Court Opinion

ID: 9573895
Source: CourtListenerOpinion
Date Created: 2023-08-21 21:00:17.656582+00
Date Added: 2024-06-11T13:22:18.423563
License: Public Domain

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 21

U.S.C. § 846 and (2) conspiracy to import a controlled substance

into the United States in violation of 21 U.S.C. § 963.                 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, 776 F.3d 45, 47 (1st Cir. 2015); United States v. Dávila-

González, 595 F.3d 42, 45 (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

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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

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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

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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 18 U.S.C.

§ 3553 regarding his cooperation with the government; and (3) that

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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, 5 F.4th 104, 107 (1st Cir. 2021) (quoting United States

v. Ilarraza, 963 F.3d 1, 7 (1st Cir. 2020)).          The first two

arguments Coplin advances are claims of procedural error, see

United States v. Laureano-Pérez, 797 F.3d 45, 80 (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, 939 F.3d 310, 319 (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.

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           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, 51 F.4th 12,

28 (1st Cir. 2022) (quoting United States v. Appolon, 695 F.3d 44,

70 (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, 5 F.4th at 107

(quoting United States v. McCormick, 773 F.3d 357, 359 (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,

782 F.3d 26, 29 (1st Cir. 2015) (quoting United States v. Graciani,

61 F.3d 70, 75 (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

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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, 51 F.4th at 28 (alterations in original)

(quoting United States v. Hernández, 964 F.3d 95, 101 (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, 895
F.2d 1, 17 (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." Id.

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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, 51 F.4th 47, 52 (1st Cir.

2022) (quoting United States v. Tejada-Beltran, 50 F.3d 105, 111

(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, 51 F.4th at 28 (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

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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, 964 F.3d at 102-05 (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, 695 F.3d at 70; United States v. Casas, 356 F.3d 104, 129

(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

18 U.S.C. § 3553.

            Preserved claims of procedural sentencing error are

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

Viloria-Sepulveda, 921 F.3d 5, 8 (1st Cir. 2019) (citing Gall v.

United   States,   552   U.S.   38,    55    (2007)).     Coplin     raised   the

governmental cooperation argument before the district court, so it

is preserved.

            Under 18 U.S.C. § 3553, 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.    18 U.S.C. § 3553(a)(1).         This broad provision includes

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

United States v. Landrón-Class, 696 F.3d 62, 77 (1st Cir. 2012).

We have thus held that a sentencing court has discretion under

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

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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 18 U.S.C. § 3553."          Landrón-Class, 696 F.3d at 78

(quoting United States v. Turbides–Leonardo, 468 F.3d 34, 40–41

(1st Cir.2006)); see also United States v. Dixon, 449 F.3d 194,

205 (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

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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, 963 F.3d

145, 152 (1st Cir. 2020) (quoting United States v. Lozada-Aponte,

689 F.3d 791, 793 (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     18,       United    States    Code,     Section

3553(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, 921 F.3d at 8 (citing Gall, 552 U.S. at 55).                             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." 18 U.S.C. § 3553(a)(6); see also United States v. Reyes-

Santiago, 804 F.3d 453, 467 (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, 804 F.3d at 467

(first quoting United States v. Rivera-Gonzalez, 626 F.3d 639, 648

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

778 F.3d 363, 366 (1st Cir. 2015)).

            To   establish   a   well-founded         claim    of    sentencing

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

467.   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, 842 F.3d 8, 15 (1st Cir. 2016); see also Reyes-Santiago,

804 F.3d at 467 ("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

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

Martínez and Andino.      Cf. Reverol-Rivera, 778 F.3d at 366 (noting

"differences in culpability can justify disparate sentences among

co-defendants"); United States v. Rivera–Maldonado, 194 F.3d 224,

236 (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, 842 F.3d at

15.

           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.

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