Court Opinion

ID: 4310349
Source: CourtListenerOpinion
Date Created: 2018-09-06 21:00:13.135811+00
Date Added: 2024-06-11T14:43:45.098238
License: Public Domain

United States Court of Appeals
                     For the First Circuit

No. 17-2092

                    UNITED STATES OF AMERICA,

                            Appellee,

                               v.

                       ANTONIO M. FREITAS,

                      Defendant, Appellant.

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

          [Hon. William G. Young, U.S. District Judge]

                             Before

                Torruella, Thompson, and Barron,
                         Circuit Judges.

     Phillip N. Beauregard, with whom Law Offices of Beauregard,
Burke & Franco was on brief, for appellant.
     Mark T. Quinlivan, Assistant United States Attorney, with
whom Andrew E. Lelling, United States Attorney, was on brief, for
appellee.

                        September 6, 2018
          THOMPSON, Circuit Judge.

                             PREFACE

          Antonio Freitas stands convicted of bulk-cash smuggling

and currency structuring, in violation of 31 U.S.C. §§ 5332(a) and

5324(c).1 Freitas believes we must vacate his convictions because,

according to him, the district judge quadruply erred — first by

admitting certain statements under the coconspirator exception to

     1 Subpart (a)(1) of section 5332(a), the bulk-cash-smuggling
statute, punishes anyone who,
     with the intent to evade a currency reporting
     requirement under section 5316, knowingly conceals more
     than $10,000 in currency or other monetary instruments
     on the person of such individual or in any conveyance,
     article of luggage, merchandise, or other container, and
     transports or transfers or attempts to transport or
     transfer such currency or monetary instruments from a
     place within the United States to a place outside of the
     United States . . . .
The cross-referenced provision, 31 U.S.C. § 5316, generally
requires that "a person or an agent or bailee of the person . . .
file a report . . . when [he] knowingly . . . transports, is about
to transport, or has transported, monetary instruments" over
"$10,000 at one time . . . from a place in the United States to or
through a place outside the United States" (the statute's
description of the required report is irrelevant for our purposes).
And subpart (a)(2) of the bulk-cash-smuggling statute makes clear
that "concealment of currency on the person of any individual
includes concealment in any article of clothing worn by the
individual or in any luggage, backpack, or other container worn or
carried by such individual."
     Section 5324(c), the currency-structuring statute, prohibits
a person from "structur[ing] . . . any importation or exportation
of monetary instruments" for the purpose of "evading" section
5316's reporting requirements. Section 5324(c) covers those who
"structure or assist in structuring, or attempt to structure or
assist in structuring."
                              - 2 -
the hearsay rule; next by instructing the jury that the government

can   prove    the   concealment     element    of    the   bulk-cash-smuggling

charge   through     evidence   of    structuring,       an   instruction    that

wrongly removed the mental-state element from both crimes; then by

not granting his motion for acquittal on the structuring count;

and finally by not adequately responding to the government's

prejudicial     comments   in   closing       argument      and   at   sentencing.

Disagreeing, we affirm.

                           HOW THE CASE GOT HERE

              Presented in the light most favorable to the jury's

verdict, see United States v. Rodríguez–Soler, 773 F.3d 289, 290

(1st Cir. 2014), the underlying facts are easily summarized.

                         Smelling Something Fishy

              In May 2015, an IRS agent posing as a financial agent

named "Bob" cold-called Carlos Rafael.           Nicknamed "the Codfather,"

Rafael then owned Carlos Seafood, a commercial-fishing business

located in New Bedford, Massachusetts.               "Bob" told Rafael that he

and a man named "Lenny" — actually an undercover agent as well —

wanted to buy Carlos Seafood.          His interest piqued, Rafael agreed

to meet with "Bob" and "Lenny" to discuss a possible sale.

              Two times the next month, in June 2015, "Bob" and "Lenny"

— wearing concealed body wires — met with Rafael at Carlos Seafood.

Rafael told them that he might be willing to part with the business

                                      - 3 -
if they could come up with $150 million or so.               He also bragged

that he had fish sales that were not being taxed properly and that

he avoided paying income tax on piles of cash he was getting from

sales to a New York customer.

              After summering in Portugal, Rafael told the agents in

a   secretly-recorded    meeting     in    October   2015    that      he   had   a

Portuguese friend named "Freitas" who worked for the "Sheriff's

Department" and could sneak cash by security at Boston's Logan

International Airport ("Logan").          Given the importance of what he

said    there,   we   quote   from   the     transcript     of   the    recorded

conversation at length (fyi, Rafael is identified in the transcript

by his first name, Carlos):

       CARLOS:   But I guess in Boston, I can get the money
       through. I have one of the guys in Boston, one of those
       fuckin' agents who is my friend, and I give him the money
       before I go through security.

       LENNY:    OK, and then he . . .

       CARLOS:    Then I go to the bathroom.

       LENNY:    And he gives you the money.

       CARLOS:    He gives me the motherfucking money.

       BOB:   Nice.

       CARLOS: Even if he is not in the airport, he lives in
       Rhode Island, I'll call him up.    I don't give him
       nothing. He is my friend.

       LENNY:    Oh he's your friend.

                                     - 4 -
     CARLOS:   I call him.    I says, Hey, I'm flying out
     tonight. "You're not fucking, I'm not working tonight."
     No, you better get your fucking ass here because I got
     like 60,000 in my fucking ass. I ain't going through
     the fucking thing.   So he goes there, I give him the
     envelopes, he puts them in his pockets. He doesn't go
     through security because he has one of those fuckin'
     badges. He's an agent over there.

The transcript continues:

     CARLOS:    He's been over to my house, we're buddies.

     BOB:   Heck yeah he's your buddy I'd make him my buddy
     too.   That's a good buddy to have.

     CARLOS:    He's a Portagee.

     BOB:   Oh, he's Portuguese?     Even better.

     CARLOS:    He's from St. Michael, he's from the Azores.

     BOB:   He's from there.

     [crosstalk]

     LENNY:    You realize he works for the . . .

     BOB: He works for the Sheriff's Department[.] Oh sweet.

     CARLOS: I got him the job, I got him the raises, so
     he'll do what the fuck I tell him to do. He called me.
     He says, "what the fuck is going on, everybody got a
     promotion in this fuckin' place but me." So I'm like
     this with the sheriff. I called the Sheriff and I said
     ["]what the fuck are you doing to me Tom? Fuckin Freitas
     has been there for so many fuckin' years, you're not
     going to give him a fuckin' promotion and a raise?"
     "Jesus Carlos, we do not have enough money in the
     budget." I said fuck off, find a way, give the kid a
     raise. He got his promotion, right, so he called me and
     said I want to thank you very much, I finally got my
     fuckin' promotion and my raise. So it's nice to know
     people.

                                   - 5 -
Rafael     explained   that      Freitas    worked   on     customs   with   the

immigration unit of the Sheriff's Department.                And he said that

Freitas could also help them get their cash out of the country by

bypassing airport security.

            A few days later, still in October 2015, "Bob" asked

Rafael over the phone if Rafael could help him and "Lenny" get

their money around airport security so that they could take it to

Portugal.     All right, Rafael said.            During another phone call,

also in October 2015, "Bob" asked Rafael if Freitas could help get

the money through the airport.             Rafael said yes, but added that

"Bob" could not meet Freitas in person.                   This is what Rafael

proposed:     "Bob" would give the money to Rafael.              Rafael would

hand the money to Freitas.          Freitas would get the money through

security and give the money to back to Rafael.                And Rafael would

deliver the money back to "Bob."

                            Fishing for Freitas

            Checking some databases, agents then found an Antonio

Freitas,    an   employee   of    the    Bristol   County    Sheriff's   Office

assigned since 2007 as a task-force officer with U.S. Immigration

and   Customs    Enforcement     ("ICE")    in   Boston.      Freitas,   agents

learned, had a security badge for Logan that let him bypass

security.    And Freitas's employment file showed that in September

                                        - 6 -
2014,     he    got     promoted      to    the    position    of    "Sergeant     ICE

Investigations."

               Agents    also    learned     that    around    the    time   of    his

promotion, Freitas completed a multiday training program for ICE

officers       that   covered    (among     other    topics)   financial     crimes,

including structuring and bulk-cash smuggling — an instructor, for

example, told attendees that structuring involved "having more

than $10,000 in cash and breaking it into smaller amounts to

conduct financial transactions in order to avoid the reporting

requirements." At the end of the training, Freitas took and passed

a multiple-choice exam, getting every question right — including

correctly answering that air passengers leaving the United States

must report the "transportation of currency in excess of $10,000"

on them "or in their luggage."

                                  Catching Freitas

               At some point in 2016, Rafael asked Freitas to courier

$20,000 from the United States to Portugal and deposit the funds

into Rafael's bank account there.                   Freitas felt uncomfortable

taking that much cash because he knew he would have to file a

disclosure form.         But he took $17,500 from Rafael and divided it

between    himself      and     his   girlfriend,     Giovania      Lima   (whom   the

government called to testify at trial). With something like $8,500

or $9,000 in his bag and the rest in hers, Freitas and Lima passed

                                           - 7 -
through Logan's security one evening in early February 2016 and

jetted off to Portugal (agents surveilling the scene saw them board

without incident).     Once there, Freitas made the required deposit

for Rafael.    Bank records confirm that deposit.       And phone records

reveal that Freitas and Rafael exchanged multiple calls right

before the Portugal getaway. Lima would later say that just before

the trip, Freitas told her that he had to take a friend's money to

Portugal.     Freitas got her travel bags together, she said.           And

looking at her bags, she saw an envelope with $4,000 or $9,000

scrawled across it.      She understood that she had to carry that

envelope with her on the flight and that Freitas would carry a

second envelope with him — which is precisely what they did.           And

while in Portugal, Lima added, Freitas deposited "about $17,000"

into a bank account.

            Coinciding with the arrest of Rafael, law-enforcement

agents confronted Freitas at the end of February.             Among other

things, agents asked him if Rafael ever asked him to carry money

out of the country or circumvent airport screening.                 Freitas

admitted taking money to Portugal for him earlier that month,

saying at one point that he took $8,500 and at other points that

he took $9,000.      Agents also a played piece of the recording of

the October 2015 meeting involving Rafael, "Bob," and "Lenny" (we

block-quoted    a   snippet   of   the   recording's   transcript   above).

                                    - 8 -
Listening to the audio, Freitas's face became flush.                   He then

admitted that he had carried money for Rafael in the past because

Rafael had helped him get a promotion and had co-signed a home-

improvement loan for him.

           All   this,    and   more,    led   to     Freitas's    arrest    and

indictment on (as relevant here) bulk-cash-smuggling and currency-

structuring   charges.      Agents      arrested     Rafael     too.   Waiving

indictment,   Rafael     pled   guilty    to   a    raft   of   charges     in   a

superseding information, including conspiracy, false labeling of

fish, bulk-cash smuggling, tax evasion, and falsifying federal

records.   But Freitas rolled the dice and went to trial.

           The government's witnesses testified consistent with the

facts described above. Freitas's attorney called only one witness,

Bristol County Sheriff Thomas Hodgson.             Hodgson testified that he

knew Rafael from the community, though he did not consider him a

friend.    Hodgson added that Freitas's becoming a "Sergeant ICE

Investigations" was "not a promotion per se" but a change in status

to a "designated rank" for a "specialty position."              And as for how

the change happened, Hodgson remembered Rafael's saying over the

phone that he needed a promotion.              But Rafael's call did not

influence his decision, Hodgson stressed.

           Freitas's counsel tried responding to the government's

case through his closing argument.         For example, counsel insisted

                                   - 9 -
that Freitas could not be guilty of bulk-cash smuggling because

the   government   failed    to   prove    that    he   intended   to   evade   a

currency-reporting requirement.           And "if there's no smuggling of

money," he stressed, "then there is no structuring in this case"

either.      What Freitas "did was not illegal," counsel protested,

because "[h]e did nothing but carry less than $10,000 himself

outside the United States."

             Rejecting Freitas's defense, the jury found him guilty

on    both   counts.   The   district      judge    then   sentenced    him     to

concurrent terms of a year and a day in prison, plus three years

of supervised release.       And as we said, he now appeals, raising

four claims of error.        Taking them up in the order he presents

them — and adding additional details as needed as we move along —

we see no reason to reverse.2

                       HEARSAY-STATEMENTS CLAIM

             Freitas's lead argument is that the judge slipped by

admitting Rafael's recorded statements under the coconspirator

exception to the hearsay rule.            See Fed. R. Evid. 801(d)(2)(E)

       2
       Freitas, by the way, makes no argument that his bulk-cash-
smuggling and currency-structuring convictions infracted the
Double Jeopardy Clause of the Fifth Amendment.      Cf. generally
United States v. Del Toro-Barboza, 673 F.3d 1136, 1148-49 (9th
Cir. 2012) (explaining why the Ninth Circuit believed the
defendants'   convictions  under   the   bulk-cash-smuggling  and
currency-structuring statutes did not violate the Double Jeopardy
Clause). So we say nothing on that score.
                                   - 10 -
(explaining that a statement is not hearsay if it is offered

against          the      defendant    and   "was     made     by   [the      defendant's]

coconspirator during and in furtherance of the conspiracy").3                          As

he sees things, "[t]he broad fishing conspiracy" Rafael bragged

about       to      the    undercover    agents       back    in    October    2015   "was

fundamentally different and broader in scheme" than the acts that

formed the basis of his conviction.                          Continuing, he says the

government "failed to produce any evidence linking" his February

2016        trip     "to    Portugal    with    Rafael's       broad   [October]      2015

statements about his past practice."                    And "[t]he unholy effect of

blending two distinct conspiracy scenarios — Rafael's version in

October 2015 vis-à-vis Freitas's actions in February 2016" —

amounts to reversible error, or so he contends.

                   For its part, the government asserts that the judge could

reasonably conclude from the evidence that a conspiracy existed in

        3
       Here is how this exception works. If a defendant challenges
the admissibility of a supposed coconspirator statement, the judge
can conditionally admit the evidence and delay ruling until the
close of all the evidence. See, e.g., United States v. Correa-
Osorio, 784 F.3d 11, 23-24 (1st Cir. 2015) (citing, among other
cases, United States v. Petrozziello, 548 F.2d 20 (1st Cir. 1977)).
The government "must then prove by a preponderance of the evidence
(apart   from   the   statements   themselves)  the   elements   of
admissibility under the exception — that the defendant and the
speaker were coconspirators and that the speaker made the statement
during the course and in furtherance of the conspiracy." Id. at
24.   And if the government falls short, the defendant can then
move "the judge to declare a mistrial or strike the statement[]."
Id.
                                             - 11 -
which Freitas would help Rafael hide money from the IRS by helping

him smuggle cash to Portugal.         The government also believes that

the judge could rationally find that Rafael made the complained-

about statements in furtherance of the conspiracy because they

described the conspiracy's modus operandi and instilled confidence

in the prospective buyers that they could use Freitas's services

if they bought Carlos Seafood.        Also, according to the government,

the fact that Freitas's conduct in February 2016 (e.g., flying

with his girlfriend) differed from the conduct Rafael described in

October 2015 (e.g., flashing a badge to get through security) did

not strip the conspiracy of its essential purpose — i.e., helping

Rafael smuggle cash out of the United States to Portugal so that

Rafael could avoid paying income taxes.

           Both sides agree that because Freitas did not raise these

points below, he must run the gauntlet of plain-error review — a

grueling assignment, for sure, requiring him to "show (1) error,

(2)   plainness,   (3)   prejudice,    and   (4)   an   outcome   that   is   a

miscarriage of justice or akin to it."              See United States v.

Edelkind, 467 F.3d 791, 797 (1st Cir. 2006); see also United States

v. Gordon, 875 F.3d 26, 30 (1st Cir. 2017) (stressing that "[t]he

party asserting that an error was plain must carry the burden of

establishing that the claimed error satisfies each element of this

standard").   But this he cannot do.         Here is why:

                                 - 12 -
            Agents testified that Freitas admitted that (a) Rafael

gave him $17,500 to take on the Portugal flight; that (b) he split

the $17,500 into increments just under $10,000; that (c) he and

Lima carried those sums in their separate bags on the flight; and

that (d) he deposited the $17,500 into Rafael's bank account in

Portugal.    On top of that, Lima testified that (e) Freitas gave

her an envelope with $4,000 or $9,000 written on it to take in her

bag to Portugal while he took a separate envelope with him there

too; that (f) neither he nor she disclosed that they had just under

$10,000 with them on the flight; and that (g) after landing in

Portugal, Freitas deposited the money in a bank.           Another agent

testified that (h) Freitas participated in a training program that

discussed    financial   infractions,    including   the    elements   of

structuring and bulk-cash smuggling, and that (i) he correctly

answered a test question that a person leaving the United States

must report the "transportation of currency in excess of $10,000"

on them "or in their luggage."

            So even assuming (without deciding) that Freitas can

satisfy plain error's error and plainness elements, he cannot

satisfy the prejudice element.      Cf. generally United States v.

Turbides-Leonardo, 468 F.3d 34, 39 (1st Cir. 2006) (concluding

there that "regardless of how we resolve the first two elements,

the appellant stumbles over the third").       The prejudice analysis

                                - 13 -
here turns on whether it is reasonably probable that the result

below would have been different without the challenged statements,

see United States v. Bramley, 847 F.3d 1, 7 (1st Cir. 2017) — the

statements' prejudicial effect, in other words, must have been

"'substantial and injurious,'" see Turbides-Leonardo, 468 F.3d at

39 (quoting United States v. Dominguez Benitez, 542 U.S. 74, 81

(2004)); see also Rosales-Mireles v. United States, 138 S. Ct.
1897, 1904-05 (2018).   Freitas's burden is far from easy.    See

Dominguez Benitez, 542 U.S. at 82 (declaring that the plain-error

"standard should . . . encourage timely objections and reduce

wasteful reversals by demanding strenuous exertion to get relief

for unpreserved error").   And given the avalanche of compelling

evidence mentioned in points (a) through (i) above — which showed

that Freitas knew the law, that he knowingly evaded the law's

requirements, and that he ended up helping Rafael sneak over

$10,000 out of the country for deposit in a foreign bank — we

simply cannot conclude that Freitas bore his burden of showing

that it is reasonably probable that the admission of Rafael's

statements affected his verdict.

          Trying to persuade us otherwise, Freitas speculates

"that the jury found [him] guilty by association (with Rafael)

rather than guilty by his own actions."       Perhaps.    But his

conjecture cannot help a him carry his burden on the third element

                             - 14 -
of the plain-error test.   Bramley, 847 F.3d at 8 (discussing Jones

v. United States, 527 U.S. 373, 394-95 (1999)).       So Freitas's

guilt-by-association surmise is not a game-changer for him.

          On then to his second claim.

                    INSTRUCTIONAL-ERROR CLAIM

          As noted in footnote 1, the bulk-cash smuggling statute

— section 5332 — applies to "[w]hoever, with the intent to evade"

certain currency-reporting requirements under section 5316,

     knowingly conceals more than $10,000 in currency or
     other monetary instruments on the person of such
     individual or in any conveyance, article of luggage,
     merchandise, or other container, and transports or
     transfers or attempts to transport or transfer such
     currency or monetary instruments from a place within the
     United States to a place outside of the United States
     . . . .

31 U.S.C. § 5332(a)(1) (emphasis added).     And subpart (a)(2) of

that provision says that "concealment of currency on the person of

any individual includes concealment in any article of clothing

worn by the individual or in any luggage, backpack, or other

container worn or carried by such individual."

          At the charge conference, the judge indicated that he

would instruct the jury on the elements of aiding and abetting

bulk-cash smuggling.   The government saw no need for an aiding-

and-abetting instruction because (according to the government)

Freitas "himself" engaged in bulk-cash smuggling, with his money

                               - 15 -
structuring satisfying the concealment element of the crime.    "All

right," said the judge, "I'll charge it that way."

          And the judge did so, telling the jury that on the

concealment element, the government had to prove

     that Mr. Freitas knowingly concealed the transport of
     more than $10,000.    Now that first thing is knowing
     concealment.   People don't commit crimes by making
     mistakes or by just being negligent, you've got to know
     that you've got a duty to make a report, or at least
     you've got to — you're not allowed to move more than
     $10,000 cash money into or out of the country.      And
     "conceal" — "conceal" is everything that the natural
     mind would think of as "concealing," it means hiding it
     and the like, but it also means structuring, the second
     crime.

The judge added:

     To "structure," a way of concealing, because of course
     its money, is if you've got more than one person
     traveling, it is to break it up, just divide it up so
     that each person is carrying less than $10,000, that
     counts as "concealing." So the first thing on the "bulk-
     cash smuggling" is knowingly to conceal a sum of money
     more than 10,000 — cash money now, more than $10,000.

Bulk-cash smuggling, continued the judge,

     can be accomplished in different ways, the structuring
     here — Congress wisely — Congress understood that when
     they were talking about money and they were putting an
     amount of $10,000 on it, that, . . . money is divisible
     into smaller amounts of money, and so they made another
     crime and that's the crime of "structuring."

And "each charge," the judge stressed,

     has to prove something that the other one doesn't, so
     for "structuring," it's not taking the money and hiding
     it somewhere, that would be to conceal it — like in the
     false bottom of a carry-on, that would be to conceal it
     knowingly, but you can "conceal" by dividing it up, if
                             - 16 -
        you've got more than one person traveling, so that each
        person has less than $10,000.    But then if you do it
        that way, then you've also committed the crime of
        structuring.

Freitas's lawyer timely objected to the instruction, arguing that

the    judge    wrongly       told    "the    jury   that     'concealment'     can    be

'structuring.'"         But the judge overruled the objection, commenting

that    "the    law     is    clear    that    'structuring'         can   satisfy    the

concealment element."

               Before    us,    Freitas       attacks   the    instruction      on    two

fronts.     He first insists the judge incorrectly instructed the

jury that the concealment element of bulk-cash smuggling includes

structuring.      He then insists the instruction removed the mental-

state (or "mens rea") element from both bulk-cash smuggling and

currency-structuring crimes.              Neither foray succeeds, however.

               As for the proper standard of review, for preserved

claims of instructional error we apply de novo review to "questions

about    'whether       the    instructions      conveyed      the    essence   of    the

applicable law'" and abuse-of-discretion review to "questions

about 'whether the [judge's] choice of language was unfairly

prejudicial.'"        United States v. Sabean, 885 F.3d 27, 44 (1st Cir.

2018) (quoting United States v. Sasso, 695 F.3d 25, 29 (1st Cir.

2012)).     Of course, we review unpreserved claims only for plain

error.     See, e.g., United States v. Deppe, 509 F.3d 54, 58 (1st

Cir. 2007).
                                         - 17 -
          Repeating what did not work below, Freitas initially

faults the judge for instructing the jury that proof of structuring

can satisfy the concealment element of the bulk-cash-smuggling

statute — in his telling, that instruction "had no basis in either

the words of the statute, or in case law."       Noting that Congress

did not define "conceals" in the bulk-cash-smuggling statute, and

that no opinion interprets that term, the government responds that

the common meaning of "'conceals' is to hide or keep it from

notice, and structuring — which," the government is quick to point

out, "is defined as breaking up a single transaction above a

reporting threshold into two or more separate transactions" to

"evad[e] a financial reporting requirement — fits comfortably

within that ordinary meaning."      Because Freitas preserved this

claim, and the claim involves the judge's interpretation of the

concealment element, our review is de novo.

          Freitas's   lead   argument   —   again,   that   the   judge's

instruction improperly conveyed that the government can prove the

concealment element with structuring evidence — stumbles out of

the gate, because he fails to develop it sufficiently here and so

has waived it.   Bear with us as we explain.

          Freitas briefly raises this issue first by saying that

the reporting-offense statute (31 U.S.C. § 5316, which is cross-

referenced in the bulk-cash-smuggling act) "imposes the reporting

                               - 18 -
requirement" only "on a singular person who is prohibited from

transporting currency to a foreign country in excess of $10,000

without filing the requisite form," and that he did not personally

transport more than $10,000 to Portugal.4   Then he strays into a

mens-rea discussion (more on that in a moment).   And then he gets

to the crux of his argument, complaining that the instruction had

no support "in either the words of the statute, or in case law."

But this appears in a single sentence, is not seriously supported

(he, for example, neither cites any precedent nor explains the

lack of precedent, assuming he found none), and is therefore

waived.   See United States v. Zannino, 895 F.2d 1, 17 (1st Cir.

1990) (repeating "the settled appellate rule that issues adverted

to in a perfunctory manner, unaccompanied by some effort at

developed argumentation, are deemed waived"); see also Rodríguez

v. Mun'y of San Juan, 659 F.3d 168, 175-76 (1st Cir. 2011) (same).

          Having done little to elaborate on his argument in his

initial brief, Freitas attempts a text-based argument in his reply

brief that keys on the bulk-cash-smuggling statute (31 U.S.C.

     4 As mentioned in our first footnote, section 5316 basically
requires that "a person or an agent or bailee of the person . . .
file a report . . . when the person, agent, or bailee knowingly
. . . transports, is about to transport, or has transported,
monetary instruments" over "$10,000 at one time . . . from a place
in the United States to or through a place outside the United
States."
                             - 19 -
§ 5332(a)), rather than the reporting-offense statute (31 U.S.C.

§ 5316).   Quoting subpart (a)(1) of section 5332, he asserts that

the bulk-cash-smuggling statute speaks in terms of an "individual"

carrying over $10,000 "on the person of such individual or in any

conveyance, article of luggage, merchandise, or other container."5

He then notes that neither he nor Lima carried over $10,000 — "two

separate persons" carried "the sub 10K amounts."         "For this

reason," he writes, the judge reversibly "erred by instructing the

jury that the concealment element of the bulk cash smuggling

statute could be proven by structuring alone, i.e. the otherwise

innocent act of dividing $17,500 into two sub $10K sums."

     5 For the reader's convenience, we repeat section 5332's
pertinent language here, with italics added:
     (a) Criminal offense.—
         (1) In general.— Whoever, with the intent to evade a
         currency reporting requirement under section 5316,
         knowingly conceals more than $10,000 in currency or
         other monetary instruments on the person of such
         individual or in any conveyance, article of luggage,
         merchandise, or other container, and transports or
         transfers or attempts to transport or transfer such
         currency or monetary instruments from a place within
         the United States to a place outside of the United
         States, or from a place outside the United States to
         a place within the United States, shall be guilty of
         a currency smuggling offense . . . .
         (2) Concealment on person.—    For purposes of this
         section, the concealment of currency on the person of
         any individual includes concealment in any article of
         clothing worn by the individual or in any luggage,
         backpack, or other container worn or carried by such
         individual.
                               - 20 -
          Conspicuously absent from Freitas's argument is any

discussion of whether or how section 5332's subpart (a)(2) applies

here.   Curious, we raised the topic at oral argument this way.

Subpart (a)(1), we noted, is structured in two pieces separated by

the word "or."   The first piece focuses on currency concealed "on

the person of such individual" — a phrase subpart (a)(2) defines

as "includ[ing] concealment in any article of clothing worn by the

individual or in any luggage, backpack, or other container worn or

carried by such individual."     And after talking about currency

concealed "on the person of such individual," subpart (a)(1)'s

second piece — following the "or" — focuses on currency concealed

"in any conveyance, article of luggage, merchandise, or other

container," with the "or" suggesting there is a difference between

what comes before it and what comes after it. Cf. generally United

States v. Woods, 571 U.S. 31, 45-56 (2013) (recognizing that while

the connection of terms "by the conjunction 'or' . . . can

sometimes introduce an appositive — a word or phrase that is

synonymous with what precedes it (Vienna or Wien, Batman or the

Caped Crusader) — its ordinary use is almost always disjunctive,

that is, the words it connects are to be given separate meanings"

(internal quotation marks omitted)).    Given how subpart (a)(1)'s

"on the person" piece is specifically defined in subpart (a)(2) to

include "such individual['s] "clothing . . . or . . . luggage," we

                               - 21 -
wondered whether subpart (a)(1)'s "in any conveyance, article of

luggage," etc., piece — the piece that follows the "or" — refers

to another person's luggage, merchandise, and so on.        No, thought

Freitas; yes, thought the government.

          As interesting as this issue is, however, we need not

decide who is right here.    You see, as a general rule, one cannot

use a reply brief to develop an argument cursorily made in an

opening brief.   See, e.g., Small Justice LLC v. Xcentric Ventures

LLC, 873 F.3d 313, 323 n.11 (1st Cir. 2017); Pignons S.A. de

Mecanique v. Polaroid Corp., 701 F.2d 1, 3 (1st Cir. 1983).            That

is because an argument raised for the first time in a reply brief

"come[s] too late to be preserved on appeal."              Id. (quoting

parenthetically Braintree Labs., Inc. v. Citigroup Glob. Mkts.

Inc., 622 F.3d 36, 44 (1st Cir. 2010)).          And Freitas offers no

reason for ignoring the general rule.          So this is an issue for

another day, when it is properly preserved and fully developed.

          Turning then to Freitas's mental-state argument, we

repeat that he believes the offending instruction erased the mens-

rea element from both crimes of conviction, bulk-cash smuggling

and   currency   structuring.      In    his    telling,   by   equating

"structuring"    with   "concealment,"   the    "instruction    left     no

possibility for the jury to conclude that [he] lacked a requisite

intent to evade" the reporting requirement.        Having débuted this

                                - 22 -
theory here (he gives us no indication at all that he preserved it

below), Freitas can win only if he shows plain error.   But we find

no error — much less a plain error — for a simple reason:   Freitas

ignores that the judge gave the supposedly wrong instruction in

the context of discussing whether structuring can suffice for

concealment for purposes of bulk-cash smuggling.    And he ignores

as well that for both crimes of conviction, the judge also told

the jury that it needed to find that he acted with the intent to

evade the reporting requirement.    Viewing the instructions as a

whole — as we must, see, e.g., United States v. Candelario–Santana,

834 F.3d 8, 27 (1st Cir. 2016) — we easily conclude that Freitas's

complaint that the judge scrapped the mental-state element is

simply wrong.

          Freitas also suggests in the instructional section of

his brief that he lacked the necessary mental state for structuring

because he "knew that it was unlawful for him to carry and hide or

conceal on his person or luggage $10,000 or more from the United

States" and so he "set out to act in accordance with the law."   To

the extent this argument targets the judge's instruction — as

opposed to the evidence's sufficiency, which we discuss in the

next part of this opinion — it goes nowhere (whether preserved or

not).   By his argument's own terms, Freitas knew he could not

conceal more than $10,000, which left him with two options: comply

                              - 23 -
with   section   5316's   requirements     and   lawfully   report    it,   or

structure the possession of the funds so he did not have to report

it. Put simply then, his own brief shows he acted with the required

intent of avoiding the reporting requirements.           And that is that

on the instruction claim.

                      INSUFFICIENT-EVIDENCE CLAIM

           As we just intimated, Freitas's mental-state argument

also has the flavor of a sufficiency challenge:                he seems to

suggest that the judge should have granted him a judgment of

acquittal on the section-5324 currency-structuring charge, his

theory being that the government failed to prove that he had the

requisite mental state to evade a reporting requirement.                    To

repeat, Freitas concedes that he "knew that it [was] unlawful for

him to carry and hide or conceal on his person or luggage" more

than $10,000 "from the United States, into a foreign country" —

remember, section 5316's reporting requirements (cross-referenced

in the currency-structuring statute) only apply to those carrying

over $10,000.     And because he did not carry over $10,000 in his

luggage,   he    thinks   that   he   cannot     be   guilty   of    currency

structuring.     He also insists — without offering any authority (or

explaining the absence of authority) — that his structuring was

actually an attempt to "comply" with the section 5316 limit and

thus he cannot be criminally liable.           The government's principal

                                  - 24 -
response is that structuring to "comply" with the section 5316

limit — where "compliance" involves diluting funds to avoid the

$10,000   threshold   —   is    exactly     the   conduct      the   currency-

structuring statute targets.        And, the government adds, a jury

could reasonably conclude from the evidence that Freitas divided

the $17,500 that Rafael had given him into two sub $10,000 sums to

evade the reporting requirement.        For our part, we think Freitas's

claim is a nonstarter.

          Freitas made a general acquittal motion at the close of

the government's case.         But he did not renew the motion after

presenting evidence in his defense or in a timely post-verdict

motion.   See Fed. R. Crim. P. 29(c)(1).            So after viewing the

evidence in the light most favorable to the prosecution, he must

convince us that affirming the verdict will work a "clear and gross

injustice."   See, e.g., United States v. Ponzo, 853 F.3d 558, 580-

81 (1st Cir. 2017); United States v. Cruzado-Laureano, 404 F.3d
470, 480 (1st Cir. 2005).       That is a tall order for any defendant,

since the clear-and-gross-injustice standard is "a particularly

exacting variant of plain error review."            See United States v.

Foley, 783 F.3d 7, 12-13 (1st Cir. 2015) (emphasis added).

          But   Freitas   does    not   attempt    to   bear    this   burden.

Putting aside that he wrongly sketches the evidence in the light

most favorable to him rather than to the government, Freitas fails

                                   - 25 -
to even mention the clear-and-gross-injustice standard — much less

develop any argument showing why and how it is met.    And because

it is not our job to make arguments that an appellant has not made

for himself, we consider his sufficiency claim waived.           See

Zannino, 895 F.2d at 17; see also Rodríguez, 659 F.3d at 175-76.

                    PREJUDICAL-COMMENTS CLAIM

          This leaves Freitas's last set of arguments, alleging

that the prosecutor made prejudicial comments in his closing and

at sentencing — arguments we easily turn aside.

                                Closing

          During closing argument, the prosecutor highlighted for

the jury Rafael's recorded statements that Freitas helped him get

cash around airport security.    Here is what the prosecutor said:

          Then it's Rafael's turn to ask Freitas for
     something, and again you can refer to the transcript
     . . . .    This is what Carlos gets.    "But I guess in
     Boston I can get the money through, I have one of the
     guys in Boston, one of those fucking agents who's my
     friend, I give him the money before I go through
     security." And he goes on to discuss in detail about
     how he gives the cash to Tony Freitas beforehand. Mr.
     Freitas, using his security badge, goes around security,
     circumvents security, goes to the secure areas of the
     airport, meets Mr. Rafael at the other side, in the men's
     room, gives the money back to Rafael, and Rafael gets on
     the plane.

          Freitas's lawyer objected immediately.     In overruling

it, the judge told the jurors that the government could refer to

evidence admitted at trial and reminded them that the conduct that

                                - 26 -
Rafael described in the recorded conversations was not the conduct

"that was charged here."

               Because   Freitas's     attorney     timely   objected      to   the

prosecutor's comment, we ordinarily would review this claim de

novo to see whether the contested comment was improper — and if

yes, whether it was harmful, knowing that the harmfulness question

turns on whether the comment "so poisoned the well that the trial's

outcome was likely affected, thus warranting a new trial."                 United

States v. Rodriguez, 675 F.3d 48, 62 (1st Cir. 2012) (internal

quotation marks omitted); see also United States v. González-

Pérez, 778 F.3d 3, 19 (1st Cir. 2015).                  But there is a serious

hitch    for    Freitas:     Under     an    argument    heading    accusing    the

government of injecting "unfairness and prejudice . . . into the

trial and sentencing," Freitas's main brief implies that the

prosecutor's       closing   to   the       jury   improperly      "repeated    the

allegation that Freitas and Rafael were co-conspirators."                  But as

the government notes, outside of this single sentence — tacked

onto the end of his brief, as a seeming afterthought — Freitas

does not explain why he thinks the comment was improper.                   And he

does not cite any authority to support his claim (nor does he

explain   the     nonexistence    of    authority,      assuming    he   unearthed

none).    So we hold it waived.             See Zannino, 895 F.2d at 17; see

also Rodríguez, 659 F.3d at 175-76.

                                       - 27 -
                                 Sentencing

            At    sentencing,    the   prosecutor   argued   (among    other

things) that the judge could reasonably infer that the offenses of

conviction were not the only time Freitas had helped Rafael get

cash out of the country.        This is what the prosecutor said:

          Now we don't know if this is the only time Mr.
     Freitas did this. I would suggest that it's not for two
     reasons.    In his conversations with the undercover
     agents, Mr. Rafael talks about having someone at the
     airport who helps him do this. The scenario he describes
     is not the scenario for which Mr. Freitas was prosecuted,
     the scenario Mr. Rafael describes is that he gives money
     to Mr. Freitas, Mr. Freitas goes through the secure areas
     of the airport with the money, while Rafael goes through
     the TSA checkpoint, and they meet in the bathroom in
     Terminal E, near the gate area, where Mr. Freitas gives
     the money back to Mr. Rafael. He describes it in detail.
     I can't prove that that occurred, but there is strong
     circumstantial evidence that this is not the only time
     that Mr. Freitas did this.

          Second, we know that, on at least one other
     instance, Mr. Freitas went to the airport to help Mr.
     Rafael smuggle money, that was November of 2015, he did
     not in fact do so on that date. But there's a lot of
     smoke here besides the incident for which Mr. Freitas
     actually stands convicted.    And I would suggest that
     first the fact that it appears he may have done this on
     additional occasions and, two, the fact that he's a state
     and federal law enforcement officer, militates in favor
     of a sentence of incarceration. And in the government's
     view a year and a day would be a proportional sentence.

            Freitas's lawyer did not object then but now contends

that the prosecutor's argument improperly went beyond the evidence

at trial.        We review this new claim only for plain error, as

Freitas admits we should.       See Edelkind, 467 F.3d at 797.        But as

                                   - 28 -
the government stresses, a problem for him is that after the

prosecutor made his sentencing pitch, the judge asked defense

counsel to focus his sentencing recommendation on Freitas's status

as a law-enforcement officer.    And the judge also indicated that

the "other conduct" stuff would not be the driving force behind

the sentence.   A further problem for him is that in explaining the

thinking behind the year-and-a-day sentence, the judge emphasized

Freitas's law-enforcement position but said nothing suggesting

that he gave weight to the "other conduct" stuff. So even assuming

(purely for argument's sake, mind you) an error that was plain,

Freitas cannot show prejudice — which means he cannot surmount a

prominent hurdle to plain-error relief.   See id.

                              WRAP UP

          Our work over, we affirm the judgment that entered below.

                                - 29 -