United States Court of Appeals For the First Circuit

No. 21-1737

UNITED STATES OF AMERICA,

Appellee,

v.

BERNARDO COPLIN-BENJAMIN,

Defendant, Appellant.

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

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

Before

Kayatta, Howard, and Thompson, Circuit Judges.

Luis Rafael Rivera for appellant. Maarja T. Luhtaru, Assistant United States Attorney, with whom W. Stephen Muldrow, United States Attorney, Mariana E. Bauzá– Almonte, Assistant United States Attorney, and Julia M. Meconiates, Assistant United States Attorney, were on brief, for appellee.

August 21, 2023 HOWARD, Circuit Judge. On August 8, 2019, Bernardo

Coplin-Benjamin pleaded guilty to (1) conspiracy to possess with

the intent to distribute a controlled substance in violation of

and (2) conspiracy to import a controlled substance

into the United States in violation of

. The

district court sentenced him to 262 months' imprisonment. On

appeal, Coplin challenges both the procedural and substantive

reasonableness of his sentence. For the following reasons, we

affirm.

I.

Because this appeal follows a straight guilty plea

without a plea agreement, we glean the relevant facts from the

unchallenged portions of the presentence investigation report

(PSR) and the sentencing hearing. See United States v. Rivera–

González,

(1st Cir. 2015); United States v. Dávila-

González,

(1st Cir. 2010).

On January 27, 2018, federal agents intercepted a vessel

named the "Black Wolfpack" that was suspected of transporting drugs

from St. Thomas, United States Virgin Islands, to Fajardo, Puerto

Rico. The individuals on the vessel at the time were identified

as Maximiliano Figaro-Benjamín, Emiliano Figaro-Benjamín, Katerín

Martínez-Alberto, and Alexandria Andino-Rodríguez.

During multiple searches of the Black Wolfpack, agents

found approximately 132 kilograms of cocaine (worth about three

- 2 - million dollars) hidden in bundles in multiple locations on the

vessel. Agents also found a WhatsApp chat on Maximiliano Figaro-

Benjamín's phone between him and Coplin discussing the drug

trafficking venture. The messages showed them discussing the

distribution of 130 kilograms of cocaine as well as details like

the number of packages, cost per package, estimated departure date,

and a meeting in St. Thomas. The messages showed that Coplin had

spoken directly to the narcotics supplier in St. Thomas to discuss

the price per kilogram of cocaine transported. Additional

discovery showed that Coplin was in regular communication with the

key individuals from the January 27, 2018, seizure throughout the

duration of the vessel's trip and thereafter.

Coplin was arrested on February 22, 2019. On August 8,

2019, he entered a straight guilty plea for conspiracy to possess

with the intent to distribute a controlled substance and conspiracy

to import a controlled substance.

Several of Coplin's co-defendants opted to proceed to

trial. The testimony at trial revealed details about the drug

trafficking conspiracy and the acts preceding the St. Thomas-

Puerto Rico trip in which the Black Wolfpack was seized. A co-

defendant named Javier Resto-Miranda testified that he would buy

drugs from Coplin to sell in Alaska and that, during the course of

these dealings, "the idea came up of purchasing a vessel to buy

drugs in St. Thomas and bring them to Puerto Rico." Resto

- 3 - indicated that Coplin had had the idea and asked to put the vessel

in Resto's name. The vessel was purchased but ultimately seized.

However, Coplin had another vessel, named Wasikoki. Coplin again

talked about the possibility of trafficking drugs from St. Thomas

to Puerto Rico, this time with the Wasikoki. Resto testified that

Coplin "asked [him] to get somebody who could take [them] to St.

Thomas so [they] could learn about the route, how much gas would

be needed, how much fuel, how much time." He said they arrived in

St. Thomas and Coplin asked Resto to propose to the captain doing

a test run with two kilograms of cocaine. On one trip, Resto

called Coplin for guidance on how to proceed when a boat didn't

work properly, and Coplin advised him to wait and check later.

Coplin later gave Resto $30,000 to purchase the Black

Wolfpack vessel. Resto testified that before every trip, Coplin

would plan, would meet with the members of the conspiracy, and

would tell Resto "what had to be done." He testified that Coplin

was the one to pay the other co-defendants and that he gave them

money for gas, food, and supplies for the trip. Resto also

testified that Coplin and his business partner would count the

money at Coplin's home.

Based on this testimony and the other facts outlined in

the PSR, the probation officer classified Coplin as a leader of a

criminal activity involving five or more participants and

therefore added a four-level enhancement. Coupled with a base

- 4 - level offense of 36 and multiple other calculations not relevant

on appeal, the total offense level was 39. The recommended

guideline range was 262 to 327 months' imprisonment.

Coplin filed a written objection to the PSR, arguing

"that he does not deserve to be labeled as a leader in this case

as he was not in charge of the overall operation and was not

putting his own money to develop . . . the drug venture." He did

not challenge the underlying factual allegations and testimony.

He also argued at his sentencing hearing that he should receive a

downward adjustment for cooperating with the government and that

the government's proposed sentence for Coplin was disproportionate

to those of coconspirators, among other arguments not relevant on

appeal. The district court denied Coplin's objections, found that

he was a leader and not a supervisor, and did not give him credit

for cooperation with the government. The court sentenced Coplin

to 262 months' imprisonment.

II.

The key arguments Coplin advances on appeal are (1) that

he was a "supervisor" and not a "leader," so the district court

should not have applied the four-level leadership enhancement; (2)

that the court failed to consider factors set out in

regarding his cooperation with the government; and (3) that

- 5 - his sentence was substantively unreasonable given that he received

a much longer sentence than several co-defendants.1

We review claims of sentencing errors in two steps: "We

first examine any claims of procedural error. If the sentence

clears these procedural hurdles, we then consider any claim that

questions its substantive reasonableness." United States v.

McKinney,

(1st Cir. 2021) (quoting United States

v. Ilarraza,

(1st Cir. 2020)). The first two

arguments Coplin advances are claims of procedural error, see

United States v. Laureano-Pérez,

(1st Cir. 2015),

so we begin there, taking each in turn.

A.

1 During oral argument, Coplin's counsel also advanced an argument (not included in his briefing on appeal) that the base offense level of 36 was incorrect because it was based on the offense involving at least 150 but less than 450 kilograms of cocaine, whereas agents only seized 132 kilograms on the Black Wolfpack. Counsel suggested that this discrepancy was "overlooked" by everyone and asked for review for clear error based on a miscarriage of justice even though arguments raised for the first time at oral argument are considered waived. See, e.g., United States v. Leoner-Aguirre,

(1st Cir. 2019). However, the circumstances here contradict counsel's argument. The district court transcript makes clear that defense counsel, the prosecutor, and the district judge all discussed this issue at the sentencing hearing. The government's position at sentencing was that there was evidence of other trips in the drug trafficking conspiracy involving additional kilograms of cocaine beyond the 132 seized on the Black Wolfpack. The district judge agreed with this offense level calculation and denied defense counsel's objection to it. It is therefore clear that this issue was not merely "overlooked," and Coplin's counsel on appeal has not advanced any other argument that the calculation was incorrect.

- 6 - Coplin first challenges the district court's imposition

of a four-level enhancement based on Coplin's role as a leader of

the criminal activity. "We review the imposition of this

particular sentencing enhancement, and any predicate factual

findings, for clear error." United States v. Ahmed,

(1st Cir. 2022) (quoting United States v. Appolon,

(1st Cir. 2012)). "Where the raw facts are susceptible to

competing inferences, the sentencing court's choice between those

inferences cannot be clearly erroneous." McKinney,

(quoting United States v. McCormick,

(1st Cir.

2014)). "Given this deferential standard of review, battles over

a defendant's role in the offense 'will almost always be won or

lost in the district court.'" United States v. Meléndez-Rivera,

(1st Cir. 2015) (quoting United States v. Graciani,

(1st Cir. 1995)).

The federal Sentencing Guidelines provide for a four-

level enhancement "[i]f the defendant was an organizer or leader

of a criminal activity that involved five or more participants or

was otherwise extensive." U.S.S.G. § 3B1.1(a). By contrast, the

guidelines provide for only a three-level enhancement "[i]f the

defendant was a manager or supervisor (but not an organizer or

leader) and the criminal activity involved five or more

participants or was otherwise extensive." Id. at § 3B1.1(b).

These enhancements require both a status determination of whether

- 7 - the defendant acted as an "organizer or leader" or "manager or

supervisor," as well as a determination of the scope of the

criminal activity -- i.e., "that the criminal activity met either

the numerosity or the extensiveness benchmarks established by the

[G]uideline[s]." Ahmed,

(alterations in original)

(quoting United States v. Hernández,

(1st Cir.

2020)). On appeal, Coplin focuses solely on the status

determination rather than the scope of criminal activity. He

argues that he was merely a supervisor and not a leader, therefore

warranting a three-level increase instead of four.2

In making the determination of whether someone is an

"organizer or leader" or merely a "manager or supervisor," courts

should consider "the exercise of decision making authority, the

nature of participation in the commission of the offense, the

recruitment of accomplices, the claimed right to a larger share of

the fruits of the crime, the degree of participation in planning

or organizing the offense, the nature and scope of the illegal

2 The government argues that Coplin has waived this argument on appeal given that Coplin's discussion of this issue is just over a page and contains no standard of review or citations to case law. We have repeatedly held that "issues adverted to in a perfunctory manner, unaccompanied by some effort at developed argumentation, are deemed waived." United States v. Zannino,

(1st Cir. 1990). We need not here determine whether the brevity of Coplin's argument constituted waiver, given that it fails on the merits. However, we reiterate that "[i]t is not enough merely to mention a possible argument in the most skeletal way, leaving the court to do counsel's work, create the ossature for the argument, and put flesh on its bones."

- 8 - activity, and the degree of control and authority exercised over

others." U.S.S.G. § 3B1.1 cmt. n.4. "This list is 'representative

rather than exhaustive,' and 'proof of each and every factor' is

not necessary to establish that a defendant acted as an organizer

or leader." United States v. Rivera,

(1st Cir.

2022) (quoting United States v. Tejada-Beltran,

(1st Cir. 1995)). For the enhancement to apply, the defendant

"must have led or organized at least one other criminal actor --

and not just a criminal activity -- on at least one occasion."

Ahmed,

(emphases in original).

In conducting this assessment, the district court

recited many of the undisputed facts from the PSR regarding co-

defendant Resto's testimony. The court noted that Resto testified

that Coplin initiated the conspiracy with the idea of purchasing

a vessel to buy drugs in St. Thomas and bring them to Puerto Rico.

Resto testified that Coplin twice directed him to buy vessels and

gave him $30,000 to buy the second vessel, which was the Black

Wolfpack. He further testified that Coplin initiated and directed

several trips, including asking Resto to go St. Thomas to learn

more details about the route and asking him to propose running a

test trip with two kilograms of cocaine. Resto indicated that,

before every trip, Coplin would plan, meet with the coconspirators,

tell them what they needed to do, and give them petty cash for

food, gas, and supplies. Coplin and his business partner counted

- 9 - the money in Coplin's home, and Coplin was the one to pay co-

defendants.

On appeal, Coplin does not advance any argument that

these findings are inaccurate or that they fail to show that he

led or organized at least one coconspirator on at least one

occasion. Cf. Hernández,

(concluding organizer

enhancement was warranted where defendant instructed coconspirator

on one occasion). Rather, Coplin points to the existence of

another "leader that was paying for everything and that was

providing the strategic overview of the operation" as the sole

basis for finding that Coplin "had a smaller part and played a

role akin to a manager." But the Sentencing Guidelines and our

case law make clear that the existence of another leader -- even

one superior to Coplin in the scheme's hierarchy -- does not

foreclose the possibility of Coplin also acting as a leader. See

Appolon,

; United States v. Casas,

(1st Cir. 2004) ("The mere fact that [the defendant] was

subordinate to [a coconspirator] does not establish, without more,

that [he] was not an organizer or leader of the conspiracy.");

U.S.S.G. § 3B1.1 cmt. n.4 ("There can, of course, be more than one

person who qualifies as a leader or organizer of a criminal

association or conspiracy."). Standing alone, this argument

therefore cannot invalidate the district court's finding that

Coplin was a leader himself. Coplin advances no other arguments

- 10 - in support of his contention, and the district court's factual

findings regarding Coplin's role in the conspiracy certainly

support the inference that Coplin was indeed a leader. The

district court therefore did not clearly err in applying the four-

level enhancement.

B.

Coplin's second procedural argument is that the district

court failed to consider his cooperation with the government under

.

Preserved claims of procedural sentencing error are

reviewed under an abuse of discretion standard. United States v.

Viloria-Sepulveda,

(1st Cir. 2019) (citing Gall v.

United States,

(2007)). Coplin raised the

governmental cooperation argument before the district court, so it

is preserved.

Under

, a sentencing court must consider

"the nature and circumstances of the offense and the history and

characteristics of the defendant" in determining the appropriate

sentence.

(a)(1). This broad provision includes

as a factor "the defendant's cooperation with the government."

United States v. Landrón-Class,

(1st Cir. 2012).

We have thus held that a sentencing court has discretion under

§ 3553 to consider a defendant's cooperation with the government

- 11 - even if the government has not made a U.S.S.G. § 5K1.1 motion for

a downward departure in sentencing. Id.

Here, however, there is no indication that the district

court failed to consider the defendant's cooperation with the

government. During the sentencing hearing, defense counsel raised

the issue of cooperation at the outset, and the government attorney

responded in depth. The government's position, reiterated on

appeal before this court, was that although the defendant had met

with the government on three different occasions, he had not

substantially assisted the government and had not identified any

coconspirators by name until the third interview. After hearing

these arguments, among others, the district court did not apply

any downward adjustments for cooperation with the government.

It is true that the district court did not explicitly

mention Coplin's cooperation in discussing the imposed sentence.

But "a sentencing court is not required to address frontally every

argument advanced by the parties, nor need it dissect every factor

made relevant by

." Landrón-Class,

(quoting United States v. Turbides–Leonardo,

, 40–41

(1st Cir. 2006)); see also United States v. Dixon,

(1st Cir. 2006) (a sentencing court "is not required to address

[the § 3553(a)] factors, one by one, in some sort of rote

incantation"). "When a defendant has identified potentially

mitigating sentencing factors and those factors are thoroughly

- 12 - debated at sentencing, the fact that the court 'did not explicitly

mention them during the sentencing hearing suggests they were

unconvincing, not ignored.'" United States v. Díaz-Lugo,

(1st Cir. 2020) (quoting United States v. Lozada-Aponte,

(1st Cir. 2012)). Here, the district court heard

arguments by both parties on the issue of governmental cooperation

and explicitly noted that it had "considered the . . . sentencing

factors set forth in Title

(a)." We therefore find Coplin's argument that the court

failed to consider this factor unavailing.

C.

We next turn to Coplin's claim that his sentence was

substantively unreasonable due to the disparity between his

sentence and those of two co-defendants.

We review preserved challenges to the substantive

reasonableness of a sentence for abuse of discretion. See Viloria-

Sepulveda,

(citing Gall,

). Coplin

raised this argument before the district court, so it is preserved.

Under § 3553(a)(6), courts are directed to consider "the

need to avoid unwarranted sentence disparities among defendants

with similar records who have been found guilty of similar

conduct."

(a)(6); see also United States v. Reyes-

Santiago,

(1st Cir. 2015). This provision is

"primarily aimed at national disparities, rather than those

- 13 - between co-defendants," but a sentence may nevertheless be

"substantively unreasonable because of the disparity with the

sentence given to a codefendant." Reyes-Santiago,

(first quoting United States v. Rivera-Gonzalez,

(1st Cir. 2010); and then quoting United States v. Reverol-Rivera,

(1st Cir. 2015)).

To establish a well-founded claim of sentencing

disparity, a defendant must "compare apples to apples."

. Where "material differences between the defendant and the

proposed comparator suffice to explain the divergence," a

sentencing disparity claim is unlikely to prevail. United States

v. Demers,

(1st Cir. 2016); see also Reyes-Santiago,

("We have routinely rejected disparity claims . . .

because complaining defendants typically fail to acknowledge

material differences between their own circumstances and those of

their more leniently punished confederates.").

Here, Coplin compares his sentence of 262 months to the

60-month sentence and 120-month sentence of coconspirators Katerín

Martínez-Alberto and Alexandria Andino-Rodríguez, respectively.

Coplin notes that both the coconspirators proceeded to trial

whereas he pleaded guilty and calls it "foul play" that his

sentence then exceeded theirs by more than a decade. But Coplin

fails to address key ways in which he is not similarly situated to

these co-defendants. Chiefly, as the district court found, Coplin

- 14 - was a leader of the conspiracy and not a mere participant like

Martínez and Andino. Cf. Reverol-Rivera,

(noting

"differences in culpability can justify disparate sentences among

co-defendants"); United States v. Rivera–Maldonado,

(1st Cir. 1999) (finding a leader and subordinates were not

similarly situated). These co-defendants therefore are not fair

comparators, and we cannot find an unwarranted sentencing

disparity here.

Furthermore, the court sentenced Coplin on the lowest

end of the guideline range, which, as we have explained above, was

properly calculated. "A challenge to the substantive

reasonableness of a sentence is particularly unpromising when the

sentence imposed comes within the confines of a properly calculated

[guideline sentencing range]," "particularly . . . where, as here,

the sentence is at the nadir of the range." Demers,

.

Based on the foregoing, we find that the district court

did not abuse its discretion in imposing a 262-month sentence.

III.

For the reasons above, the sentence is affirmed.

- 15 -