United States of America v. Antonio M. Freitas

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

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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."

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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

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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.

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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.

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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

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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

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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).

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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

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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.

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(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.

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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:

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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

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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

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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

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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

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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).

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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

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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."

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§ 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.

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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

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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

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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

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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

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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

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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

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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.

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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

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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.

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