, obtaining the ACT

exam in the manner Singer had devised was not pretextual, but

rather   was   a    core   service   for   which   McGlashan   paid   tens   of

thousands of dollars.          McGlashan was thus far from indifferent

toward obtaining the test itself; as alleged in the indictment,

doing so was not "some bit part in [the] scheme" at which he did

not aim.   Kelly, 140 S. Ct. at 1573; see also Gatto, 986 F.3d at

116 (noting in regards to a plan to conceal payments to college

                                     - 15 -
athletic recruits such that they would remain eligible to compete

that   "[u]nlike     in   Kelly,    where    there    was    a   sham    study   and

additional wages were paid only after the original plan was scaled

back due to safety concerns, here, depriving Universities of

athletic-based aid was at the center of the plan" (emphasis in

original) (citing Kelly, 140 S. Ct. at 1574)).                      We therefore

conclude that the indictment did adequately allege a scheme in

which the ACT exam was an object of the fraud.

                                        B.

            McGlashan     also     argues    that    the   indictment     does   not

allege a cognizable fiduciary relationship for purposes of the

honest services wire fraud element of Count Seven.                        But this

argument is barred by the conditional plea agreement to which

McGlashan   "knowingly,      voluntarily,       and    intelligently"      agreed.

United States v. Fernández-Santos, 856 F.3d 10, 14 (1st Cir. 2017).

            "While    plea   agreements        are    a    matter   of    criminal

jurisprudence, most courts, including this one, have held that

they are also subject to contract principles."                   United States v.

Vizcarrondo-Casanova, 763 F.3d 89, 102 (1st Cir. 2014) (quoting

United States v. Papaleo, 853 F.2d 16, 19 (1st Cir. 1988)).                       We

construe the plea agreement according to its plain language and

aim to "give effect to every term and phrase."                   United States v.

Alegría, 192 F.3d 179, 185 (1st Cir. 1999); see also United States

v. Davis, 923 F.3d 228, 235 (1st Cir. 2019) (interpreting a plea

                                      - 16 -
agreement's appellate waiver according to its plain language).

Nevertheless, we "construe ambiguities in favor of allowing the

appeal to proceed."        United States v. Morales-Arroyo, 854 F.3d

118, 120 (1st Cir. 2017).

            The   plea    agreement's   language   includes   a   careful

distinction between the preservation of factual and legal claims

on appeal.    As noted above, the agreement allowed McGlashan to

appeal the district court's denial of his motion to dismiss Count

Seven but expressly dictated that he could only make specified

arguments on appeal.       See supra at 7-8.   As is relevant here, the

preserved    honest      services-related    argument   was   that   "the

indictment did not adequately allege facts establishing that test

administrators owed a fiduciary duty to testing companies in this

case."   The agreement's use of the phrase "did not adequately

allege   facts"    mirrors    the    agreement's   language   concerning

McGlashan's right to advance an argument that "the indictment did

not adequately allege facts establishing a scheme to fraudulently

obtain standardized tests in this case."        Indeed, even though the

object of the fraud challenge was predicated on Kelly, the argument

that McGlashan advanced before us required an analysis of the

alleged facts of his scheme in order to assess the alleged role of

the ACT exam.     By contrast, the agreement's language preserving a

challenge based on the meaning of property as used in the wire

fraud statute allowed McGlashan to argue on appeal "that test

                                    - 17 -
scores cannot, as a matter of law, constitute property for the

purposes of the mail and wire fraud statutes."        And McGlashan

proceeded to make exactly that argument before us.         We would

therefore expect that McGlashan's honest services argument would

be akin to his object of the fraud claim; namely, an argument that

would primarily train on the facts set forth in the indictment and

would thus honor the agreement's express distinction between legal

and factual claims.     Cf. United States v. Okoye, 731 F.3d 46, 49

(1st Cir. 2013) (citing in the context of construing a waiver of

appeal provision to Smart v. Gillette Co. Long-Term Disability

Plan, 70 F.3d 173, 179 (1st Cir. 1995) ("Accepted canons of

construction   forbid     the   balkanization   of   contracts   for

interpretive purposes.")); United States v. Donath, 616 F.3d 80,

84 (1st Cir. 2010) ("When enforcing the appellate waiver, we stress

that both sides are obligated to live by the bargain they made.").3

     3  McGlashan argues in response to the government's claim of
waiver that the parties' "course of dealing" in their briefing to
the district court about the indictment's honest-services theory
indicates that, "read in light of the record, the plea agreement
preserved [his] challenge" related to the scope of § 1346 on
appeal. It is true that he, the government, and the district court
did discuss independent contractors, fiduciary duties, and those
concepts' application to § 1346 under Skilling v. United States,
561 U.S. 358 (2010), in various ways. But McGlashan overlooks the
fact that our court has repeated on a number of occasions that
"[i]f the language of an agreement 'unambiguously resolves an
issue, that usually ends the judicial inquiry,'" United States v.
Mejia, 55 F.4th 1, 7 (1st Cir. 2022) (quoting Alegría, 192 F.3d at
183), and -- consequently -- we typically "look[] outside the
document only as necessary to provide illuminating context or
resolve ambiguities in the writing," United States v. Marchena-

                                - 18 -
            Despite this limitation in the plea agreement, on appeal

about which fiduciary relationships the statute reaches, McGlashan

plainly asserts a legal argument.            He summarizes his argument in

the following manner:

            [T]he government's theory rests on an alleged
            informal fiduciary relationship between ACT
            and Dvorskiy, the test administrator, which
            supposedly arose from the totality of the
            circumstances     of    their     arm's-length
            contractual agreement.    Such relationships,
            however, are not cognizable under 18 U.S.C.
            § 1346, the honest services fraud statute,
            because they fall outside the "core pre-
            McNally applications" of the honest services
            doctrine that, per Skilling [v. United States,
            561 U.S. 358, 408 (2010)], define that
            statute's reach. The theory advanced by the
            government disregards these limits, creates
            uncertainty   in   all  manner   of   business
            relationships, and, if upheld, would violate
            due process.

It   is   true   that   McGlashan   does     perfunctorily   challenge   the

indictment's allegations that a fiduciary relationship existed

between    the   test   administrators     and   ACT,   characterizing   the

indictment's theory as "supposedly ar[ising] from the totality of

Silvestre, 802 F.3d 196, 202 (1st Cir. 2015). See also Alegría,
192 F.3d at 183 ("If, however, a plea agreement lacks clarity or
is manifestly incomplete, the need to disambiguate may justify
resort to supplementary evidence or other interpretive aids.").
As illustrated above, we find no ambiguity here that would warrant
resorting to extratextual evidence to construe the agreement. Cf.
United States v. Arroyo-Blas, 783 F.3d 361, 365 (1st Cir. 2015)
("[A]s in contract law, we will not 'conjur[e] up an ambiguity [in
a plea agreement] where none legitimately exists.'" (second and
third alterations in original) (quoting United States v. Anderson,
921 F.2d 335, 338 (1st Cir. 1990))).       His course of dealing
argument is therefore unavailing.

                                    - 19 -
the circumstances of their arm's length contractual agreement" and

"allegedly ar[ising] circumstantially from the parties' course of

dealing, rather than inhering in their formal legal roles."                   But

that is also where his fact-based argument ends: the honest

services section of his appeal brief mentions "Dvorskiy" and "ACT"

only twice each after the summary excerpted above (either by name

or by reference), and only spends three sentences discussing the

facts of McGlashan's case over the course of ten pages.                       This

presentation of his argument does not invite us to consider whether

the indictment adequately alleged facts that establish a fiduciary

relationship between the test administrators and ACT.                    To the

extent that McGlashan has made a factual argument, "[w]e long have

warned   that   'issues     adverted    to     in   a    perfunctory     manner,

unaccompanied   by   some   effort     at    developed       argumentation,   are

deemed waived.'   The skeletal presentation of this argument in the

defendant's brief 'leav[es] the court to do counsel's work' -- and

that is not our proper province."           United States v. Gonzalez, 981

F.3d 11, 23 (1st Cir. 2020) (second                 alteration in original)

(quoting United States v. Zannino, 895 F.2d 1, 17 (1st Cir. 1990)).

          Rather,    McGlashan's       argument         is    premised   on   his

objection to the application of § 1346 to informal fiduciary

relationships writ large.         This is       further evidenced by the

position that McGlashan urges us to take in the conclusion of the

honest services section of his brief: he calls for us to "construe

                                  - 20 -
the statute to reach only formal fiduciary relationships, in line

with the core pre-McNally applications." Even with his perfunctory

statements about Dvorskiy's relationship with ACT, we fail to

comprehend how the argument focuses on whether the indictment

adequately alleged facts establishing the test administrators'

fiduciary duties to ACT.   It is instead a legal argument about the

scope of § 1346, pure and simple.   As noted above, the language of

the plea agreement plainly does not allow for legal challenges to

the honest services theory included in Count Seven.      McGlashan

therefore waived this argument when he entered the conditional

guilty plea agreement.

          Affirmed.

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