United States v. Carrasco

• Court: Court of Appeals for the First Circuit
• Decided: August 28, 2023
• Docket: 21-1396
• Status: Published

Opinion

United States Court of Appeals For the First Circuit

No. 21-1396

UNITED STATES,

Appellee,

v.

ALEJANDRO CARRASCO,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF PUERTO RICO

[Hon. Francisco A. Besosa, U.S. District Judge]

Before

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

Rachel Brill for appellant. Nicole R. Lockhart, Trial Attorney, with whom Kenneth A. Polite, Assistant Attorney General, Lisa H. Miller, Deputy Assistant Attorney General, Corey R. Amundson, Chief, Public Integrity Section, and James I. Pearce, Attorney, Appellate Section, were on brief, for appellee.

August 28, 2023 BARRON, Chief Judge. Alejandro Carrasco Castillo

("Carrasco") appeals his convictions and sentence for violating 18

U.S.C. § 666. The underlying charges stem from his role in the

allegedly corrupt awarding of contracts by various Puerto Rico

municipalities. We affirm.

I.

More than a decade ago, federal authorities began

investigating allegations that three Puerto Rico municipalities

had corruptly awarded contracts to a company owned by Juan Carlos

Mercado, who at the time was a contractor and environmental

engineer. Federal authorities arrested Mercado in February 2012

in connection with the investigation, and he agreed to cooperate

with them by recording his conversations with Eduardo

Rivera-Correa, who was the mayor of one of the municipalities, and

Carrasco, an attorney retained by each of the three municipalities

to provide legal representation.1

Thereafter, on July 8, 2014, Carrasco was indicted in

the United States District Court for the District of Puerto Rico

on four counts of violating 18 U.S.C. § 666(a)(1)(B).2 Section

666(a)(1)(B) provides in relevant part:

1 The criminal complaint against Mercado was dismissed without prejudice in December 2012 pending Mercado's completion of an eighteen-month pretrial diversion program. The same indictment also charged Rivera-Correa with various 2

offenses related to the alleged scheme.

- 2 - [w]hoever . . . being an agent of an organization, or of a State, local, or Indian tribal government, or any agency thereof . . . corruptly solicits or demands for the benefit of any person, or accepts or agrees to accept, anything of value from any person, intending to be influenced or rewarded in connection with any business, transaction, or series of transactions of such organization, government, or agency involving any thing of value of $5,000 or more . . . shall be fined under this title, imprisoned not more than 10 years, or both.3

Each count alleges that, in violation of § 666, Carrasco

took payments from Mercado in connection with the award of

contracts to Mercado's environmental consulting firm by one of the

three Puerto Rican municipalities that had retained Carrasco. The

first count alleges that Carrasco received payments from July 2009

through August 2009 in connection with contracts awarded by the

municipality of Barceloneta. The second count alleges that he

received payments from March 2010 to July 2010 in connection with

contracts awarded by the municipality of Rio Grande. The third

count alleges that he received payments from August 2010 through

October 2010 in connection with contracts awarded by the

The provisions of 18 U.S.C. § 666(a) apply only "if the 3

circumstance described in subsection (b) of [18 U.S.C. § 666] exists." Subsection (b) provides that "[t]he circumstance referred to in subsection (a) of this section is that the organization, government, or agency receives, in any one year period, benefits in excess of $10,000 under a Federal program involving a grant, contract, subsidy, loan, guarantee, insurance, or other form of Federal assistance." Carrasco accepts that each of the three municipalities met this condition in the relevant years.

- 3 - municipality of Juncos. The fourth count alleges that he received

payments in July 2011 in connection with contracts awarded by,

once again, Barceloneta.

Carrasco was tried on the charges before a jury in

December 2019 and was found guilty on all four counts. A judgment

of conviction was entered, and the District Court sentenced him on

April 27, 2021, to 120 months of imprisonment and 3 years of

supervised release. Carrasco then timely filed this appeal.

II.

Carrasco first seeks the reversal of his convictions on

the ground that they are not supported by sufficient evidence. To

succeed, he must show that the evidence in the record does not

suffice to permit a rational juror to find him guilty beyond a

reasonable doubt of violating § 666. See United States v. Levin,

13 F.4th 96, 99-100 (1st Cir. 2021). Our review is de novo, but

we "review[] the evidence, and mak[e] all inferences and

credibility choices, in the government's favor." United States v.

Rodríguez-Torres, 939 F.3d 16, 23 (1st Cir. 2019).

A.

Carrasco directs our attention initially to what the

record shows with respect to the element of the offense --- set

forth in § 666(a)(1) -- that requires the government to prove

beyond a reasonable doubt that he was an "agent of a[] . . . local

. . . government." Section 666(d)(1) defines an "agent" of a local

- 4 - government to be "a person authorized to act on behalf of" it and

specifies that the definition of the term "includes a servant or

employee, and a partner, director, officer, manager, and

representative."

To prove that Carrasco was such an "agent," the

government submitted into evidence his contracts with Barceloneta,

Rio Grande, and Juncos. Carrasco does not dispute that the text

of each of the contracts authorized him to provide legal

representation to the named municipality "in the Courts of Puerto

Rico" and "the administrative and investigative agencies."

Therefore, it would appear that the evidence does suffice to

support the "agent" element of the offense, as each of the

contracts would appear to show that he was "authorized to act on

behalf of" the relevant municipality and so that he was an "agent"

of that municipality. See Representative, Black's Law Dictionary

(11th ed. 2019) (defining "representative" as "[s]omeone who

stands for or acts on behalf of another").4

Carrasco nonetheless contends that the evidence does not

suffice to satisfy the "agent" element because no evidence in the

4Carrasco does point to our prior statement that "there is no more classic government 'representative' than a legislative branch officer," United States v. Fernandez, 722 F.3d 1, 8 (1st Cir. 2013), to argue that he cannot be an "agent" of the municipalities solely because the contracts make him a "representative" of the municipalities. But, our conclusion that Carrasco is an "agent" for purposes of § 666(d)(1) relies on the

- 5 - record suffices to show that he took any specific action under any

of the contracts on behalf of any of the municipalities. But the

text of § 666(d)(1) does not support a construction of the statute

that would require the government to make that showing to satisfy

the "agent" element.

By its plain terms, the text of the statute defines an

"agent" to be merely "a person authorized to act on behalf

of . . . a government." 18 U.S.C. § 666(d)(1) (emphasis added).

It does not define an "agent" to be only a person who "acts" on

behalf of a government.

Nor is there any reason to conclude from the text of

related provisions that the words "authorized to act" in

§ 666(d)(1) mean "acts," such that it is not enough to prove that

the person has been merely authorized to act. After all, a

separate provision of § 666(d)(1) states that a "person" qualifies

as an "agent" if that person is a "representative." Id. Thus,

that provision does not state that a "person" so qualifies even if

they have only been "authorized to be a . . . representative."

Reinforcing the conclusion that the words "authorized to

act" mean what they say is the fact that the Supreme Court of the

United States has explained in construing other parts of § 666

term "represent" as used in the contracts, not on the term "representative" as used in § 666(d)(1). We thus need not address Carrasco's contention that Fernandez would preclude us from relying on that term.

- 6 - that the statute's "expansive" and "unqualified language," Salinas

v. United States, 522 U.S. 52, 56 (1997), "reveals Congress'

expansive, unambiguous intent to ensure the integrity of

organizations participating in federal assistance programs,"

Fischer v. United States, 529 U.S. 667, 678 (2000). In addition,

both our Circuit and the Supreme Court have "repeatedly rejected

constructions of § 666 that would impose limits beyond those set

out in the plain meaning of the statute."5 United States v.

Fernandez, 722 F.3d 1, 10 (1st Cir. 2013); see also Fischer, 529

U.S. at 678.

Carrasco contends that a prior precedent of ours, United

States v. Sotomayor-Vázquez, 249 F.3d 1 (1st Cir. 2001), as well

as two precedents from other circuits, United States v. Lupton,

620 F.3d 790, 800-01 (7th Cir. 2010); United States v. Hudson, 491

F.3d 590, 594-95 (6th Cir. 2007), support his position. We

disagree.

Sotomayor-Vázquez did hold that evidence in the record

in that case showed that the defendant was an "agent" of the

non-profit entity at issue because, although the defendant was

formally an independent contractor, the defendant "acted as [the]

5 Carrasco's contention that the government was required to show a nexus between the matters on which Carrasco was authorized to act on behalf of the municipalities and the contracts that he was alleged to have helped Mercado obtain fails for the same reason: Carrasco does not identify, nor can we discern, any textual basis for such a limitation on the reach of § 666(d)(1).

- 7 - executive director" of the entity by approving all its

organizational decisions, meeting with city officials on the

agency's behalf, and making decisions regarding hiring and firing.

249 F.3d at 8-9. But we made clear in so holding that the

definition of "agent" under § 666(d)(1) has two "aspect[s]": one

relating to a person's having been "authorized to act on behalf

of" the covered entity and the other relating to whether the person

was an "employee, partner, director, officer, manager, or

representative" of that entity. Id. at 8. We also made clear

that we based our holding only on that second "aspect of the

statutory definition." Id. Thus, our decision there in no way

indicates either that an "agent" is not merely a person who was

"authorized to act on behalf of" the relevant entity or that

evidence that suffices to show only that the defendant was so

authorized cannot suffice to show that the person qualifies as an

"agent."

Lupton also is no help to Carrasco. The evidence there

was deemed sufficient to render the defendant an "agent" based on

the activities of the defendant vis-à-vis a state agency. 620

F.3d at 800-01. But the contract between the real estate firm

that employed the defendant in that case and the state of Wisconsin

expressly provided that the firm was acting as "an independent

contractor and not as an officer, employee, or agent of the state."

Id. at 800. Thus, while the court in Lupton looked beyond the

- 8 - terms of the contract to determine that the defendant was an

"agent" for purposes of § 666, the court did not thereby suggest

that contracts like those at issue in Carrasco's case are

inadequate on their own to supportably show that a defendant is an

"agent" of a local government.

Finally, in Hudson, the Sixth Circuit determined that

the evidence sufficed to satisfy the "agent" element based on both

contract terms that "gave [the defendant] broad authority to set

up a television station in the high school" and testimony that the

defendant exercised that authority. 491 F.3d at 594-95. But,

once again, nothing in that case suggests that a contract's terms,

standing alone, are insufficient to support a jury's finding that

a defendant was an "agent" in the relevant sense when those terms

authorize the defendant to act on behalf of the relevant entity.

Carrasco does also argue that he is similarly situated

to the defendant in United States v. Pinson, 860 F.3d 152 (4th

Cir. 2017). There, the defendant was convicted of aiding and

abetting -- in violation of § 666 -- theft carried out by an

employee of a company that had been hired by a county in South

Carolina. Id. The Fourth Circuit concluded that the employee was

not an "agent" under § 666(d)(1) because of the limited nature of

the tasks that he performed for his employer. Id. at 165-66. As

the court explained, the employee "had no actual or implied

authority to act on [the county's] behalf in any capacity." Id.

- 9 - at 166. Rather, because the employee's only relevant duty was

"receiving and packaging invoices from the company's contractors

and submitting them to [the county] for payment," the employee

"acted solely on behalf of the" corporate entity, not the county.

Id. at 165.

Carrasco contends that, for all the record shows in his

case, he could have been tasked with carrying out only the same

sort of limited tasks that were determined to be insufficient in

Pinson to permit the employee there to be deemed an agent under

§ 666. Carrasco thus contends that the contracts alone cannot

suffice to permit a factfinder to find that he was an "agent" under

§ 666.

But, while the Fourth Circuit's conclusion in Pinson

hinged on the evidence presented to show the employee's

relationship with the county, there is no suggestion in Pinson

that any evidence was presented to show that, notwithstanding the

employee's actual duties, the employee was formally authorized to

act on the county's behalf. In Carrasco's case, by contrast, a

rational jury could conclude based on the contracts between him

and the municipalities that he was authorized to act on behalf of

those municipalities, given the express authorization in each

contract for him to "represent" the relevant municipality. We

thus do not see how Pinson supports Carrasco's position any more

than the other readily distinguishable precedents on which he

- 10 - relies and so reject his sufficiency challenge insofar as it takes

aim at the record support for the "agent" element of the offense

that underlies his convictions.

B.

Carrasco's other ground for challenging his § 666

convictions on sufficiency grounds is that the government failed

to supportably show that he engaged in any "official act." Here,

he contends that the government was required to prove that he

received funds in exchange for taking "an official act" to prove

that he violated § 666. He then goes on to contend that we must

apply the definition of "official act" that the Supreme Court set

forth in construing the "official act" element of 18 U.S.C.

§ 201(a)(3) in McDonnell v. United States, 579 U.S. 550 (2016),

and that there is no evidence in the record that could suffice to

show that he received the funds from Mercado in exchange for taking

such an "official act."

The Court explained in McDonnell that an "official act"

occurs when a "public official . . . make[s]" (or agrees to make)

"a decision or take[s]" (or agrees to take) "an action on [a]

'question, matter, cause, suit, proceeding, or controversy.'" 579

U.S. at 574 (quoting 18 U.S.C. § 201(a)(3)). The Court further

explained that § 201(a)(3) required that the "question, matter,

cause, suit, proceeding or controversy," § 201(a)(3), must be one

which is, or which may at a future time be, "pending" before the

- 11 - official. 579 U.S. at 570 (quoting 18 U.S.C. § 201(a)(3)). The

Court also explained that an "official act" occurs for purposes of

§ 201 when a public official "us[es] his official position to exert

pressure on another official to perform an 'official act,' or to

advise another official, knowing or intending that such advice

will form the basis for an 'official act' by another official."

Id. at 574.

The necessary premise of this ground of Carrasco's

sufficiency challenge is that § 666 has an "official act" element.

But the text of § 666, unlike the text of § 201 that the Supreme

Court construed in McDonnell, does not include the phrase "official

act." And, as the government points out, several circuits have

held that the government need not show that a defendant engaged in

an "official act" to secure a conviction under § 666. See United

States v. Lindberg, 39 F.4th 151, 165-169 (4th Cir. 2022); United

States v. Roberson, 998 F.3d 1237, 1246-47 (11th Cir. 2021); United

States v. Ng Lap Seng, 934 F.3d 110, 131-34 (2d Cir. 2019); United

States v. Porter, 886 F.3d 562, 565-66 (6th Cir. 2018).

Moreover, although our Circuit has proceeded in some

cases on the understanding that § 666 does contain an "official

act" element, we have done so only in cases in which the government

did not dispute the point and in which the jury had been instructed

that the offense does contain an "official act" element, see, e.g.,

- 12 - United States v. Martínez, 994 F.3d 1, 6-7 (1st Cir. 2021). We

thus have not held that § 666 does have an "official act" element.

Against this precedential backdrop, it is potentially

significant both that the District Court did not instruct the jury

in Carrasco's case that § 666 has an "official act" element6 and

that in this case the government contests whether § 666 has such

an element. But we need not decide whether § 666 has the element

in question because Carrasco has failed to show that the government

did not present sufficient evidence for a rational juror to

conclude that element was met.

The record supportably shows that Carrasco agreed to

"advise" the mayors of the relevant municipalities "knowing or

intending that such advice w[ould] form the basis for an 'official

act'" by those municipal officials -- namely, the awarding of

contracts by those municipalities to a company associated with

Mercado. McDonnell, 579 U.S. at 574. That evidence takes the

form chiefly of testimony from Mercado himself.

Mercado testified that his environmental consulting firm

had contracts with the municipalities of Barceloneta, Juncos, and

Rio Grande. He further testified that the contracts were not

6 Carrasco's briefing does at points assert that "[t]he jury should . . . have been instructed in conjunction with McDonnell's two-part test" and thus instructed to identify an official act taken by Carrasco, but Carrasco's counsel clarified during oral argument that no challenge was being made on appeal to the jury instructions given by the District Court.

- 13 - awarded pursuant to a bidding process but instead after a

negotiation with the municipal government. He then testified that

he made payments to Carrasco in exchange for Carrasco providing

"[a]ccess, protection, watch my back," while explaining that the

basis for his belief in Carrasco's ability to deliver the

agreed-upon "[a]ccess," "protection," and back-watching was

Mercado's belief that Carrasco had "[t]otal access" and held

"[t]otal influence" over the mayors in the three municipalities.

Mercado further testified that he understood Carrasco would, in

exchange for the payments, ensure that Mercado would receive

municipal contracts. And, finally, Mercado testified that he

understood Carrasco to be soliciting these payments by asking for

"loose change" in connection with Mercado's receipt of municipal

contracts.

In addition, the record shows both that the government

submitted into evidence certain checks that Mercado made out to

Carrasco and that Mercado testified that those checks were paid in

connection with the specific contracts identified in the

indictment. So, there is evidence that at least partly

corroborates Mercado's testimony.

Notwithstanding this collection of evidence, Carrasco

contends that the evidence in the record does not suffice to

satisfy the "official act" element. He does so by focusing on

Mercado's description of Carrasco's alleged provision of

- 14 - "[a]ccess, protection," and watching Mercado's back. Carrasco

argues that these services are too "speculative and

nebulously-described" to meet the McDonnell standard for what

constitutes an "official act." Carrasco then contends that the

payments Mercado made to him were not bribes but rather were akin

to the speculative gift-giving at issue in United States v.

Sun-Diamond Growers of California, 526 U.S. 398 (1999), which the

Supreme Court concluded was not in exchange for an "official act."

But Mercado's testimony, as we have explained, provides

a basis for finding more than that Carrasco had provided Mercado

with merely "access" or "protection." It also suffices to permit

a finding that Carrasco "advise[d]" the mayors "knowing or

intending that [his] advice w[ould] form the basis for an 'official

act'" taken by the mayors -- namely, the award of the contracts to

Mercado. McDonnell, 579 U.S. at 574. And because Carrasco makes

no argument as to why such advice would not for that reason qualify

as an "official act," we reject his contention that the evidence

does not suffice under McDonnell to allow a rational jury to

conclude that he had undertaken such an act.

III.

We still must consider Carrasco's two evidentiary

challenges, each of which was preserved below, and each of which

- 15 - he contends supports our vacating his convictions. We reject these

challenges as well.

Carrasco first argues that the District Court erred in

admitting evidence of municipal contracts and related payments

made by Mercado to Carrasco that went beyond the specific contracts

and related payments that ground the specific § 666 charges for

which Carrasco was indicted. The relevant facts are as follows.

Carrasco's indictment charged him with receiving

approximately $72,300 in payments from Mercado related to seven

municipal contracts. The evidence of these payments at trial took

the form of checks that were made out from Mercado to Carrasco.

The memo field on each check stated that the check was paid for

"legal services" or some other seemingly legitimate service that

Carrasco had provided or was to provide to Mercado. But the

government did not submit into evidence only checks from Mercado

to Carrasco that the government contended were payments to Carrasco

in return for influencing the award of the contracts that form the

predicate for the § 666 charges against Carrasco. The government

also submitted into evidence additional checks that Mercado

testified were kickbacks from Mercado to Carrasco in exchange for

- 16 - Carrasco agreeing to steer to Mercado contracts beyond the

contracts mentioned in the indictment.7

Carrasco contends that the District Court erred in

admitting into evidence these additional checks as well as

Mercado's related testimony. In his view, that evidence

constituted propensity evidence of the type prohibited by Federal

Rule of Evidence 404(b).

To make out this contention, Carrasco first argues that

the evidence was not admissible under Rule 404(b) as evidence

"intrinsic" to the conduct for which Carrasco was indicted. He

contends that is so because this evidence was relevant only to

other, uncharged conduct -- that is, the evidence was "extrinsic

to the crime charged." United States v. Gonyer, 761 F.3d 157, 162

(1st Cir. 2014) (quoting United States v. Roszkowski, 700 F.3d 50,

56 (1st Cir. 2012)).

The government responds that even if the evidence

regarding the additional checks is "extrinsic," it is admissible

because it has a "special relevance" under Rule 404(b). United

7 In total, the government submitted into evidence forty-one checks representing approximately $195,000 in payments from Mercado to Carrasco. Mercado testified that three of those checks, totaling $2,989, were for legitimate legal services. It appears that Mercado was not asked to testify as to whether four of the checks, totaling $5,850, were payments for legitimate services provided by Carrasco or payments related to the steering of contracts to Mercado. Mercado testified that the remaining thirty-four checks were payments made in exchange for Carrasco agreeing to steer contracts to Mercado.

- 17 - States v. Henry, 848 F.3d 1, 8 (1st Cir. 2017) (citing United

States v. Hicks, 575 F.3d 130, 142 (1st Cir. 2009)). In

particular, the government argues that the evidence is specially

relevant because it shows not only Carrasco's intent in accepting

the payments for which he was charged but also his modus operandi

for receiving payments in connection with his agreement with

Mercado to influence the mayors to steer contracts to Mercado's

firm in exchange for his receiving payments from Mercado. See id.

(quoting Fed. R. Evid. 404(b)(2)) (noting that "special relevance

under Rule 404(b)" includes "proving motive, opportunity, intent,

preparation, plan, knowledge, identity, absence of mistake, or

lack of accident"). And, notably, Carrasco does not dispute that

the evidence was of this specially relevant sort.

Thus, in the end, Carrasco's challenge boils down to his

contention that this evidence was not admissible because the

evidence was unduly prejudicial and thus violative of Rule 403.

See id. ("If prior crime evidence has special relevance under Rule

404(b), the court must move on to consider whether the evidence

should nevertheless be excluded under Rule 403."). But, as the

party opposing the admission of evidence on Rule 403 grounds,

Carrasco bears the burden of establishing "that the probative

value" of the evidence at issue "is substantially outweighed by

the danger of unfair prejudice." United States v. Tse, 375 F.3d

148, 162 (1st Cir. 2004). And, given that "we afford deference to

- 18 - a [district court]'s balancing decision, and '[o]nly rarely -- and

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. Doe, 741 F.3d 217, 229

(1st Cir. 2013) (alteration in original) (internal quotation

omitted) (quoting United States v. Li, 206 F.3d 78, 84-85 (1st

Cir. 2000)), we conclude that Carrasco has not carried that burden

here.

Carrasco's only argument as to why the admission of the

challenged evidence was unduly prejudicial is that "[f]looding the

jury" with that evidence "about uncharged conduct practically

guaranteed that the jury would be unduly influenced" and thus

unable to disentangle the acceptable non-propensity inference from

the forbidden propensity inference. And Carrasco relies for this

argument solely on United States v. Gilbert, 229 F.3d 15, 21-25

(1st Cir. 2000).

But, in Gilbert, we affirmed, in an interlocutory appeal

brought by the government, a district court's decision to exclude

evidence, id. at 20. Here, by contrast, we are reviewing a

defendant's challenge to a district court's decision to admit

evidence.

Moreover, in affirming the district court's decision not

to admit the evidence in Gilbert, we concluded that the

- 19 - non-propensity purpose of admitting the evidence was of only

marginal relevance to the government's case. Id. at 24. By

contrast, Carrasco's intent in accepting checks with innocuous

explanations in their memo lines -- namely, whether he believed

those checks to be payments for legitimate services or for steering

contracts to Mercado -- was a central issue at trial.

To be sure, we have acknowledged that evidence

admissible for a special purpose under Rule 404(b) may be unfairly

prejudicial when other evidence that carries less risk of being

unduly prejudicial could have been used to prove the fact in

question. See United States v. Varoudakis, 233 F.3d 113, 122 (1st

Cir. 2000). But in Varoudakis, we noted that the record was

replete with compelling, alternative evidence already before the

jury that spoke to the same issue, thereby lessening any probative

value of the proffered "other acts" evidence. Here, by contrast,

the evidence of the additional checks and Mercado's related

testimony were central to establishing Carrasco's intent. And,

although Carrasco claims that the admission of the other checks

and accompanying testimony risked "[f]looding the jury" with

evidence of uncharged bad acts and thus that the jury would make

an improper propensity inference,8 it is unclear how many of the

8To the extent Carrasco challenges the illustrative charts the government used to summarize the evidence of payments, both charged and uncharged, that Mercado made to Carrasco, he has failed

- 20 - checks might have been admitted without creating that risk.

Moreover, we have in similar circumstances found no error in the

admission of repetitive evidence of prior bad acts with special

relevance when "the repetition of the conduct was itself distinctly

probative." United States v. Rodriguez-Estrada, 877 F.2d 153, 156

(1st Cir. 1989); see id. at 155-56 (affirming, in a case where

defendant was charged with twenty counts of embezzlement for

misappropriating twenty weekly expense allowances, the admission

under Rule 404(b) of thirty-one checks the government argued

represented thirty-one identical but uncharged misappropriations

of weekly allowances). We thus conclude that the District Court

did not abuse its discretion in admitting evidence of Mercado's

illicit but uncharged payments to Carrasco.9

to develop the argument and thus has waived it. See United States v. Zannino, 895 F.2d 1, 17 (1st Cir. 1990). 9 Carrasco contends that the District Court erred in failing to give the jury a limiting instruction concerning the purpose for which the jury could consider the evidence of the prior payments he had accepted from Mercado. But Carrasco "may not complain about the absence of a limiting instruction because he never requested one." United States v. Lugo Guerrero, 524 F.3d 5, 14 (1st Cir. 2008) (citing Huddleston v. United States, 485 U.S. 681, 691–92 (1988)) (explaining that Huddleston "not[ed] that Federal Rule of Evidence 105 provides protection from unfair prejudice by requiring the trial court, upon request, to instruct the jury that the evidence of other acts is to be considered only for the proper purpose for which it was admitted"). The District Court therefore "did not err by failing to issue, sua sponte, the limiting instruction that [Carrasco] now claims was essential." Id. (citing United States v. Cartagena–Carrasquillo, 70 F.3d 706, 713 (1st Cir. 1995)) (explaining that Cartagena-Carrasquillo "refus[ed] to impose obligation on court to give, sua sponte, a limiting

- 21 - B.

Carrasco's second evidentiary challenge concerns

portions of Mercado's testimony in which Mercado characterized the

content of certain interactions he recounted and certain recorded

conversations that were played for the jury. Carrasco contends

that Mercado's characterizations of these conversations

contravened Federal Rule of Evidence 701 and so were improperly

admitted into evidence. We need not decide whether that is so,

however, because we agree with the government that any error on

this score was harmless.

The admission of improper testimony is harmless if it is

"highly probable that the error did not influence the verdict."

United States v. Flores-De-Jesus, 569 F.3d 8, 27 (1st Cir. 2009)

(quoting United States v. Casas, 356 F.3d 104, 121 (1st Cir.

2004)). The government bears the burden of making that showing.

See id. (quoting United States v. Rodriguez-Marrero, 390 F.3d 1,

18 (1st Cir. 2004)). To determine whether the government has made

that showing, we must engage in "a panoramic, case-specific

inquiry" that considers multiple factors, including "the

centrality of the tainted material," its "prejudicial impact," and

"the relative strengths of the parties' cases." Id. (quoting

instruction because that decision is 'within the ken of counsel and part of litigation strategy and judgment'").

- 22 - United States v. Sepúlveda, 15 F.3d 1161, 1182 (1st Cir. 1993)).

We conclude that the government has made the necessary showing.

As the government points out, the testimony by Mercado

that is at issue formed only one part of Mercado's testimony, and

that testimony was itself only part of the government's case.

Specifically, in testifying, Mercado did more than address his

understanding of the meaning of words that appeared in the

transcripts of his conversations with Carrasco. He also testified,

without objection from Carrasco, about the yearslong corrupt

relationship between the two of them, with specific reference to

the bribes and contracts charged in the indictment.

The evidence also included the many checks that Mercado

paid to Carrasco and Mercado's testimony about those checks.

Mercado testified in that respect that he made payments to Carrasco

for "[a]ccess" and "protection" due to his belief that Carrasco

had "[t]otal access" and "[t]otal influence" over the mayors in

the three municipalities at issue and that Mercado understood by

making those payments that Carrasco would ensure that Mercado

received municipal contracts.

Finally, as the government notes, the transcripts of the

recorded conversations were themselves in evidence. And the

transcripts on their face are plainly incriminating even setting

aside Mercado's testimony about the meaning of what was said in

them. For example, the transcript of one of the recorded

- 23 - conversations shows that Mercado mentioned explicitly to Carrasco

that investigators would be asking Mercado questions regarding

whether Mercado received "kickbacks" for "contracts" and that

Mercado could not "lie" about it. That transcript also shows that

Mercado then stated repeatedly, speaking only to Carrasco, that he

did not "have a way to justify that money" and that "out of the

checks we had, there were many . . . very close to . . . your

clients' contracts without any justification." Soon after,

according to the transcript, Carrasco stated: "If you at least get

me the information on the date and amount I could find out what

sort of things happened during, during those dates, because we may

have some sort of explanation. It's the only thing . . . if not

. . . we're screwed." (Emphasis added).

The government argues based on this evidence that the

recorded conversations themselves, in combination with the other

evidence, are enough to establish Carrasco's guilt even without

Mercado's commentary interpreting them. Yet Carrasco offers no

explanation for why the plain meaning of these comments does not

reflect a corrupt relationship between Mercado and Carrasco. He

thus offers no explanation for why the admission of Mercado's

interpretations of those conversations would not have been

harmless. And without any such explanation from Carrasco, we must

conclude that the record in this case "offers every assurance that

- 24 - the [challenged testimony] did not affect the trial's outcome" and

so was "harmless." Sepúlveda, 15 F.3d at 1182.

IV.

Carrasco separately challenges his 120-month prison

sentence as procedurally and substantively unreasonable. He does

so by advancing three preserved challenges to the District Court's

application of the Guidelines, as well as claims regarding the

disparity between his sentence and both the sentences imposed for

similar offenses nationwide and the sentence received by Mercado.

We begin with Carrasco's claims that his sentence is

procedurally unreasonable. We review the District Court's factual

determinations for clear error, its legal interpretation and

application of the sentencing guidelines de novo, and its judgement

calls for abuse of discretion. United States v. Ouellette, 985

F.3d 107, 110 (1st Cir. 2021).

1.

Carrasco first challenges the District Court's

application of the two-level enhancement that U.S.S.G. § 3C1.1

sets forth if:

the defendant willfully obstructed or impeded, or attempted to obstruct or impede, the administration of justice with respect to the investigation, prosecution, or sentencing of the instant offense of conviction, and [if] the obstructive conduct related to . . . the defendant's offense of conviction and any

- 25 - relevant conduct; or . . . a closely related offense.

The District Court determined that the enhancement applied to

Carrasco because Carrasco "attempt[ed] to convince . . . Mercado

. . . that the best strategy to face their problem was for them to

keep silent and not tell anything to anyone, to invoke the

attorney-client privilege to cover their scheme, or to lie to the

Federal Bureau of Investigation." The District Court based the

predicate determination on, among other things, a conversation

that Mercado recorded between himself and Carrasco at the behest

of law enforcement.10

To the extent that Carrasco contends that the District

Court clearly erred in determining that Carrasco had attempted to

10 That conversation went as follows: Mercado: And what about when they ask you, why was he your client? Carrasco: I cannot give out any details. Mercado: You know, they are going to ask that to me. And I am going to tell them, "Yes, he was my attorney." "What for?" Carrasco: For everything. Mercado: For this. . . Well, that would be lying to them. Carrasco: For everything, you understand. Mercado: You would say for everything? Carrasco: Yes, for everything.

- 26 - convince Mercado that Mercado should invoke attorney-client

privilege, we cannot agree. The District Court's reading of the

transcript is certainly a plausible one. See United States v.

Rivera, 51 F.4th 47, 53 (1st Cir. 2022) ("[W]here there is more

than one plausible view of the circumstances, the sentencing

court's choice among supportable alternatives cannot be clearly

erroneous." (quoting United States v. Ilarraza, 963 F.3d 1, 14

(1st Cir. 2020))).

Carrasco separately contends that, even if he engaged in

the conduct described above, the District Court erred by applying

the enhancement to him. He notes that Application Note 5 to

§ 3C1.1 lays out "a non-exhaustive list" of certain conduct which

"ordinarily do[es] not warrant application" of the enhancement.

He goes on to point out that Section B of that Note explains that

one type of conduct which "ordinarily" is insufficient to trigger

the enhancement is "making false statements, not under oath, to

Mercado: But, but I will earn myself eight years. Carrasco: No, no, wait a minute, I am not telling you to— Mercado: [Crosstalk] I mean, I don’t have . . . What evidence do I have? Carrasco: Listen to me. I am telling you about me, what I would say, "For everything."

- 27 - law enforcement officers, unless Application Note 4(G) above

applies." And, finally, he emphasizes that Application Note 4

lays out "a non-exhaustive list of examples of the types of

conduct" that justifies application of the enhancement, including

Section G, which provides that the enhancement applies if the

defendant "provid[ed] a materially false statement to a law

enforcement officer that significantly obstructed or impeded the

official investigation or prosecution of the instant offense."

See U.S.S.G. § 3C1.1 n.4 & n.5. Carrasco then pulls the argument

together by contending that his conduct is properly categorized as

an unsworn false statement to law enforcement under Application

Note 5(B) rather than as a "materially false statement to a law

enforcement officer that significantly obstructed or impeded the

official investigation or prosecution" under Application Note

4(G).11

In support of this contention, Carrasco argues that his

suggestion that Mercado lie to law enforcement could not have

To the extent Carrasco argues that the enhancement does not 11

apply to him at all because he made the statements in question to Mercado and Mercado was not a member of law enforcement, Carrasco misapprehends the reach of the enhancement. Under Application Note 9, Carrasco would be accountable both for his "own conduct and for conduct that [he] aided or abetted, counseled, commanded, induced, procured, or willfully caused." U.S.S.G. § 3C1.1 n.9. Because Carrasco advised Mercado to make a false claim of attorney-client privilege to law enforcement, the fact that Mercado rather than Carrasco would have actually lied to law enforcement would be no defense to the application of the enhancement to Carrasco.

- 28 - created the necessary significant obstruction or impediment under

Note 4(G), given that Mercado was already cooperating with law

enforcement. He further notes that, even if Mercado had not been

cooperating with law enforcement at the time, Application Note

4(G) applies only if the obstructive conduct "significantly

obstructed or impeded" an investigation or prosecution. For that

reason, Carrasco contends that the enhancement could not apply to

him because the District Court made no finding that his suggestion

to Mercado would have had such an impact if Mercado had not already

been cooperating with law enforcement and had instead, at

Carrasco's suggestion, claimed a nonexistent lawyer-client

confidentiality.

Carrasco ignores, however, the import of Application

Note 4(A), which makes the enhancement applicable when a defendant

"threaten[s], intimidat[es], or otherwise unlawfully influenc[es]

a . . . witness . . . directly or indirectly, or attempt[s] to do

so." U.S.S.G. § 3C1.1 n.4(A) (emphasis added). While Carrasco

contends that he did not attempt to "threaten[]" or "intimidat[e]"

Mercado, we have previously explained that simply asking a

potential witness to lie to law enforcement "plainly constitutes

an attempt to 'unlawfully influenc[e] a . . . witness.'" United

States v. Coffin, 946 F.3d 1, 8 (1st Cir. 2019); see also United

States v. Batchu, 724 F.3d 1, 12 (1st Cir. 2013); cf. United States

v. O'Brien, 870 F.3d 11, 18 (1st Cir. 2017). Because Carrasco

- 29 - does not explain why our reasoning in such cases is not applicable

here, we reject his challenge to the application of the obstruction

of justice enhancement to him.

2.

Carrasco next contends that the District Court erred in

applying a two-level enhancement based on § 2C1.1(a)(1) of the

Guidelines. He does so on the ground that the District Court was

wrong to treat him as a "public official" within the meaning of

that Guideline.

In applying the enhancement, the District Court relied

on the first Application Note to § 2C1.1. The District Court noted

that the Application Note provides that the term "'public official'

shall be construed broadly." U.S.S.G. § 2C1.1 n.1. It also noted

that Section C of that Application Note provides that the term

"public official" includes:

[a]n officer or employee or person acting for or on behalf of a state or local government, or any department, agency, or branch of government thereof, in any official function, under or by authority of such department,

- 30 - agency, or branch of government, or a juror in a state or local trial.

Id. § 2C1.1 n.1(C).

The District Court also noted that Section E of that

Application Note provides in relevant part that a "public official"

includes:

[a]n individual who . . . (i) is in a position of public trust with official responsibility for carrying out a government program or policy; (ii) acts under color of law or official right; or (iii) participates so substantially in government operations as to possess de facto authority to make governmental decisions (e.g., which may include a leader of a state or local political party who acts in the manner described in this subdivision).

Id. § 2C1.1 n.1(E).

In contending that the District Court was wrong to apply

the enhancement, Carrasco argues that the record indisputably

shows that he was never appointed or elected to any office, that

he was not employed by the municipalities for whom he performed

contract services, and that "his contractual relationship was not

shown to afford him decision-making authority or any other indicia

of public trust." He thus contends that there was no basis for

applying the enhancement set forth in the Guideline to him.

But the District Court explained that its determination

that Carrasco was a "public official" was based on "the duties

that [he] assumed and performed under his contracts with the

- 31 - [m]unicipalities of Barceloneta, Rio Grande, and Juncos" and that,

in the District Court's view, Carrasco "was in a position of public

trust that infused him with enough de facto authority to act for

or on behalf of those municipalities and influence the

decision-making process, particularly as it relate[d] to ensuring

that the municipalities awarded contracts to . . . Mercado."

Moreover, shortly before denying Carrasco's objection to the

application of the sentence enhancement to him, the District Court

had denied Carrasco's objection to the presentence report's

description of Carrasco as "the main advisor/attorney for the

mayors of Barceloneta, Rio Grande, and Juncos" and, in doing so,

had pointed to Mercado's testimony that Carrasco had close

relationships with all three mayors and had "total influence" over

each of them.

We thus conclude that the District Court determined,

albeit implicitly, that Mercado's testimony detailing Carrasco's

relationships with the mayors supported a finding that, by a

preponderance of the evidence, Carrasco "participate[d] so

substantially in government operations as to possess de facto

authority to make governmental decisions." U.S.S.G. § 2C1.1

n.1(E)(iii). Carrasco's only argument for why the District Court

would have been wrong to so conclude, however, is that Carrasco

was, at most, only an "advisor" to the mayors. Yet this argument

fails to grapple with Mercado's testimony that Carrasco had "total

- 32 - influence" over the mayors, as it is difficult to see how Carrasco

could be understood to have "total influence" over the mayors if

he did not have "de facto authority to make . . . decisions"

regarding to whom the contracts would be awarded. We thus see no

error in the District Court's application of this enhancement to

Carrasco.

3.

Carrasco's final Guidelines-related contention is that

the District Court erred by applying a four-level enhancement to

him under § 2C1.1(b)(3). That guideline provides that the

enhancement applies when the "offense involved an elected public

official or any public official in a high-level decision-making or

sensitive position." Id. Carrasco argues that the guideline has

no application to him because he "was not convicted of bribing an

elected official or with joining with Mercado to do so."

Carrasco misapprehends the basis for the District

Court's application of the enhancement. The District Court did

not apply the enhancement because Carrasco was found to be part of

a scheme to pay the mayors in exchange for the award of contracts.

It did so because it determined that Carrasco "used his influence

over and his access to the mayors of the [m]unicipalities of

Barceloneta, Rio Grande, and Juncos, who are elected public

officials," to steer contracts to Mercado and because Carrasco

- 33 - himself was a "public official" in a "high level decision-making

or sensitive position."

Carrasco makes no argument that the District Court's

determination on either point was incorrect. And even if we were

to disregard the former determination, Carrasco makes no argument

that the latter determination -- that Carrasco himself was a

"public official in a high-level decision-making or sensitive

position" -- would not have alone been sufficient to justify the

application of the enhancement. See United States v. Hill, 645

F.3d 900, 908 (7th Cir. 2011) (affirming application of

§ 2C1.1(b)(3) enhancement to defendant based on finding that

defendant "held a sensitive position").

Nor can we see how the determination that Carrasco was

a "public official in a high-level decision-making or sensitive

position" was incorrect. We explained above that the District

Court was not wrong to find that Carrasco had "de facto authority

to make governmental decisions" when applying an enhancement to

him for being a "public official." We also conclude that the

District Court was not wrong to determine on this same basis that

Carrasco occupied a "high-level decision-making position," given

that such a position is "characterized by a direct authority to

make decisions" for the municipalities. We thus see no mistake in

the District Court's application of this enhancement to Carrasco.

- 34 - B.

Finally, we address Carrasco's challenges to the

substantive reasonableness of his sentence. Our review is for

abuse of discretion, United States v. Reyes-Torres, 979 F.3d 1, 9

(1st Cir. 2020), and we uphold a sentence against such a challenge

so long as the district court provided "a plausible sentencing

rationale" in support of "a defensible result," United States v.

Contreras-Delgado, 913 F.3d 232, 243 (1st Cir. 2019) (quoting

United States v. Zapata-Vázquez, 778 F.3d 21, 24 (1st Cir. 2015)).

Carrasco's first substantive-reasonableness-based

challenge is that the District Court created an unjustified

disparity between his sentence and the sentences imposed on

similarly situated defendants nationally. This disparity argument

rests on the contention that the District Court erred in declining

to credit statistics showing that the average sentence in the

United States for a bribery-related offense was twenty-five months

in 2019. Carrasco, relying on these statistics, contends that the

District Court should have sentenced him to a comparable period of

incarceration.

But a claim of national disparity relies on "apples . . .

being compared to apples," United States v. Joubert, 778 F.3d 247,

256 (1st Cir 2015). And, as the District Court correctly noted,

various statistical measures of the average sentences imposed upon

- 35 - defendants convicted of bribery offenses include sentences imposed

upon defendants convicted under a number of federal statutes, not

just defendants who, like Carrasco, were convicted for violating

18 U.S.C. § 666. Thus, the District Court committed no error in

finding that Carrasco's statistics were over-inclusive and thus

provided no basis for a claim of national disparity.12

Carrasco's second challenge to the substantive

reasonableness of his sentence is another disparity-based

challenge. Here, he contends that the District Court erred in

sentencing him to 120 months of imprisonment when Mercado was

sentenced only to a pretrial diversion program. But, as with his

claim of national disparity, Carrasco must convince us that he and

Mercado were similarly situated. United States v. Gonzalez, 981

F.3d 11, 23 (1st Cir. 2020). Yet Carrasco cannot do so given the

substantial differences between Mercado and Carrasco, which

12 Carrasco also challenges the procedural reasonableness of his sentence based on what he contends was an inappropriate reference by the District Court to other sentences handed down for violations of § 666 in the District of Puerto Rico. But, the District Court made clear that it was not "purport[ing] to hold [Carrasco] responsible for all of the wrongs caused by corruption in Puerto Rico" and that the District Court was "required to impose a sentence that is commensurate" to his "offenses" and "personal characteristics" as well as the sentence's deterrent effect. Carrasco does not explain why, despite these statements by the District Court, we must understand the District Court to have impermissibly relied on community characteristics in determining his sentence.

- 36 - include the fact that Mercado cooperated with law enforcement and

Carrasco did not. Cf. United States v. Mateo-Espejo, 426 F.3d

508, 514 (1st Cir. 2005) (rejecting sentencing disparity claim in

light of "appellant's belated and grudging cooperation" compared

to codefendant's "prompt and full cooperation").13

Carrasco's final substantive-reasonableness challenge

to his sentence is that the District Court erred in sentencing him

to the statutory maximum. As Carrasco himself acknowledges, the

statutory maximum for the offenses of which he was convicted is

one month below the lower end of the calculated Guidelines range.

Nonetheless, Carrasco objects to the District Court's refusal to

vary even further downward in light of what he characterizes as

"the overwhelmingly mitigating personal considerations" present in

his case.

But the District Court at the sentencing hearing

explicitly considered the mitigating circumstances to which

Carrasco directs our attention. Indeed, after taking note of

13 To the extent Carrasco claims that the District Court imposed a penalty upon him for not pleading guilty, the claim fails for similar reasons: Carrasco cannot show that any similarly situated codefendant received a lesser sentence simply because he went to trial rather than pleading guilty, particularly given that, in handing down Carrasco's sentence, the District Court noted that the mayor of Barceloneta received the same sentence "even though he pled guilty and less money was involved" in the crimes to which to mayor pled guilty than the crimes of which Carrasco was found guilty.

- 37 - Carrasco's age, family, and multiple medical conditions, the

District Court also noted that Carrasco had worked as an attorney

"for more than 30 years" and that Carrasco had submitted "many

letters of recommendation" that spoke to his "good moral character

and values" and that "describe[d] him as an exemplary son, father,

and friend, and as an honorable citizen and consummate professional

. . . who still has much to offer." The District Court then noted,

however, that none of those letters mentioned Carrasco's

corruption convictions and that "it would not be honest or show

integrity" for an attorney to "do what [Carrasco] was convicted of

doing in this case over five years," such as "accept[ing] bribes,

cover[ing] up a scheme involving paying bribes, or telling someone

to lie concerning the bribe scheme." The District Court therefore

concluded that the 120-month guideline sentence was "the

appropriate punishment pursuant to the facts of this case and in

accordance with the [§] 3553(a) factors." We cannot conclude that

the District Court's conclusion on this score was predicated on

implausible reasoning or yielded an indefensible result. We thus

reject Carrasco's challenge.

For the above reasons, we affirm Carrasco's convictions

and his sentence.

- 38 -