United States v. Shafa

• Court: Court of Appeals for the First Circuit
• Decided: April 24, 2026
• Docket: 25-1146
• Status: Published

Opinion

United States Court of Appeals For the First Circuit

No. 25-1146

UNITED STATES,

Appellee,

v.

RAHIM SHAFA,

Defendant, Appellant.

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

[Hon. Margaret R. Guzman, U.S. District Judge]

Before

Barron, Chief Judge, Lipez and Rikelman, Circuit Judges.

Martin G. Weinberg, with whom Michael Pabian was on brief, for appellant. Karen L. Eisenstadt, Assistant U.S. Attorney, with whom Leah B. Foley, United States Attorney, was on brief, for appellee.

April 24, 2026 BARRON, Chief Judge. In this appeal, Rahim Shafa

("Shafa") seeks to overturn his federal convictions for

international money laundering and/or aiding and abetting the

same, importing merchandise contrary to law and/or aiding and

abetting the same, and receipt and delivery of misbranded drugs.

The convictions relate to his operation and ownership of a

Massachusetts-based clinic that provided patients with imported

drugs to treat addiction. He was sentenced for each of these

convictions to a term of 36 months of imprisonment, with each

sentence to be served concurrently.

Shafa contends that his convictions must be vacated due

to errors that the United States District Court for the District

of Massachusetts made in determining the evidence that could be

admitted at his criminal trial. He separately argues that his

sentences cannot stand due to errors that the District Court made

in applying the United States Sentencing Guidelines

("Guidelines"). We affirm Shafa's convictions but vacate his

sentence for misdemeanor misbranding. We also retain jurisdiction

over this appeal as to his challenges to his other sentences while

remanding the case for further consideration consistent with this

decision. On remand, the District Court is directed to clarify

the basis for its determination that § 2B1.1 of the Guidelines,

which is commonly known as the fraud guideline, applied to Shafa.

- 2 - I.

The Food, Drug, and Cosmetic Act ("FDCA"), 52 Stat. 1040,

as amended, 21 U.S.C. § 301 et seq., regulates, among other things,

the manufacture, labeling, and distribution of prescription drugs

shipped or received in interstate commerce.1 Under the FDCA, a

prescription drug is "misbranded" if "at any time prior to

dispensing the label of the drug fails to bear, at a minimum, the

symbol 'Rx only.'" 21 U.S.C. § 353(b)(4). Any such drug will

also be deemed "misbranded" under 21 U.S.C. § 352(b) if it is

packaged without a label bearing both the "name and place of

business of the manufacturer, packer, or distributor" and "an

accurate statement of the quantity of the contents in terms of

weight, measure, or numerical count." In addition, any such drug

will be deemed "misbranded" under 21 U.S.C. § 352(f)(1) if its

label does not have "adequate directions for use."

21 U.S.C. § 331(c) criminalizes the "receipt in

interstate commerce of any . . . drug . . . that is . . .

misbranded, and the delivery or proffered delivery thereof for pay

or otherwise." The FDCA further provides in § 333(a)(2) that "if

any person commits" a violation of 21 U.S.C. § 331 "with the intent

1 A prescription drug, as relevant here, is a drug that is intended for human use and, "because of its toxicity or other potentiality for harmful effect, or the method of its use, or the collateral measures necessary to its use, is not safe for use except under the supervision of a practitioner licensed by law to administer such [a] drug." 21 U.S.C. § 353(b)(1)(A).

- 3 - to defraud or mislead, such person shall be imprisoned for not

more than three years or fined not more than $10,000, or both."

On July 8, 2021, following an earlier indictment, a

superseding indictment was handed up in the District of

Massachusetts against Shafa and his wife, Nahid Tormosi Shafa.

That indictment charged them with federal crimes related to their

involvement with misbranded drugs and alleged, in relevant part,

as follows.

Shafa was a professional psychiatrist who owned Novel

Psychopharmacology ("Novel"), a clinic with two locations in

Massachusetts that provided treatment for those suffering from

drug addiction. The U.S. Food and Drug Administration ("FDA") had

approved drugs containing disulfiram as an active ingredient to

combat alcohol addiction and drugs containing naltrexone as an

active ingredient to combat alcohol and opioid addiction. However,

the FDA had approved only tablets containing disulfiram and only

tablets and injectable liquids containing naltrexone.

Nonetheless, Shafa and his wife, who managed Novel, ordered

naltrexone pellet implants, disulfiram injections, and disulfiram

pellet implants from Wayne Moran, a doctor in Hong Kong, for

delivery in the United States.

Thereafter, on or about June 30, 2016, Shafa and his

wife imported the purchased naltrexone pellet implants. Then, on

or about November 17, 2017, they imported more of the purchased

- 4 - naltrexone pellet implants as well as naltrexone injections and

disulfiram pellet implants.2 Finally, on or around January 3,

2018, they imported more of the disulfiram pellet implants.

In each instance, a package was shipped into the United

States. Each package contained the relevant items but was

accompanied by shipping documents and a packing slip that described

the contents as "plastic beads in plastic tubes" and misstated the

value of the contents of the package.

Shafa and his wife pleaded not guilty to the charges

against them. They were tried jointly in the District of

Massachusetts beginning on January 23, 2024. The jury acquitted

Shafa's wife on all counts. It acquitted Shafa on a number of

counts but found him guilty on the others.

Specifically, the jury found Shafa guilty of three

counts of international money laundering, and/or aiding and

abetting the same, in violation of 18 U.S.C. §§ 1956(a)(2)(A) and

2. Each of these three counts pertained to one of the shipments

described above and was for transferring a monetary instrument or

funds abroad with the intent to carry on unlawful activity. The

unlawful activity was importing merchandise in violation of either

2 Thesuperseding indictment alleges, in multiple places, that Shafa purchased and imported naltrexone injections, which -- unlike the disulfiram injections or naltrexone pellets -- are FDA-approved. However, Shafa does not argue that these allegations bear on this appeal.

- 5 - 21 U.S.C. § 331(a) (barring introduction or delivery into

interstate commerce of any misbranded drug) or 18 U.S.C. § 541

(barring entry of falsely classified goods).

In addition, the jury found Shafa guilty of three counts

of importing merchandise contrary to law, and/or aiding and

abetting the same, in violation of 18 U.S.C. §§ 545 and 2. Again,

each count pertained to one of the shipments described above. The

importation was alleged to be contrary to law because it violated

either 21 U.S.C. § 331(a) or 18 U.S.C. § 541.

Finally, the jury found Shafa guilty of one count of

receipt and delivery of misbranded drugs, in violation of 21 U.S.C.

§ 331(c). The jury also found, however, that he had acted without

intent to defraud as to the misbranding, making the conviction for

misdemeanor, not felony, misbranding. See 21 U.S.C. § 333(a).

On December 16, 2024, the District Court sentenced

Shafa. After calculating his recommended sentencing range under

the Guidelines to be 63 to 78 months of imprisonment, the District

Court imposed a sentence of 36 months of imprisonment for each

offense, with each sentence to be served concurrently.

Shafa timely appealed.

II.

Shafa's challenges to his convictions concern errors

that the District Court assertedly made in determining the evidence

that could be admitted at trial. In this Part, we consider the

- 6 - challenges that Shafa brings to his convictions in which he takes

aim at the District Court's refusal to admit into evidence

testimony from Moran.

A.

This set of challenges concerns testimony that Moran

gave in a prior federal criminal case, but that Shafa wanted to

introduce as evidence at trial in his case. The defendant in that

earlier case, which was tried in California, was a different

doctor -- Lance Gooberman. Like Shafa, Gooberman had been charged

with several federal criminal offenses related to the unlawful

importation of naltrexone pellets into the United States. See

United States v. Gooberman, No. CR 20-125-JFW (C.D. Cal.)

(hereinafter, "the Gooberman trial").

In its case against Gooberman, the government called

Moran as a witness. Moran testified that he had purchased

naltrexone pellets from Gooberman, conveyed the pellets to a

medical storage facility in Hong Kong (named United Mail Order),

repackaged and labeled the products, and then had United Mail Order

convey the pellets to patients who were being treated for addiction

both at his clinics in Hong Kong and in other countries. He

further testified that when he shipped the repackaged naltrexone

pellets, he instructed United Mail Order to describe the products

as "plastic beads and plastic tubes" instead of as naltrexone

pellets on the shipping label and documents. He also testified

- 7 - that he chose this description for the shipping label "[b]ecause,"

"[t]he first time[] they were stopped in customs in Anchorage," "a

customs official in Anchorage told [his] practice manager that

that's what they should be labeled as in order to be able to be

delivered to Boston, to a doctor in Boston."

In his case, Shafa filed a motion in limine with the

District Court to admit the Moran testimony from the Gooberman

trial into evidence at his own trial. Shafa made the motion

pursuant to Federal Rule of Evidence 804(b)(1). Under that rule,

hearsay is admissible if the declarant is "unavailable to testify

in person" and "the opposing party had 'an opportunity and similar

motive to develop the testimony by direct, cross, or redirect

examination.'" United States v. Bartelho, 129 F.3d 663, 670 (1st

Cir. 1997) (quoting Fed. R. Evid. 804(b)(1)).

The District Court denied the motion. It first observed

that Moran was "not physically present" and then observed that

"the person" (referring to the U.S. Customs official in Anchorage)

"who he testified that he relied on the information from [wa]s

neither named nor [wa]s he willing to tell [the Court]." The

District Court also noted that Moran "d[idn't] stand in the same

place in this case as he did in that case," and it expressed the

concern that "to allow [the District Court] to use testimony and

ask the jurors to rely on it" would require "first . . . giv[ing]

them the caveats of why it's not the same," which "[defeats] the

- 8 - whole purpose of providing testimony." It then stated that the

testimony was "too confusing" and "too iffy" to admit.

The government, like Shafa, proceeds as though the

District Court determined that the Moran testimony in question was

not admissible under Rule 804(b)(1). It then contends that our

review of that determination by the District Court is only for

plain error because Shafa did not make the precise argument to the

District Court that he now makes to us about why the Moran

testimony from the Gooberman trial was admissible under that rule.

Shafa disagrees on this point and argues that his

Rule 804(b)(1) challenge is preserved. We may skip over the

parties' dispute about forfeiture because, even if we were to

assume that Shafa did preserve this challenge, we do not agree

with Shafa's contention that the District Court abused its

discretion in rejecting the Moran testimony. See United States v.

Colón-Díaz, 521 F.3d 29, 33 (1st Cir. 2008) ("Evidentiary rulings

. . . are ordinarily reviewed for abuse of discretion.").

The parties appear to agree that Moran was not available

to testify as a witness in Shafa's case. They thus agree that the

key question on appeal concerns whether the government's motive to

develop Moran's testimony in the Gooberman trial was similar to

the motive that it had to develop that testimony in the trial in

Shafa's case. See Fed. R. Evid. 804(b)(1).

- 9 - To answer that question, we first must assess "whether

the questioner is on the same side of the same issue at both

proceedings." Bartelho, 129 F.3d at 671 (quoting United States v.

DiNapoli, 8 F.3d 909, 912 (2d Cir. 1993) (en banc)). We then must

consider "whether the questioner had a substantially similar

interest in asserting that side of the issue." Id. (quoting

DiNapoli, 8 F.3d at 912).

The government concedes that it was on the same side of

the issue at both proceedings. Thus, we need to address only the

second inquiry. Shafa argues as to that inquiry that the

government had a "similar, indeed virtually identical" interest in

both cases in "challenging Moran's testimony on this issue." He

thus argues that the testimony was admissible under

Rule 804(b)(1).

Shafa recognizes that in the Gooberman trial the

government did not explore the Moran testimony in depth or

challenge its veracity. But Shafa argues that the government's

decision not to question Moran more vigorously in the Gooberman

trial was merely a "tactical decision." Bartelho, 129 F.3d at 672

n.9. For that reason, Shafa contends that the government's manner

of questioning Moran in the Gooberman trial fails to show that the

government had a different interest in questioning Moran in that

case than it had in questioning him in this case. See id. ("A

purely tactical decision not to develop particular testimony

- 10 - despite the same issue and level of interest at each proceeding

does not constitute a lack of opportunity or a dissimilar motive

for purposes of Rule 804(b)(1)."

We are not convinced. In the Gooberman trial, Moran was

a witness for the government. Thus, as the government contends,

it needed Moran's "testimony and credibility . . . to connect the

defendant to the imports." In consequence, as the government well

explains, in that earlier trial it "had almost no interest in

probing or challenging the story's historical veracity [regarding

the supposed statement by the federal customs agent in

Alaska] . . . because to do so would have undermined Moran's

credibility and . . . the government's case, at least in part,

relied on Moran's credibility." By contrast, the government

contends that in Shafa's case it "was not similarly hamstrung . . .

because Moran's credibility was not necessary to connect Shafa to

the importations." So, the government reasons, if Moran had

testified at Shafa's trial, then it would have had "every reason"

to ask "obvious follow-up questions" that it did not ask in the

Gooberman trial. Those questions would have included "whether

Moran could recount exactly what his practice manager said, why

Moran then started bringing implants into the country on his person

rather than shipping them . . . , and whether the alleged Customs

official also said it was appropriate to grossly undervalue the

implants on the shipping documents."

- 11 - We agree with the government's reasons for contending

that it lacked the "intensity of interest" in discrediting Moran's

testimony in the Gooberman trial that it had in Shafa's. Shafa's

Rule 804(b)(1) challenge therefore fails. See Bartelho, 129 F.3d

at 671 (noting that "the government's motive as prosecutor in

developing testimony and presenting evidence may vary from case to

case" (citing United States v. Salerno, 505 U.S. 317, 324-25

(1992))).

B.

Shafa separately advances two other arguments as to why

the District Court erred in denying his motion in limine to admit

the Moran testimony. We are not convinced by either one.

1.

Shafa first argues that, Rule 804(b)(1) aside, Moran's

testimony was admissible under Federal Rule of Evidence 106. Under

that rule, "[i]f a party introduces all or part of a statement,"

then "an adverse party may require the introduction, at that time,

of any other part -- or any other statement -- that in fairness

ought to be considered at the same time." Fed. R. Evid. 106.

This argument rests on the fact that, at Shafa's trial,

the government introduced into evidence email communications that

Shafa had with Moran regarding the "plastic beads in plastic

tubes." Shafa reasons that, because Moran's testimony from the

Gooberman trial explained the origin of why the materials at issue

- 12 - were described as "plastic beads in plastic tubes," the District

Court was required under Rule 106 to permit the Moran testimony to

be admitted into evidence for completeness.

Even if we were to assume that this argument had been

raised below, such that our review would be for abuse of

discretion, see Colón-Díaz, 521 F.3d at 33, the argument is without

merit. Before otherwise inadmissible evidence may be admitted

into evidence for completeness pursuant to Rule 106, a

"preliminary decision must be made as to what grouping constitutes

a fair and reasonably complete unit of material." United States

v. Boylan, 898 F.2d 230, 257 (1st Cir. 1990). As the government

points out, the statements that Moran made in his testimony at the

Gooberman trial were not made in any of the emails that the

government introduced into evidence at Shafa's trial. Moran's

testimony in the Gooberman trial also did not refer to any of the

emails that Moran sent to Shafa and that were then admitted into

evidence at Shafa's trial. We therefore fail to see how it was an

abuse of discretion to determine that the Moran testimony was not

part of a "grouping [that] constitutes a fair and reasonably

complete unit of material." Id.

2.

The other ground that Shafa relies on to argue that,

Rule 804(b)(1) aside, the District Court erred in excluding

Moran's testimony in the Gooberman trial from Shafa's trial rests

- 13 - on "the Constitutional guarantee of 'a meaningful opportunity to

present a complete defense.'" (Quoting Crane v. Kentucky, 476

U.S. 683, 690 (1986)). Shafa explains that "where constitutional

rights directly affecting the ascertainment of guilt are

implicated, the hearsay rule may not be applied mechanistically to

defeat the ends of justice." Chambers v. Mississippi, 410 U.S.

284, 302 (1973). He then asserts that "Chambers applies here,

given that Moran's prior testimony was powerfully

exculpatory . . . and carried significant guarantees of

trustworthiness including having been provided 'under oath' and

subject to examination by the government." (Quoting id. at 298.)

Assuming that Shafa preserved this challenge, our review

is for abuse of discretion. See Colón-Díaz, 521 F.3d at 33. Shafa

has not made the required showing under that standard of review.

Unlike in Chambers, the excluded evidence here is not a

confession. See 410 U.S. at 300. It is the reported statement of

an unnamed customs official, filtered to Moran through his practice

manager, who, because he had died, was an unavailable witness. We

thus do not see how this case is remotely like Chambers, and Shafa

does not explain why, despite that difference, the Moran testimony

falls within the scope of Chambers. Accordingly, this ground for

challenging the District Court's exclusion of Moran's prior

testimony fails.

- 14 - III.

We now turn our attention to Shafa's contentions that

his convictions must be vacated because the District Court erred

by admitting certain testimony into evidence at his criminal trial

that should have been excluded pursuant to Federal Rules of

Evidence 401 and 403. These challenges also do not provide a basis

for disturbing Shafa's convictions.

Under Rule 401, evidence is relevant if it has "any

tendency to make a fact [of consequence] more or less probable."

Fed. R. Evid. 401. As a result, "[a] relevancy-based argument is

usually a tough sell." Bielunas v. F/V Misty Dawn, Inc., 621 F.3d

72, 76 (1st Cir. 2010). We review preserved challenges to

determinations about relevancy only for abuse of discretion, as

"we give trial judges considerable leeway in deciding whether the

contested evidence satisfies this not-too-difficult-to-meet

standard." Id.

Under Rule 403, evidence must be excluded if "its

probative value is substantially outweighed by a danger

of . . . unfair prejudice" or "misleading the jury." Fed. R.

Evid. 403. Here too, our review is only for abuse of discretion,

even if the challenge is preserved. See Old Chief v. United

States, 519 U.S. 172, 183 n.7 (1997). And, here too, the showing

is hard to make, as we have explained that "[o]nly rarely -- and

- 15 - in extraordinarily compelling circumstances -- will we, from the

vista of a cold appellate record, reverse a district court's

on-the-spot judgment concerning the relative weighing of probative

value and unfair effect." United States v. Sabetta, 373 F.3d 75,

82-83 (1st Cir. 2004) (quoting United States v. Smith, 292 F.3d

90, 99 (1st Cir. 2002)).

Shafa takes issue under Rules 401 and 403 with the

District Court's decision to admit into evidence testimony

provided by a number of witnesses. Among those witnesses were

three students who interned at Shafa's office -- Nicole Petrosky,

Mary DeVivo, and Elizabeth Knight. The other witnesses that these

challenges concern were Shafa's former receptionist, Julia

Taranto, and Shafa's former patients: Katrina Calamonici,

Christine Repetto, and Karen Bertoni.

Shafa contends that the "vast majority" of the testimony

from these witnesses that he challenges "reflected a broad-based

critique of [him] and his medical practice" even though he was

"not charged with practicing medicine outside of professional

norms." As a result, Shafa argues, the testimony of these

witnesses lacked "any tendency to make a fact [of consequence]

more or less probable," (alteration in original) and so did not

constitute relevant evidence under Rule 401. He further argues

that their testimony was inadmissible under Rule 403 to the extent

that it had "minimal probative value" because "any such probative

- 16 - value was 'substantially outweighed' by the danger of 'unfair

prejudice.'"3

We come, then, to Shafa's unpreserved challenges under

Rules 401 and 403 to the District Court's decision to permit the

government to provide testimony from Shafa's former students and

former patients. Shafa describes the students' testimony to us as

follows: The former students stated that he "provided insufficient

supervision, performed pellet implant procedures in a dark, dirty

room with insufficient sterilization (in one instance using an

expired anesthetic), and even fell asleep during patient

appointments." Shafa further asserts that the former patients, in

their testimony, described "their struggles with

addiction . . . , the wait times to see the doctor (with one

witness testifying she waited 12 hours), the intrusive nature of

the implant procedures, medical complications they suffered (and

in some cases continued to suffer) as a result, and their relapsing

after being treated by Shafa."

3 Although Shafa asserts that the challenged testimony constituted testimony about "uncharged bad acts," he makes no argument that even if the testimony were admissible under Rule 401 and 403, it was inadmissible under Rule 404(b). See Fed. R. Evid. 404(b). We therefore treat any such argument as waived. See United States v. Zannino, 895 F.2d 1, 17 (1st Cir. 1990) ("We see no reason to abandon the settled appellate rule that issues adverted to in a perfunctory manner, unaccompanied by some effort at developed argumentation, are deemed waived.").

- 17 - Shafa did not specifically challenge any of this

testimony below under either Rule 401 or Rule 403. So, our review

is only for plain error. See United States v. Watson, 695 F.3d

159, 162 (1st Cir. 2012). We see none because this testimony,

too, either bore on Shafa's intent, was cumulative of other

admitted evidence, or lacked the emotionally charged content that

would make it plain that its prejudicial impact substantially

outweighed its probative value. See Sabetta, 373 F.3d at 82-83

(quoting Smith, 292 F.3d at 99).

C.

Shafa preserved objections under Rules 401 and 403 to

certain statements that Petrosky, DeVivo, Taranto, and Repetto

made in their testimony. Specifically, he preserved objections

to: (1) the statement by Petrosky that he would wear a mask "[t]o

avoid contaminating the area and breaking sterile field"; (2) the

statements by DeVivo that "sterile drapes are typically a one-time

use drape . . . . and the package should only be opened once[,]

and then once you're done, you should throw them away. And [she]

distinctly remember[ed] them being . . . previously opened because

that's very unusual" and explaining that "[i]t's unusual because

they should be sealed, and it should be opened every time you do

a procedure"; (3) the statements by Taranto that "[t]here's just

no way" that the clinic "could have been sterile because patients

were seen in that room throughout the day. And then there was

- 18 - nobody to go in and sterilize the room before an implant was done";

and (4) the statements by Repetto that she did not think "Shafa

engaged in mutual collaborative team work with [her]" because "[she

had] been to many doctors in [her] life that specialize in

addiction or psychopharmacology" and that she had "felt mutual

. . . collaborative team work . . . . before with doctors very

well" but that she "did not feel that [with Shafa] -- [she] felt

like [she] was being sold something basically."

Although Shafa contends otherwise, the District Court

did not abuse its discretion in determining that these statements

cleared the low bar for relevance. See Bielunas, 621 F.3d at 76.

As the government explains, the statements "supported the

government's theory" that "Shafa knowingly smuggled and sold

misbranded drugs for profit without regard to patient safety" and

undermined Shafa's theory that, as framed by the government, he

was a "conscientious doctor who was just trying to help addicted

patients with effective treatment." And Shafa's opening statement

did frame the case to the jury as being about "a doctor, an MD,

dedicated to eradicating the scourge of opioid addiction" and "the

Food and Drug Administration's efforts to stop him."

We also agree with the government that the District Court

did not abuse its discretion in determining under Rule 403 that

the probative value of these statements was not substantially

outweighed by the danger of undue prejudice. See Sabetta, 373

- 19 - F.3d at 82-83 (quoting Smith, 292 F.3d at 99). As the government

explains, the challenged evidence was largely cumulative and not

sufficiently inflammatory to evoke an emotional response. See

United States v. Cruz-Ramos, 987 F.3d 27, 43 (1st Cir. 2021)

("[Rule 403] bans not all prejudice, but unfair

prejudice . . . and it does not save a defendant from damaging

evidence generally." (citation modified)).

D.

Shafa's last challenge pursuant to Rules 401 and 403

concerns the District Court's decision to admit into evidence the

testimony of Dr. Arthur Simone. That testimony included "the

concept of sterility" and Simone's assessment of the risks created

by the conditions that the former students and patients described,

such as "septic shock and death." The testimony also included

Simone's explanation that the FDCA stemmed from "an incident where

an antibiotic that was only available in tablet form was made into

an elixir form and given to children" but that, "[u]nfortunately,

the way they made it into that elixir form . . . . killed people."

Shafa argues that Simone's explanation of the origins of

the relevant FDCA provision "was readily comparable to Shafa's use

of naltrexone" in an unapproved form. Shafa claims on that basis

that Simone's testimony "fit neatly into the government's repeated

(but irrelevant) assertion that the FDCA requirements Shafa

allegedly violated were intended to protect patients from harm."

- 20 - As far as we can tell, this challenge is unpreserved and

so is subject to review only for plain error. See Watson, 695

F.3d at 162. Shafa's claim amounts to an argument that, "[i]n

light of the government's failure to articulate any theory of

relevance to the charged offenses, and the significant potential

for unfair prejudice, admission of" this testimony was "clear and

obvious error." But, as we have explained, the government asserted

that this evidence was relevant to disputing Shafa's theory of the

case. And we agree with the government both that testimony about

the history of the FDCA was "relevant as context for Simone's

testimony about the regulatory framework" and that Simone's

testimony about sterility was "relevant to evaluating the factual

evidence about Shafa's implant surgeries."

Shafa does also argue that, even if relevant, the

testimony was unduly prejudicial "given [its] extensiveness and

emotionally charged nature." But he does not explain how a

doctor's testimony about sterility is so emotionally charged as to

be unfairly prejudicial. Thus, we do not agree that the District

Court committed clear or obvious error under Rule 403 in admitting

this testimony.

IV.

We now turn to the challenges in which Shafa takes issue

with the District Court's decision to admit into evidence what he

contends was undisclosed expert testimony and testimony that set

- 21 - forth legal conclusions. We see no grounds for overturning Shafa's

convictions based on these challenges.

We start with the challenges to the testimony that the

three former students who were called by the government as lay

witnesses gave that Shafa contends reflected "specialized

knowledge" that only a witness qualified as an expert may provide.

Fed. R. Evid. 701 (prohibiting "lay witnesses" from testifying

"based on scientific, technical, or other specialized knowledge

within the scope of Rule 702"). Shafa points to the following

statements that the students made in their testimony:

(1) "To ensure sterility, when you're treating a patient, you don't touch anything with your gloves that's not clean. So if there is a tube of bacitracin, you would have someone else either put it on a Q-Tip that's sterile or put it on a gauze that's sterile, and then you would use that to apply it to the area";

(2) "[T]here's a kind of concept in surgery of maintaining sterility, and that's to prevent infection. . . . [S]terile drapes are . . . one-time use, and the package should only be opened once; and then once you're done, you should throw them away"; and

(3) "Any time you open the skin, there's a risk of bacteria getting underneath the skin and causing an infection in that area, whether that be localized or throughout the body. Because of the lack of cleaning, whether that be through the room or washing hands, lack of personal protective equipment, there was . . . a significantly higher likelihood of causing an infection for the patient."

- 22 - Shafa points out that each of these witnesses not only

provided testimony concerning sterility but also "went on to

testify that Shafa's implant procedures did not comply with

sterility requirements." He also notes that one of these witnesses

additionally testified that the unclean conditions in which Shafa

treated patients at his clinic could cause infection and

potentially "devastating consequences."

As these challenges to this testimony were not made

below, our review is only for plain error. See Watson, 695 F.3d

at 162. Shafa has not met his burden under that demanding

standard.

Shafa acknowledges that "Simone also testified regarding

the concept of sterility," and we have explained that Shafa failed

to show how admission of that testimony was plain error. "We have

held that 'no substantial right of the party is affected where the

evidence admitted was cumulative as to other admitted evidence.'"

United States v. Perrota, 289 F.3d 155, 165 (1st Cir. 2002)

(quoting Doty v. Sewall, 908 F.2d 1053, 1057 (1st Cir. 1990)).

Specifically, the portions of the challenged testimony that were

based on the students' medical training, like the need to sterilize

equipment or operating environments, the use of sterile drapes, or

the risks of infection, were cumulative of Simone's testimony on

sterility and sterilization.

- 23 - Moreover, "under Rule 701, a layperson can offer an

opinion if it is 'rationally based on the witness's perception,'"

United States v. Pontz, 132 F.4th 10, 19 (1st Cir. 2025) (quoting

Fed. R. Evid. 701), even when that testimony is "based on the lay

expertise a witness personally acquires through experience, often

on the job," id. (quoting United States v. Maher, 454 F.3d 13, 24

(1st Cir. 2006)).4 Shafa fails to explain why it is clear or

obvious that this exception does not encompass the challenged

testimony by these witnesses that is not cumulative of Simone's

testimony about sterility. After all, that non-cumulative portion

of the challenged testimony is based on the medical students'

first-hand observations about the conditions in Shafa's office.

That brings us to Shafa's contention that the District

Court committed reversible error by admitting into evidence

testimony from two witnesses whom the government called -- Simone

and Tenzing Rapgyal, a U.S. Customs and Border Protection import

4 We construe Shafa's contention that if these witnesses had been qualified as experts, then Shafa would have received mandatory pre-trial disclosures under Federal Rule of Criminal Procedure 16(a)(1)(G), as an attempt to show that he was prejudiced by the Rule 701 error that he claims. See Fed. R. Crim. P. (16)(a)(1)(G) (explaining the pre-trial disclosure obligations for expert testimony sought to be admitted under Federal Rules of Evidence 702, 703, or 705). But Shafa does not explain how he was prejudiced by being denied such disclosure if he would not have been prejudiced by the witnesses testifying about sterility. Accordingly, this ground for showing prejudice fails as well.

- 24 - specialist -- in which the witnesses assertedly "recit[ed] and

interpret[ed] the law applicable to misbranding and

unlawful-importation charges against Shafa (which, in turn, served

as predicates for the money-laundering charges)." We first

consider the aspect of this challenge that targets Simone's

testimony. We then will consider the aspect of this challenge

that targets Rapgyal's testimony.

Shafa takes issue with the Simone testimony because he

contends that it impermissibly gave a legal definition of

misbranding and affirmed both that an "unapproved prescription

drug" would constitute "misbranding" and that "a drug product

containing naltrexone" or disulfiram would be "considered a

prescription drug" (which implicated FDCA regulations). Shafa

does not dispute that "much" of this testimony "was reflected in

the [D]istrict [C]ourt's subsequent instructions." Nonetheless,

he contends that the testimony was prejudicial because the

"repetition" of these "instructions" "via a government witness

carried the predictable risk of emphasizing the points and

inappropriately enhancing the credibility of Simone, and the

government's case as a whole."

Shafa adds that some of the assertedly impermissible

testimony was prejudicial for the distinct reason that it did not

merely repeat a legal conclusion that was already set forth in the

- 25 - jury instructions but instead set forth a new one. Here, he points

to testimony that he contends amounts to Simone describing that

there is strict liability for unapproved naltrexone and disulfiram

products.

Shafa did not preserve this challenge to Simone's

testimony below. As a result, our review is only for plain error.

See Watson, 695 F.3d at 162. We see none.

Shafa is right that we have long held that it is

impermissible for "witnesses to instruct the jury as to applicable

principles of law." Nieves-Villanueva v. Soto-Rivera, 133 F.3d

92, 99 (1st Cir. 1997) (quoting United States v. Newman, 49 F.3d

1, 7 (1st Cir. 1995)). But, as the government notes, we also have

held that a witness may provide expert testimony about a regulatory

framework in some circumstances even though that testimony

describes certain legal provisions. See United States v. Galatis,

849 F.3d 455, 462 (1st Cir. 2017) (allowing expert testimony that

"aided the jury in understanding the regulatory framework").

Based on Shafa's arguments on appeal, we are not

convinced that it is "clear or obvious" that Simone's testimony

falls on the impermissible side of our precedent. Watson, 695

F.3d at 163; cf. Galatis, 849 F.3d at 461-62 (finding the District

Court did not abuse its discretion by allowing lay witnesses to

"testify as to their understandings of certain Medicare terms").

In addition, given the ample evidence that the drugs at issue were

- 26 - misbranded, Shafa fails to make a convincing argument that the

decision to admit Simone's testimony that an unapproved

prescription drug would be deemed misbranded affected the outcome

of the case. He therefore has not met his burden to show plain

error.

As for the Rapgyal testimony, Shafa argues that it

impermissibly asserted that, under the federal statute governing

the invoicing of imported goods, "the label" of a package being

imported "has to describe . . . what the merchandise" in the

package is because "it's the law" under "19 U.S.C. § 1481." He

further challenges the testimony insofar as it went on to explain

that (1) the description of the contents of each package that the

package's label provided -- namely, "plastic beads and plastic

tubes" -- did not match the contents; (2) the value declared for

the contents of each package did not match the purchase price on

the invoices, as federal law required; and (3) "the Modernization

Act of 1993 clearly states that the importer or the person who is

bringing . . . that merchandise into the country is ultimately

responsible for the declared value, the classification, and

everything related to that shipment."

Shafa argues that Rapgyal's testimony "that the

descriptions [on the labels of each package] were false" was

prejudicial. He contends that it "amounted to a legal conclusion

- 27 - highly suggestive of Shafa's guilt," even though "that opinion was

far from inevitable" because the evidence supportably indicated

that each package in fact contained "plastic beads in plastic

tubes." He also contends that the testimony "that the importer,

here Shafa, was legally responsible for the accuracy of the

shipping documentation" was prejudicial because it "improperly

undermined the defense['s] argument that it was Moran, not Shafa,

who devised and utilized the description at issue."

Because Shafa did not raise below the ground that he

advances on appeal for challenging this testimony, our review is,

once again, only for plain error. See Watson, 695 F.3d at 162.

Once again, we see none.

The only challenged statements by Rapgyal that arguably

set forth legal conclusions were his statements that a federal

statute requires labels on merchandise being imported to describe

the contents of the package, that the importer is responsible for

the accuracy of the declarations, and that the descriptions on the

packing labels were false. As to the first two statements, as we

explained above, although we have found it impermissible for

witnesses to "instruct the jury as to applicable principles of

law," Nieves-Villanueva, 133 F.3d at 99 (quoting Newman, 49 F.3d

at 7), we have also recognized that some experts may testify about

regulatory frameworks, see Galatis, 849 F.3d at 462. And yet, as

with the testimony that Simone provided, Shafa develops no argument

- 28 - to us as to why it is clear or obvious that Rapgyal's testimony

was "solely to establish the meaning of a law," United States v.

Prigmore, 243 F.3d 1, 18 n.3 (1st Cir. 2001) ("[E]xpert testimony

proffered solely to establish the meaning of a law is presumptively

improper." (emphasis added)), rather than to explain a regulatory

framework. Shafa thus fails to establish plain error.

As to the statement that the descriptions on the packing

label were false, we do not see how it could have been prejudicial.

Shafa argues that the testimony was "highly suggestive" of an

opinion that was "far from inevitable" because there was evidence

to suggest that the "plastic beads in plastic tubes" description

was correct. However, given the other evidence in the record from

which a jury could find that the descriptions on the commercial

invoices were false, Shafa needs to explain why his substantial

rights were nonetheless affected. He fails to do so.

Shafa's final claim of trial error is that the District

Court wrongly precluded him from calling witnesses to provide

expert testimony to counter the legal opinions that the government

elicited from witnesses that it had called. This challenge targets

all his convictions other than his conviction for receipt and

delivery of misbranded drugs.

Prior to trial, Shafa sought to admit expert testimony

from regulatory attorney Benjamin England that "compounded

- 29 - naltrexone and disulfiram pellets . . . are not required to be

approved by the FDA" and are also "not required to bear adequate

directions for use." The District Court rejected Shafa's request.

Shafa contends that the District Court erred in doing

so. He reasons that this testimony was admissible to shore up his

contention that he lacked the requisite mens rea for the offenses

in question because he "believed the products" that he was

importing from Hong Kong "were compounded" -- as both the unlawful

importation and money laundering counts required the government to

prove that Shafa was "aware of the illegal nature" of the

merchandise in question.

As support for this argument, Shafa asserts that, if he

believed the products in question were compounded and therefore

not subject to the same regulations as drugs that are not

compounded, then he would not have been "aware of the illegal

nature" of his actions. Thus, he argues, "the jury should have

been permitted to hear England's testimony regarding the FDA's

materially different regulation of compounded products to support

an argument that the government's proof failed to satisfy the mens

rea required for conviction of unlawful importation and money

laundering."

Shafa did not argue below, however, as he now does, that

England's testimony was relevant because it was probative of

whether Shafa was either aware of the unlawful nature of the

- 30 - merchandise (as required by the unlawful importation counts) or

acted with the intent to advance unlawful activity (as required by

the money laundering counts). He argued to the District Court

only that England's testimony was relevant because he

"anticipate[d]" that England would introduce evidence "that these

were compounded drugs." (Emphasis added.) In fact, at that time,

Shafa asserted in support of the testimony's relevance, that the

evidence showing as much included not only a tape recording in

which he stated that the drugs came from a compounding pharmacy

but also other exhibits that referred to the drugs as compounded.

Because Shafa has shifted his argument, the District

Court's decision not to admit the England testimony into evidence

is subject to review only for plain error. See Watson, 695 F.3d

at 162. In advancing the newly raised ground for admitting the

England testimony, Shafa appears to accept that there must be a

basis in the record that supports his belief that the compounding

exception applies to the drugs that he was charged with misbranding

and unlawfully importing. Yet, precisely because he raised a

distinct ground for having the England testimony admitted, he did

not ask the District Court to make the finding that he needs to

support this challenge. And, as our Court has made clear, a

defendant cannot show plain error based on findings that it did

not ask the District Court to make. See United States v.

Olivier-Diaz, 13 F.3d 1, 5 (1st Cir. 1993) ("Where the error

- 31 - defendant asserts on appeal depends upon a factual finding the

defendant neglected to ask the district court to make, the error

cannot be 'clear' or 'obvious' unless the desired factual finding

is the only one rationally supported by the record below.").

VI.

To this point, we have concluded that none of Shafa's

individual challenges provides a basis for overturning his

convictions. Shafa separately argues, however, that, when taken

together, the individual errors that occurred at his trial with

respect to the admission and exclusion of evidence were such that

they require us to overturn his convictions based on their

aggregate effect even if none of those errors does so on their

own. United States v. Sepulveda, 15 F.3d 1161, 1195-96 (1st Cir.

1993) ("Individual errors, insufficient in themselves to

necessitate a new trial, may in the aggregate have a more

debilitating effect."). We are not persuaded.

A claim of cumulative error can only succeed if there

were multiple errors, and, in our analysis thus far, we have not

identified any errors at all. That said, we did rely on prejudice

to dispose of the claims that the District Court erred by admitting

into evidence (1) what amounted to undisclosed expert testimony

from lay witnesses about the importance of sterility, and (2) a

statement from Rapgyal that amounted to legal conclusions. And we

did so without first deciding whether the District Court erred in

- 32 - doing so. We need not resolve, however, whether the District Court

did in fact err. Even if we were to deem the District Court to

have done so, we still see no basis for crediting Shafa's argument

that the convictions cannot stand due to cumulative error. The

weight of other testimony admitted during trial, including the

evidence of mislabeling and misrepresentations of Shafa's

shipments as well as the descriptions of the conditions in which

former patients received treatment, counsels against any such

determination. See id. at 1196 (finding that where the errors

"were not portentous," "were few and far between," "possessed no

special symbiotic effect," and where "the government's case was

very strong" in a lengthy trial, "the errors, in the aggregate,

d[id] not come close to achieving the critical mass necessary to

cast a shadow upon the integrity of the verdict"); see also United

States v. Padilla-Galarza, 990 F.3d 60, 86 (1st Cir. 2021) (finding

no cumulative error where "myriad trial errors . . . winnowed down

to a single claim" that had itself "been adjudged insufficient, on

its own, to warrant vacation of the jury's verdict.").

VII.

Having rejected all of Shafa's challenges to his

convictions, we now must address his challenges to his sentences.

We begin with his challenges to his sentences that he contends

were procedurally unreasonable. See United States v. Vinas, 106

F.4th 147, 152 (1st Cir. 2024) ("A sentence can be challenged on

- 33 - both procedural and substantive grounds."). In them, Shafa

challenges the sentences on the ground that the District Court

misapplied the Guidelines. See Gall v. United States, 552 U.S.

38, 51 (2007). We review a district court's interpretation and

application of the Guidelines de novo and its factfinding for clear

error. See United States v. Carvajal, 85 F.4th 602, 609 (1st Cir.

2023). We evaluate "judgment calls" for abuse of discretion. Id.

(quoting United States v. Ruiz-Huertas, 792 F.3d 223, 226 (1st

Cir. 2015)).

In calculating the sentencing range that the Guidelines

recommended in Shafa's case, the District Court drew on the

Presentence Investigation Report ("PSR"), which the U.S. Office of

Probation prepared. The PSR identified a single offense level for

Shafa's seven convictions because it grouped them pursuant to

§ 3D1.2 of the Guidelines.5 The convictions, it will be recalled,

were for one count of misdemeanor misbranding, three counts of

unlawful importation, and three counts of international money

laundering.

The District Court agreed with the PSR's determination

that Shafa's base offense level was six pursuant to § 2N2.1, which

5Section 3D1.2 states that "[a]ll counts involving substantially the same harm shall be grouped together into a single Group." U.S. Sent'g Guidelines Manual § 3D1.2 (U.S. Sent'g Comm'n 2024).

- 34 - is the guideline that applies to misbranding offenses. That

guideline includes a cross-reference to § 2B1.1, the fraud

guideline, when "the offense involved fraud." U.S. Sent'g

Guidelines Manual § 2N2.1(c)(1) (U.S. Sent'g Comm'n 2024).

The District Court, like the PSR, increased Shafa's

offense level by 12 levels based on § 2B1.1. It calculated this

increase pursuant to the fraud guideline's loss table, which

identifies the applicable increase to the base offense level in

relation to the magnitude of the "loss." See id. § 2B1.1(b)(1).

The District Court next increased Shafa's offense level

as follows: two levels because the offense involved ten or more

victims, see id. § 2B1.1(b)(2)(A)(i); two levels because the

offense involved the conscious or reckless risk of death or serious

bodily injury to another, see id. § 2B1.1(b)(16)(A); two levels

because Shafa knew or should have known the victims of the offense

were vulnerable, see id. § 3A1.1(b)(1); and two levels because

Shafa abused a position of public and private trust, see id.

§ 3B1.3. The District Court therefore determined that Shafa's

offense level was 26.

The District Court then considered Shafa's Criminal

History Category, which it determined was I. It therefore

determined that, given Shafa's offense level of 26, the recommended

sentencing range under the Guidelines was 63 to 78 months of

imprisonment. In imposing the sentence, the District Court varied

- 35 - downward and sentenced Shafa to 36 months of imprisonment for each

of his convictions, with each sentence to be served concurrently.

Shafa first challenges the District Court's decision to

apply § 2B1.1, the fraud guideline, in sentencing him. He relies

on a recent amendment to the "relevant conduct" guideline,

§ 1B1.3(c), which the parties refer to as the acquitted-conduct

amendment. It bars a district court from applying the Guidelines

based on conduct for which the defendant was acquitted by a federal

court "unless such conduct also establishes, in whole or in part,

the instant offense of conviction." Id. § 1B1.3(c).

Shafa contends that the acquitted-conduct amendment

applies in his case because, when he was acquitted of conspiracy

to defraud the United States and felony misbranding, he was

acquitted of the conduct that the District Court determined

"involved fraud." And, he further argues, that conduct did not

"establish[], in whole or in part, the instant offense of

conviction." Id. Our analysis follows.

Shafa's frontline contention under the acquitted-conduct

amendment depends on "the instant offense of conviction" in his

case being solely the offense of misdemeanor misbranding,

notwithstanding that he was also convicted of the offenses of

unlawful importation and international money laundering. In

- 36 - pressing this contention, Shafa argues that, because the jury did

not need to find that he engaged in any of his allegedly fraudulent

conduct to find the elements of misdemeanor misbranding satisfied

in his case, there is no basis on this record for finding that any

of that conduct "establishes[] in whole or in part" that offense.

Thus, Shafa argues, the acquitted-conduct amendment barred the

District Court from relying on that conduct in applying the fraud

guideline to him because he was acquitted of that conduct when he

was acquitted of conspiracy to defraud the United States and felony

misbranding.

To support the challenge's premise that the offense of

misdemeanor misbranding and only that offense is "the instant

offense of conviction" in his case, Shafa points to the District

Court's reliance on the PSR in calculating his sentencing range

under the Guidelines. He argues that, because the PSR relied on

the misbranding guideline in applying the fraud guideline to Shafa,

it follows from the District Court's reliance on the PSR that the

District Court treated the offense of misdemeanor

misbranding -- and only that offense -- as "the instant offense of

conviction."

We are not convinced. The misbranding guideline applies

whenever a defendant is convicted of unlawful importation and, as

- 37 - in Shafa's case, the contraband item was a misbranded drug.6 U.S.

Sent'g Guidelines Manual § 2T3.1(c)(1) (U.S. Sent'g Comm'n 2024).

We therefore do not see why it follows from the District Court's

reliance on the PSR that the District Court treated misdemeanor

misbranding rather than unlawful importation as "the instant

offense of conviction" in Shafa's case.

There is further reason to doubt Shafa's premise that

misdemeanor misbranding and only misdemeanor misbranding is "the

instant offense of conviction" in his case. The District Court

did not expressly identify misdemeanor misbranding (or, for that

matter, any other offense) as the "instant offense of conviction."

Nor did it impliedly do so by, for example, finding that Shafa's

conduct that "involved fraud" was conduct that "establishe[d], in

whole or in part" the offense of misdemeanor misbranding. Indeed,

the District Court suggested at one point that Shafa's conduct

that "involved fraud" was his conduct in committing the offense of

unlawful importation, and it noted at another point that "fraud is

not just one of the elements of Count Nine," which is the count

setting forth the misbranding charge.

6 The misbranding guideline applies to the offense of unlawful importation when the offense "involves a contraband item covered by another offense guideline," and that offense guideline (in this case, the misbranding guideline) yields a higher offense level than the unlawful importation guideline. U.S. Sent'g Guidelines Manual § 2T3.1(c)(1) (U.S. Sent'g Comm'n 2024). There is no dispute that the misbranding guideline would yield a higher offense level in this case.

- 38 - Shafa at times appears to be making a distinct argument

as to why we must conclude that the offense of misdemeanor

misbranding -- and only that offense -- is "the instant offense of

conviction" in his case. Here, Shafa points to the fact that the

guideline for the offense of unlawful importation does not include

a cross-reference to the fraud guideline, while the guideline for

the offense of misdemeanor misbranding does. He then goes on to

contend that, because some level of deception inheres in all

unlawful importation, "[i]f every mislabeled shipment could

support application of the fraud guideline," the unlawful

importation guideline, including its tax-loss calculation, would

be displaced. Thus, he appears to be suggesting that the reason

that the unlawful importation guideline has no cross-reference to

the fraud guideline is because the offense of unlawful importation

cannot trigger that guideline.

The unlawful importation guideline, however, does

cross-reference the misbranding guideline in cases, like Shafa's,

in which the imported "contraband" is a misbranded drug. And the

misbranding guideline in turn triggers the fraud guideline in cases

"involv[ing] fraud."7 We therefore do not see how the fact that

Shafa makes no argument that, even setting aside which 7

offense constitutes the "instant offense of conviction" under the acquitted-conduct amendment, the misbranding guideline itself permits only consideration of his conduct in committing the offense of misdemeanor misbranding -- and so not his conduct in committing

- 39 - there is no cross-reference to the fraud guideline in the unlawful

importation guideline shows that only misdemeanor

misbranding -- and not unlawful importation -- could be "the

instant offense of conviction" in Shafa's case. A determination

that unlawful importation is "the instant offense of conviction"

in his case would not require the conclusion that the offense of

unlawful importation always triggers the fraud guideline.

For all these reasons, we agree with the government that

Shafa has failed to show that the offense of misdemeanor

misbranding -- and only that offense -- is "the instant offense of

conviction" in his case. Thus, insofar as Shafa's challenge to

the District Court's application of the fraud guideline to him

depends on only the offense of misdemeanor misbranding being "the

instant offense of conviction," the challenge fails.

Shafa does have a fallback argument. Here, he contends

that even if -- as the government contends -- the offense of

unlawful importation is "the instant offense of conviction" in his

case, the acquitted conduct amendment still bars application of

the fraud guideline to him. He argues that this is so because the

conduct that "involved fraud" on which the District Court relied

in applying the fraud guideline to him was conduct for which he

the offense of unlawful importation -- in determining whether "the offense involved fraud."

- 40 - was acquitted when he was acquitted of conspiracy to defraud the

United States and felony misbranding. And, he further contends,

there is no more basis in the record for finding that his conduct

in that regard "establishes, in whole or in part" the offense of

unlawful importation than there is for finding that his conduct in

that regard "establishes in whole or in part" the offense of

misdemeanor misbranding.

The government responds based on what it contends was

the District Court's rationale for applying the fraud guideline to

Shafa. It contends that the District Court "reasoned" that "the

only way Shafa was shown to have imported the implants" was

"through the use of false Customs declarations" and thus that it

found that "the jury in finding the importations also found the

fraud." (Emphasis added.) Thus, the government argues, because

the District Court did not clearly err in so finding, it

supportably found that Shafa's conduct that "involved

fraud" -- using false customs declarations -- "establishes in whole

or in part" the offense of unlawful importation.

To support the assertion that the District Court based

its application of the fraud guideline to Shafa on this line of

reasoning, the government points in part to a statement that the

District Court made in a docket entry concerning Shafa's sentence.

There, the District Court stated:

- 41 - "After presiding over the entirety of the Defendant's trial, and for the reasons stated on the record at the Part I hearing, the [District Court] finds by a preponderance of the evidence that Dr. Shafa engaged in fraudulent conduct that establishes, in whole or in part, the instant offenses of his conviction."

In that statement, however, the District Court does not

purport to assert that, in finding Shafa guilty of unlawful

importation, the jury found that he used false customs

declarations. Nor does the District Court purport to find in

making that statement that Shafa's use of false customs

declarations was "the only way" that the jury could have found

that Shafa was guilty of unlawful importation.

The government also relies on a statement that the

District Court made at the sentencing hearing itself. There, it

stated that: "[W]here the elements of any of the offenses, how the

misbranding, the secretive emails, the . . . way they were

transported that the continuous contact between all of that, how

is that not fraud?"

But, again, the statement does not purport to address

what the jury had to have found in finding Shafa guilty of the

offense of unlawful importation. Nor does this statement make

clear that the District Court was focused on Shafa's conduct in

committing that offense, let alone on his use of false customs

declarations in committing it.

- 42 - To be sure, the District Court continued at the

sentencing hearing by asking: "[H]ow is the mislabeling, the false

attempt to get something in, not as it was but as . . . they

thought it would get through, how is that not fraudulent,

deceptive, false information?" But, here too, the District Court

does not purport to be finding what the jury found when it rendered

its guilty verdicts on the counts charging Shafa with the offense

of unlawful importation. And that is significant because we do

not see how, on this record, the District Court would be compelled

to find that the "only way" that the jury could have found Shafa

guilty of unlawful importation was through his use of false customs

declarations.

After all, to prove that Shafa was guilty of the offense

of unlawful importation, the government could prove either

(1) that Shafa knowingly imported merchandise, and knew the

importation was "contrary to law" or (2) that he received,

concealed, bought, sold or facilitated the transportation,

concealment, or sale of unlawfully imported merchandise where the

importation was imported contrary to law, and the defendant knew

the importation was contrary to law. 18 U.S.C. § 545.

Additionally, the District Court instructed the jury that the

alleged importation that grounded each of Shafa's counts of

unlawful importation could have been "contrary to law" either

because it was done in violation of 18 U.S.C. § 541, which

- 43 - criminalizes the entry of falsely classified goods, or because it

was done in violation of 21 U.S.C. § 331, which makes the delivery

or receipt of a misbranded drug into interstate commerce unlawful.

And, notably, under § 331, the importation would have been contrary

to law simply because the imported merchandise lacked (1) the name

or place of the business, (2) adequate directions for use, or

(3) an "Rx only" symbol.

Moreover, the jury heard evidence at Shafa's trial that

the merchandise at issue lacked both an "Rx only" symbol and a

label indicating the required information. And, in its closing

arguments, the government expressly posited that if the drugs at

issue were "misbranded" by way of "any of the three reasons," the

importation would "have violated the law."8

So, given that there was no special verdict form to

indicate whether the jury found that Shafa had engaged in unlawful

importation because the importations were "contrary to law" under

§ 541 or § 331, we fail to see how the record compels the

conclusion that, as the government posits, "the only way" that the

jury could have found Shafa guilty of the offense of "unlawful

8 The government does not argue that proving misdemeanor misbranding requires proving fraud as an element. Additionally, no one contends that international money laundering was the instant offense of conviction and that the conduct that involved fraud was necessary to establish the elements of international money laundering.

- 44 - importation" was by finding that he used false customs

declarations. The record could supportably permit a finding that

he committed that offense through a different means.

It is possible that the government means to suggest that

even if Shafa's use of false customs declarations was not the "only

way" that the jury could have found him guilty of unlawful

importation, his conduct in that regard still "establishes[] in

whole or in part" that offense. But, if so, the government does

not explain how that could be.

As Shafa points out, courts have interpreted the

Guidelines' use of the word "establish" in the context of another

guideline that uses that word -- § 2B1.1(c)(3) -- to direct courts

applying that guideline to ensure that the conduct in question

satisfies the elements of that offense. See, e.g., United States

v. Griego, 837 F.3d 520, 522 (5th Cir. 2016) (noting the

cross-reference at issue, which used the word "establishes," is

applicable "only if the facts alleged in the indictment establish

the elements of another offense for which the other guideline is

applicable" (emphasis added) (referencing U.S. Sent'g Guidelines

Manual § 2B1.1(c)(3) (U.S. Sent'g Comm'n 2024) ("[T]he conduct set

forth in the count of conviction establishes an offense

specifically covered by another guideline in Chapter

Two . . . ."))). And, while in those cases courts were addressing

an argument that the conduct at issue did not suffice to establish

- 45 - the elements of the offense, we do not see how they can be read to

support the conclusion that the word "establishes" sweeps up

conduct that would not prove any element of an offense and is

merely conduct that is "relevant conduct" for purposes of § 1B1.3.

As Shafa points out, the Sentencing Commission, in

adopting the acquitted-conduct amendment, explained that the "use

of acquitted conduct to increase a defendant's sentence has been

a persistent concern." Notice of Submission to Congress of

Amendments to the Sentencing Guidelines, 89 Fed. Reg. 36853, 36855

(May 3, 2024). The Sentencing Commission thus adopted the

amendment to "exclude acquitted conduct from the scope of relevant

conduct used in calculating a sentence range." Id.

True, the commentary to the acquitted-conduct amendment

makes clear that the amendment does not adopt a bright-line rule

distinguishing "convicted conduct" from "acquitted conduct"

precisely "[t]o ensure that courts may continue to appropriately

sentence defendants for conduct that establishes counts of

conviction." Id. And the commentary also notes that in "cases in

which certain conduct underlies both an acquitted charge and the

instant offense of conviction," the "court is in the best position

to determine whether such overlapping conduct establishes, in

whole or in part, the instant offense of conviction and therefore

qualifies as relevant conduct." U.S. Sent'g Guidelines Manual

§ 1B1.3 cmt. n.10 (U.S. Sent'g Comm'n 2024).

- 46 - We read these passages, though, to show only that the

Sentencing Commission intended to give the sentencing court leeway

to make the on-the-ground assessment of whether the conduct being

relied on in applying a guideline is conduct for which the

defendant had been acquitted in federal court. We do not

understand those passages to bear on the proper construction of

the word "establishes" in the acquitted-conduct amendment.9

9 At oral argument, Shafa did seem to urge us to adopt the categorical approach in applying the acquitted-conduct amendment, such that the defendant's conduct in committing an offense is irrelevant to the inquiry into whether that conduct "establishes, in whole or in part, the instant offense of conviction" and all that matters to the inquiry is what conduct constitutes the "least culpable conduct" necessary to commit the offense. Cf. Boulanger v. United States, 978 F.3d 24, 28-29 (1st Cir. 2020) ("We do not look at the facts of [the defendant's] actual crimes but presume that he engaged in 'the least culpable conduct for which there is a realistic probability of a conviction under the statute.'" (quoting United States v. Baez-Martinez, 950 F.3d 119, 124 (1st Cir. 2020))). The government responded that the use of the word "establishes" in the acquitted-conduct amendment does not require the application of the categorical approach, and we are doubtful that it does. But, because Shafa failed to raise or develop any supporting argument for the use of that approach in his opening brief, we need not resolve the question here. United States v. Pizarro-Berrios, 448 F.3d 1, 5-6 (1st Cir. 2006) ("We have consistently held that, except in extraordinary circumstances, arguments not raised in a party's initial brief and instead raised for the first time at oral argument are considered waived." (citing Piazza v. Aponte Roque, 909 F.2d 35, 37 (1st Cir. 1990))). Instead, we need address only the argument that we understand Shafa to have advanced in his opening brief, which is that the government is wrong to argue either that "the only way" for the District Court to find that Shafa committed unlawful importation based on what the record shows his conduct was in committing that offense was through the use of false customs declarations, or that the District Court made a finding that the jury in fact found as much in finding him guilty of the offense of unlawful importation.

- 47 - 3.

Of course, as even Shafa acknowledges, the

acquitted-conduct amendment only applies as a bar to what the

District Court did in his case if the District Court in fact

applied the fraud guideline based on conduct for which Shafa was

charged and acquitted by a federal court. See id. § 1B1.3(c).

And the government does assert that Shafa's acquittal on the

conspiracy counts could have been based solely on an absence of

evidence of an "agreement" to conspire -- and so not an absence of

evidence that Shafa engaged in the object of the conspiracy, which

was unlawful importation of misbranded drugs.

In making this seeming contention about why the

acquitted-conduct amendment does not apply in Shafa's case,

however, the government does not address an independent argument

that Shafa advances as to why he was acquitted of the conduct on

which the District Court relied in applying the fraud guideline to

him. Specifically, he contends that he was acquitted of that

conduct when he was acquitted of felony misbranding. Thus, the

government's assertion about the import of Shafa's acquittal on

the conspiracy charges fails to amount to an argument that the

District Court relied solely on conduct for which Shafa had not

been acquitted in federal court.

It is notable, too, that the government does not ask

us -- at least in any clear way -- to affirm the application of

- 48 - the fraud guideline to Shafa on the ground that the

acquitted-conduct amendment simply does not apply in Shafa's case

because the District Court relied solely on conduct for which he

had not been charged federally (and, therefore, conduct of which

he had not been not acquitted by a federal court). Instead, the

government chiefly focuses on a distinct argument. It argues that

the acquitted-conduct amendment is no bar here because, even though

the conduct on which the District Court relied in applying the

fraud guideline to Shafa was conduct of which he was acquitted in

federal court, it still was conduct that "establishes, in whole or

in part," the offense of unlawful importation.

That said, as we will explain in more detail below, it

does appear that the District Court relied on some conduct for

which Shafa had not been charged at all -- and so conduct of which

he had not been acquitted in federal court -- to calculate the

amount his offense level had to be increased under the fraud

guideline. Specifically, the District Court appears to have relied

on some of Shafa's uncharged conduct in determining both the

magnitude of the "loss" under the fraud guideline and the number

of victims in his case.

Nonetheless, the District Court does not appear to have

based the magnitude of the loss solely on that uncharged conduct.

In addition, the District Court did not directly address whether

the conduct that it determined "involved fraud" was only conduct

- 49 - for which Shafa had not been charged and acquitted when he was

acquitted of conspiracy to defraud the United States and felony

misbranding. Nor can we discern any implicit finding on that score

one way or the other.

We thus do not think it prudent to affirm the application

of the fraud guideline in Shafa's case based solely on the

uncharged conduct on which the District Court appeared to rely in

determining how much to increase Shafa's offense level pursuant to

the fraud guideline. And, we emphasize, the government does not

ask us to do so.

4.

Where, then, does our analysis up to this point leave

us? Simply put, there are a number of ambiguities about the

precise basis on which the District Court determined that the fraud

guideline applied to Shafa. And those ambiguities appear to

implicate the question of whether the acquitted-conduct amendment

bars the application of that guideline to him. As a result, we

cannot, at this stage of the proceedings, resolve whether the

District Court erred in applying the fraud guideline to Shafa.

Accordingly, we retain jurisdiction over this appeal and remand so

that the District Court may clarify the basis for its ruling as to

why the fraud guideline applied.

Specifically, on remand, the District Court is directed

to explain whether it agrees with the government's contention that

- 50 - the conduct that it determined "involved fraud" was Shafa's conduct

in submitting false customs declarations. If the District Court

does not agree, then the District Court is further directed to

identify the conduct that it found that Shafa had engaged in that

"involved fraud" and the basis in the record for finding that he

engaged in that conduct.

Next, the District Court is directed to explain whether

Shafa had been acquitted of the conduct that it identifies as the

conduct that Shafa had engaged in that "involved fraud" when he

was acquitted of felony misbranding and conspiracy to defraud the

United States. In doing so, the District Court is directed to

explain why it concludes that he either was or was not acquitted

of that conduct by virtue of those acquittals.

Finally, if the District Court determines that, by

virtue of either of those acquittals, Shafa had been acquitted of

the conduct that it identifies is the conduct that he had engaged

in that "involved fraud," then it is further directed to identify,

for purposes of applying the acquitted-conduct amendment, the

"instant offense of conviction" in Shafa's case. And, after having

done so, it is then directed to explain its basis for finding that,

on this record, that conduct "establishes, in whole or in part,

the instant offense of conviction."

In doing so, the District Court must keep in mind that

we reject the government's suggestion, insofar as the government

- 51 - means to make it, that the word "establishes" in the

acquitted-conduct amendment means to sweep up all "relevant

conduct." And, the District Court also must keep in mind our

reasons for concluding that this record does not compel a finding

that the "only way" that a jury could find that Shafa was guilty

of the counts charging him with unlawful importation was through

his use of false customs declarations.

Notwithstanding that we must remand for a determination

of whether and why the fraud guideline applies in Shafa's case, we

think it sensible to address Shafa's other challenges to his

sentences. After all, depending on what happens on remand, the

resolution of those challenges still may be relevant. We therefore

see no reason not to address them now.

The first of these other challenges concerns how the

District Court calculated the loss amount under the fraud

guideline. We review a court's loss calculation for clear error

but review its definition of loss de novo. See United States v.

Ihenacho, 716 F.3d 266, 276 (1st Cir. 2013). Shafa identifies two

problems with the District Court's loss calculation, but neither

ground for finding error holds up on review.

First, Shafa emphasizes that the offenses of conviction

date back to June 2016 at the earliest. For that reason, he

- 52 - contends, the District Court erred under the acquitted-conduct

amendment in calculating the loss amount by relying on conduct

dating back to the alleged start date of the charged conspiracy,

which was 2008. That is so, Shafa contends, because Shafa was

acquitted of the conspiracy counts. He therefore contends that

the District Court erred in increasing his offense level by 12.

The government argues, however, that in calculating the

loss amount, the District Court made an "implicit finding" that

there were "uncharged shipments," which "were sufficiently tied to

his convictions for" unlawful importation. We agree.

The District Court pointed to "the testimony of Agent

Roy," who stated that the investigation began in 2008, in support

of the finding that "the time period alleged in the indictment for

the offenses of conviction" -- and so not just for the conspiracy

offenses of which Shafa was acquitted -- was January 2008 through

January 2018. During his testimony, Agent Roy read from a 2009

email between Moran and Shafa in which Moran asked Shafa whether

Shafa wanted him "to send by courier again" and noted that he had

not shipped to the United States "since the last time that

[Shafa's] shipment was held up." In addition, the District Court

stated on the record that the referenced 2009 email was "clearly

not the first communication between" the pair. Thus, it was not

clear error for the District Court to consider additional uncharged

shipments in sentencing Shafa. See United States v. Eisom, 585

- 53 - F.3d 552, 557 (1st Cir. 2009) ("[U]ncharged conduct is relevant if

the government proves by a preponderance of the evidence that such

uncharged conduct is part of the same course of conduct or common

scheme or plan as the charged conduct.").

The Government also points out that if Shafa means to be

arguing that the acquitted-conduct amendment precludes even this

uncharged conduct from being deemed relevant conduct, the

amendment's text is directly to the contrary. See U.S. Sent'g

Guidelines Manual § 1B1.3(c) (U.S. Sent'g Comm'n 2024) ("Relevant

conduct does not include conduct for which the defendant was

criminally charged and acquitted in federal court . . . ."

(emphasis added)). Shafa offers no response to that seemingly

insurmountable obstacle.

Second, Shafa takes issue with the evidentiary basis for

the District Court's finding that the loss exceeded $250,000 and

thus that, under the fraud guideline's loss table, a 12-level

increase to his offense level was required. The District Court

found that the loss was of that magnitude based on the amounts

Shafa's patients paid for the treatment involving the misbranded

drugs that they received.

Shafa contends the District Court erred because the

record shows, by a preponderance, that his patients benefitted

from the treatment for which they paid. But our caselaw is to the

contrary when the good or service involved is unlawful. See United

- 54 - States v. Gonzalez-Alvarez, 277 F.3d 73, 80 (1st Cir. 2002) ("Where

a product has a value of zero as a matter of law, but consumers

pay for the product as if it had value, the buyers have been robbed

of the benefit of their bargain."); United States v. Kumar, 112

F.4th 30, 36 (1st Cir. 2024) (explaining that the loss amount under

the loss table in § 2B1.1(b)(1) "is essentially equal to the value

paid by customers for the pills that [the defendant] conspired to

import"); cf. § 2B1.1 cmt. n.3(E)(v) (providing that "[i]n a case

involving a scheme in which . . . goods for which regulatory

approval by a government agency was required but not obtained, or

was obtained by fraud, loss shall include the amount paid for" the

item at issue "with no credit provided for the value of [that]

item[]").

Shafa separately challenges the way that the District

Court applied the enhancement for ten or more victims that is set

forth in § 2B1.1(b)(2)(A)(i). He does so on two grounds, neither

of which has merit.

First, Shafa argues that the list of the ten individuals

that the government identified as victims included one individual

who testified to having implants that worked as expected. In fact,

however, the government put forth evidence that all ten victims

suffered medical complications from the implants, including the

witness that, as Shafa correctly observed, also testified to having

- 55 - an implant that worked as expected. See U.S. Sent'g Guidelines

Manual § 2B1.1 cmt. n.1 (U.S. Sent'g Comm'n 2024) (defining a

victim as, among other options, "any individual who sustained

bodily injury as a result of the offense"). So, this contention

fails.

Second, Shafa argues that four of the individuals

identified by the government as victims were treated "outside the

time period covered by Shafa's offenses of conviction and therefore

should have been excluded under the acquitted-conduct amendment."

Here, again, he asserts that we must reach that conclusion because

the period covered by the convictions starts in 2016. However, as

discussed above, the District Court did not err in finding that

the course of conduct that included the "offenses of conviction"

dated back to 2008. Therefore, the treatments -- the earliest of

which was in 2011 for patient "MT" -- were well within the period

for the offenses of conviction as determined by the District Court.

Accordingly, it is of no consequence that, extending as far back

as 2011, four of the identified victims were treated prior to 2016.

VIII.

We have one loose end to tie up. It concerns only the

sentence that he received for his misdemeanor misbranding

conviction. In the course of advancing his challenge to the

District Court's decision to apply the fraud guideline to him,

Shafa points out that the statutory maximum for a conviction for

- 56 - the offense of misdemeanor misbranding is one year. See 21 U.S.C

§ 333(a)(1). And it does appear that the District Court imposed

a sentence to be served concurrently for misdemeanor misbranding

that is greater than one year.

The government concedes that the District Court should

have imposed a sentence of 12 months for the misdemeanor

misbranding conviction, to run concurrently with the sentences

imposed for the other convictions, which were not subject to a

statutory maximum that is relevant here. We therefore vacate the

sentence imposed for the conviction of misdemeanor misbranding.10

IX.

For the foregoing reasons, we affirm Shafa's

convictions, while vacating the sentence for the conviction on

Shafa further points out that "[e]ven where (as here) there 10

are multiple offenses of conviction, 'where a statutorily authorized maximum sentence on a particular count is less than the minimum of the applicable guideline range, the sentence imposed on that count shall not be greater than the statutorily authorized maximum sentence on that count'" (emphasis added) (citing U.S. Sent'g Guidelines Manual § 5G1.2 n.3(B) (U.S. Sent'g Comm'n 2024)). It is unclear whether he makes this observation to support his contention that the "instant offense of conviction" in his case is misdemeanor misbranding rather than unlawful importation or to suggest that the statutory maximum for unlawful importation in his case cannot be greater than the one-year statutory maximum for misdemeanor misbranding, given that the recommended guidelines sentencing range of unlawful importation in his case is greater than one-year in part because the fraud guideline applies to him through the misdemeanor misbranding guideline. Either way, though, we do not see how the portion of the Guidelines Manual that he invokes is of any relevance. And that is because the offense of unlawful importation is not subject to a one-year statutory maximum.

- 57 - misdemeanor misbranding. We retain jurisdiction over this appeal

and remand for further consideration consistent with this

decision.

- 58 -