22-1804(L) United States v. Frias
United States Court of Appeals For the Second Circuit
August Term 2023
Argued: March 19, 2024 Decided: May 16, 2024
Nos. 22-1804(L), 22-3083(Con)
UNITED STATES OF AMERICA,
Appellee,
v.
ADRIAN ESTERAS, AKA CHILLY, SHANE WILLIAMS,
Defendants,
CARLOS ESTERAS, RAPHAEL FRIAS, AKA RALPH, AKA RAFAEL FRIAS,
Defendants-Appellants.
Appeal from the United States District Court for the Northern District of New York No. 21-cr-269, Glenn T. Suddaby, Judge.
Before: CARNEY, SULLIVAN, and LEE, Circuit Judges.
Carlos Esteras and Raphael Frias appeal their sentences after entering pleas of guilty to fentanyl trafficking charges. Each argues that the district court (Suddaby, J.) erred in calculating his respective Guidelines range. Specifically, Esteras contends that the district court erroneously calculated his base offense level by applying a two-level increase under U.S.S.G. § 2D1.1(b)(12) for “maintain[ing] a premises” for narcotics trafficking and declining to apply a two- level reduction under U.S.S.G. § 3B1.2(b) for being a “minor participant” in the trafficking scheme. He also argues that the district court wrongly applied a two- point increase to his criminal history score under U.S.S.G. § 4A1.1(d) after finding that he was on parole at the time of the offense. Frias likewise asserts that the district court erred in applying the two-level premises enhancement under section 2D1.1(b)(12); he also contends that the district court improperly applied a four- level increase under U.S.S.G. § 3B1.1(a) for being an “organizer or leader” of the scheme and failed to adequately consider his mitigating evidence in declining to vary downwards. We affirm each of the district court’s sentencing decisions except its application of the “organizer or leader” enhancement under section 3B1.1(a) to Frias. Accordingly, we AFFIRM Esteras’s sentence and VACATE and REMAND Frias’s sentence for further proceedings consistent with this opinion.
AFFIRMED IN PART, VACATED IN PART, AND REMANDED.
Cory Zennamo, Zennamo Litigation & Advocacy, PLLC, Ilion, NY, for Defendant- Appellant Carlos Esteras.
ELIZABETH FRANKLIN-BEST, Elizabeth Franklin- Best, P.C., Columbia, SC, for Defendant- Appellant Raphael Frias.
THOMAS R. SUTCLIFFE, Assistant United States Attorney, for Carla B. Freedman, United States Attorney for the Northern District of New York, Syracuse, NY, for Appellee.
2 RICHARD J. SULLIVAN, Circuit Judge:
Carlos Esteras and Raphael Frias appeal their sentences after entering pleas
of guilty to fentanyl trafficking charges. Each argues that the district court
(Suddaby, J.) erred in calculating his respective Guidelines range. Specifically,
Esteras contends that the district court erroneously calculated his base offense
level by applying a two-level increase under U.S.S.G. § 2D1.1(b)(12) for
“maintain[ing] a premises” for narcotics trafficking and declining to apply a two-
level reduction under U.S.S.G. § 3B1.2(b) for being a “minor participant” in the
trafficking scheme. He also argues that the district court wrongly applied a two-
point increase to his criminal history score under U.S.S.G. § 4A1.1(d) after finding
that he was on parole at the time of the offense. Frias likewise asserts that the
district court erred in applying the two-level premises enhancement under section
2D1.1(b)(12); he also contends that the district court improperly applied a four-
level increase under U.S.S.G. § 3B1.1(a) for being an “organizer or leader” of the
scheme and failed to adequately consider his mitigating evidence in declining to
vary downwards. We affirm each of the district court’s sentencing decisions
except its application of the “organizer or leader” enhancement under section
3 3B1.1(a) to Frias. Accordingly, we AFFIRM Esteras’s sentence and VACATE and
REMAND Frias’s sentence for further proceedings consistent with this opinion.
I. BACKGROUND
A. Investigation and Defendants’ Arrests
In late 2020, federal agents received information that Esteras and Frias
(together, “Defendants”) were selling fentanyl in the Syracuse area. Within a few
months, agents began conducting controlled buys from both Defendants, as well
as intercepting calls and texts on their phones. Investigators soon determined that
Defendants were collaborating with one another as part of a larger, dispersed
network of fentanyl distributors. Though Defendants obtained fentanyl from
separate suppliers and typically sold to different customers, they had an
agreement to supply each other’s customers if either was unavailable. Esteras
generally stored his fentanyl at his residence, while Frias stored his supply at the
apartment of his mother, who helped Frias sell that fentanyl to customers on
several documented occasions. Both Defendants also relied on other associates to
help distribute their fentanyl supplies, including codefendants Adrian Esteras and
Shane Williams (neither of whom is part of this appeal) and several other
4 subdistributors who bought fentanyl in bulk from Frias and resold it to other
customers.
Federal officers arrested Defendants in July 2021. When searching Esteras’s
residence, agents found 66.9 grams of fentanyl in bags, 166 glassine envelopes
containing a total of two grams of fentanyl, and two stamps used to mark
envelopes containing fentanyl. Esteras thereafter admitted that he had been
“obtaining between 30 and [40] bricks of fentanyl from his source of supply every
week for the past year.” Esteras Presentence Investigation Report (“PSR”) ¶ 28;
see also Esteras App’x at 53 n.1 (correcting a mistranscription in Esteras’s PSR that
incorrectly stated that he had obtained between “30 and 150” bricks per week).
Esteras ultimately admitted, as part of his plea, to distributing at least 124 grams
of fentanyl.
Agents likewise found thirteen grams of fentanyl in Frias’s mother’s
apartment, along with multiple bundles of glassine envelopes. As part of his plea,
Frias admitted that he distributed, or reasonably could have foreseen the
distribution of, at least 132 grams of fentanyl.
5 B. Esteras’s Sentencing
Esteras pleaded guilty to one count of conspiring to distribute and possess
with intent to distribute a controlled substance, in violation of 21 U.S.C.
§§ 841(a)(1) and 846, and one count of possession with intent to distribute a
controlled substance, in violation of 21 U.S.C. § 841(a)(1). In calculating Esteras’s
Guidelines range, the PSR recommended the application of several sentencing
enhancements. Specifically, the PSR determined that Esteras had used his
residence “for the purpose of manufacturing or distributing” fentanyl, which
triggered a two-level enhancement under U.S.S.G. § 2D1.1(b)(12). The PSR also
added two criminal history points under U.S.S.G. § 4A1.1(d) after determining
that Esteras was on parole when he committed his offenses.
Esteras objected to both of these enhancements at his sentencing, arguing
(1) that the “maintain[ing] a premises” enhancement under section 2D1.1(b)(12)
did not apply because he lived in the residence with his wife and children and
therefore did not use it primarily for drug trafficking, and (2) that the parole
violation enhancement under section 4A1.1(d) was inapplicable because he had
been discharged from parole the day before federal agents conducted the first
controlled buy from him. Separate from these enhancement challenges, Esteras
6 also argued that he was entitled to a two-level reduction in his offense level under
U.S.S.G. § 3B1.2(b) because he was only a “minor participant” in the conspiracy.
The district court rejected these arguments, adopted the factual information
contained in Esteras’s PSR, and determined that his Guidelines range was 84 to
105 months’ imprisonment. The court ultimately imposed concurrent 84-month
terms of imprisonment for Esteras’s two counts of conviction.
C. Frias’s Sentencing
Like Esteras, Frias pleaded guilty to one count of conspiring to distribute
and possess with intent to distribute a controlled substance, in violation of 21
U.S.C. §§ 841(a)(1) and 846, and one count of possession with intent to distribute a
controlled substance, in violation of 21 U.S.C. § 841(a)(1). Frias’s PSR applied a
two-level enhancement under section 2D1.1(b)(12) based on Frias’s use of his
mother’s residence for narcotics trafficking. It also applied a four-level
enhancement under U.S.S.G. § 3B1.1(a) due to Frias’s role as an “organizer or
leader” of a criminal scheme involving five or more persons.
At his sentencing, Frias objected to application of the “organizer or leader”
enhancement under section 3B1.1(a) but did not dispute the “maintain[ing] a
premises” enhancement under section 2D1.1(b)(12). He also asked for a three-level
7 downward variance due to his long history of childhood trauma and recent efforts
to get mental health treatment.
The district court rejected these arguments and adopted the PSR’s factual
findings and Guidelines calculation, concluding that Frias’s Guidelines range was
120 to 150 months’ imprisonment. The district court sentenced him to concurrent
135-month terms of imprisonment on the two counts of conviction.
II. DISCUSSION
Where a defendant has preserved a challenge to a sentencing enhancement,
we apply a mixed standard of review to assess whether the district court properly
applied the enhancement. See United States v. Si Lu Tian, 339 F.3d 143, 156 (2d Cir.
2003). We first review the district court’s factual findings for clear error, see id.,
which we will find only where the record as a whole leaves us “with the definite
and firm conviction that a mistake has been committed.” United States v. Cuevas,
496 F.3d 256, 267 (2d Cir. 2007) (internal quotation marks omitted). We then
review de novo the district court’s ultimate legal determination as to whether those
factual findings support an enhancement under the Guidelines. See Si Lu Tian, 339
F.3d at 156.
8 However, where the defendant failed to object at sentencing to the district
court’s application of an enhancement, we review for plain error. See United States
v. Ware, 577 F.3d 442, 452 (2d Cir. 2009). This requires the defendant to show (1)
that there was an “error,” (2) that is “clear or obvious,” (3) that “affected the
outcome of the district court proceedings,” and (4) that “seriously affects the
fairness, integrity[,] or public reputation of judicial proceedings.” United States v.
Marcus, 560 U.S. 258, 262 (2010) (alterations and internal quotation marks omitted).
On appeal, Esteras and Frias raise various challenges to their sentences,
arguing that the district court erred either by applying certain enhancements or by
failing to grant reductions. We address each challenge in turn.
A. Esteras’s Stash-House Enhancement Under Section 2D1.1(b)(12)
Esteras argues that the district court erred when it enhanced his offense level
pursuant to U.S.S.G. § 2D1.1(b)(12), otherwise known as the stash-house
enhancement. This provision calls for a two-level increase to the offense level
when “the defendant maintained a premises for the purpose of manufacturing or
distributing a controlled substance.” U.S.S.G. § 2D1.1(b)(12). As the Guidelines
commentary explains, the stash-house enhancement applies to any defendant who
(1) knowingly (2) maintains (3) a premises (such as a “building, room, or
9 enclosure”) (4) for the “purpose of manufacturing or distributing a controlled
substance, including storage of a controlled substance for the purpose of
distribution.” Id. § 2D1.1 cmt. n.17.
Though Esteras does not dispute that he knowingly maintained the
residence at issue here (which he rented at the time), he argues that the
enhancement cannot apply because the residence was a family home where he
lived with his wife and children. This presents a matter of first impression in our
Circuit, as we have not yet decided in a published opinion whether “a defendant’s
use of a premises as a home . . . categorically bar[s] application of the [stash-house]
enhancement.” United States v. Vinales, 78 F.4th 550, 553 (2d Cir. 2023).
We have little trouble rejecting Esteras’s argument that a family home can
never support an enhancement under section 2D1.1(b)(12). For starters, the
Guidelines commentary – which we generally treat as authoritative when
interpreting the Guidelines, see Stinson v. United States, 508 U.S. 36, 38 (1993) –
forecloses a categorical rule of that sort. Indeed, the commentary to the stash-
house enhancement explains that a premises can have more than one “primary”
or “principal” use. U.S.S.G. § 2D1.1(b)(12) cmt. n.17 (“Manufacturing or
distributing a controlled substance need not be the sole purpose for which the
10 premises was maintained, but must be one of the defendant’s primary or principal
uses for the premises, rather than one of the defendant’s incidental or collateral
uses for the premises.”). It is thus entirely possible for a dwelling to be
“primar[il]y” used as both a residence and a narcotics distribution point. That a
premises is used as a family home therefore does not categorically shield that
residence from triggering an enhancement under section 2D1.1(b)(12). To hold
otherwise would permit drug traffickers to “eva[de]” the enhancement by
distributing narcotics out of family dwellings – a wholly illogical result. County of
Maui v. Haw. Wildlife Fund, 590 U.S. 165, 178–79 (2020) (applying the general
presumption against interpreting statutes in a way that creates “a large and
obvious loophole”).
Nor are we the first circuit to reach this result. Indeed, every other court of
appeals to address this issue has likewise concluded that the use of a family
residence for trafficking activities can, depending on the circumstances, trigger the
stash-house enhancement. See United States v. Melendez-Rosado, 57 F.4th 32, 38 (1st
Cir. 2023); United States v. Gardner, 32 F.4th 504, 526 (6th Cir. 2022); United States v.
Zamudio, 18 F.4th 557, 562–63 (7th Cir. 2021); United States v. Galicia, 983 F.3d 842,
844 (5th Cir. 2020); United States v. Murphy, 901 F.3d 1185, 1190 (10th Cir. 2018);
11 United States v. George, 872 F.3d 1197, 1206 (11th Cir. 2017); United States v. Miller,
698 F.3d 699, 706–07 (8th Cir. 2012). We see no basis to doubt or depart from these
well-reasoned opinions, which looked (as we do here) to the commentary’s clear
command that a residence may be maintained for more than one primary purpose.
We must then decide whether, on the facts of this case, one of the primary
uses of Esteras’s home was to further narcotics trafficking. We resolve such
inquiries by examining the “totality of the circumstances” surrounding the drug
trafficking and the extent to which the residence was used to further that activity.
Vinales, 78 F.4th at 553 (quoting Murphy, 901 F.3d at 1191) (using a totality-of-the-
circumstances test to decide whether section 2D1.1(b)(12) applies); see also United
States v. McDowell, 804 F. App’x 38, 40 (2d Cir. 2020) (same). We do so by
considering factors such as (i) “the frequency and number of drug sales occurring
at the home,” (ii) “the quantities of drugs bought, sold, manufactured, or stored in
the home,” (iii) “whether drug proceeds, employees, customers, and tools of the
drug trade . . . [were] present in the home,” and (iv) “the significance of the
premises to the drug venture.” Murphy, 901 F.3d at 1191–92; see also Melendez-
Rosado, 57 F.4th at 39 (“Pertinent circumstances typically include the activities
observed, the quantity of drugs discovered, and the presence or absence of drug
12 paraphernalia and tools of the trade.”). In applying these factors, we defer to any
factfinding by the district court at sentencing that was not clearly erroneous, see
Cuevas, 496 F.3d at 267, and accept as true any facts in the PSR that were not
disputed by the defendant and were adopted by the district court, see Fed. R. Crim.
P. 32(i)(3)(A); United States v. Rizzo, 349 F.3d 94, 99 (2d Cir. 2003).
Applying that framework here, we see no error in the district court’s
conclusion that Esteras’s use of his home qualified for the stash-house
enhancement under section 2D1.1(b)(12). At sentencing, the district court adopted
the undisputed factual information in Esteras’s PSR and found that the trafficking
activity at his home was “certainly . . . sufficient and significant enough” to
warrant the enhancement. Esteras App’x at 67, 77. The undisputed facts bear out
that conclusion. For starters, Esteras stored substantial “quantities of drugs” at his
home, to the point that agents found sixty-six grams of fentanyl there on the day
of his arrest alone. Murphy, 901 F.3d at 1191; see also Drug Enf’t Admin., Facts About
Fentanyl (2024), https://www.dea.gov/resources/facts-about-fentanyl
[https://perma.cc/GP8X-67DY] (noting that “2 mg of fentanyl [is] considered a
potentially lethal dose”). This was no isolated instance, as Esteras’s PSR confirms
that he “routinely” used his home to “store and package fentanyl for
13 redistribution,” Esteras PSR ¶ 16 – a fact that Esteras admitted during his plea
colloquy. The investigation also yielded a recording in which Esteras told an
associate that he had been “bagging” fentanyl at the “crib” and servicing
customers “[a]ll day.” Esteras App’x at 26. And beyond the narcotics themselves,
agents also found “tools of the drug trade” in Esteras’s home, Murphy, 901 F.3d at
1191–92, including glassine envelopes used to distribute fentanyl and stamps used
to brand the envelopes as containing fentanyl, see Esteras PSR ¶ 23. Finally,
Esteras had no substantial source of legitimate income, bolstering the inference
that he supported himself by using his home as a trafficking hub. See United States
v. Winfield, 846 F.3d 241, 243 (7th Cir. 2017).
None of Esteras’s counterarguments are persuasive. He argues, for instance,
that his home could not qualify for the enhancement unless the government could
prove that it “was utilized more frequently for illegal activity than as the family
residence.” Esteras Br. at 9. But while the Guidelines commentary advises
sentencing courts to consider how “frequently” the property was used for
“lawful” versus unlawful uses, U.S.S.G. § 2D1.1 cmt. n.17, we cannot agree that
this requires a strict comparison whereby a dwelling cannot qualify as a stash
house if it was used legally more often than illegally. Indeed, that sort of inquiry
14 would be tantamount to a categorical rule that excludes family homes from the
enhancement, given that families use their main residences perpetually whereas
drug storage and sales are necessarily intermittent. See Miller, 698 F.3d at 707
(rejecting this argument because section 2D1.1(b)(12) was “surely intended to
deter the manufacture and distribution of illegal drugs in ‘crack houses’ where
children are being raised”). In our view, the enhancement calls for consideration
of additional factors beyond the rote frequency of usage, such as the level of
narcotics stored at or distributed from the home and whether tools of the trade
were found there.
Equally unpersuasive is Esteras’s argument that the enhancement cannot
apply because he used his residence less extensively than Frias used his mother’s
residence. A district court may apply the stash-house enhancement to multiple
defendants in the same drug conspiracy; section 2D1.1(b)(12) contains no one-per-
conspiracy limit. Regardless of what Frias did at his mother’s home, the
underlying facts support the district court’s conclusion that Esteras used his
residence for “sufficient and significant” trafficking activities, Esteras App’x at 67,
which were more than “incidental or collateral” uses of the home, U.S.S.G. § 2D1.1
15 cmt. n.17. We therefore affirm the application of this enhancement to Esteras’s
Guidelines calculation.
B. Esteras’s Minor Participant Adjustment Under Section 3B1.2(b)
Esteras next asserts that the district court erred in declining to apply a
downward adjustment to his base offense level under U.S.S.G. § 3B1.2(b) because,
according to Esteras, he was a “minor participant” in the criminal conduct.
Whether a defendant qualifies as a minor participant is a “highly fact-specific”
inquiry. United States v. Shonubi, 998 F.2d 84, 90 (2d Cir. 1993). Importantly, a
defendant bears the burden of establishing that he is entitled to this mitigating
adjustment, see United States v. Wynn, 37 F.4th 63, 67 (2d Cir. 2022), and we will
disturb the district court’s assessment only for clear error, see United States v. Soto,
959 F.2d 1181, 1187 (2d Cir. 1992).
After hearing arguments over Esteras’s role in the trafficking conduct, the
district court concluded that Esteras had not provided “sufficient evidence” to
establish that he played only a “minor” role. Esteras App’x at 67. Esteras
challenges that conclusion on appeal, arguing (among other things) that he had
only a “small number” of customers, that he had a different supplier than Frias,
and that he was generally part of an “independent” conspiracy and had no control
16 over Frias’s distribution activities. Esteras Br. at 13–15. But none of these
arguments compels a finding of clear error here. Even if he had a small number
of customers, and even if those were separate customers from Frias’s, Esteras still
admitted to being responsible for distributing at least 124 grams of fentanyl. That
drug weight was well above that of some of his coconspirators and even on par
with that of Frias, who admitted responsibility for distributing 132 grams. Nor
does it matter that Esteras and Frias generally had different suppliers and
customers. Esteras and Frias were charged as part of the same conspiracy, in
which they ran parallel distribution operations while also coordinating with one
another to supply each other’s customers if needed. We therefore see no reason to
question the district court’s conclusion that Esteras failed to establish his
entitlement to a minor role reduction.
C. Esteras’s Parole Offense Enhancement Under Section 4A1.1(d)
Esteras argues that the district court erred by assigning him two criminal
history points under former U.S.S.G. § 4A1.1(d), which applied when the
defendant “committed the instant offense while under any criminal justice
sentence, including probation [or] parole.” U.S.S.G. § 4A1.1(d) (2021). Before
analyzing that challenge, we note that section 4A1.1(d) has since been amended
17 and moved to section 4A1.1(e), with several changes that retroactively reduce the
Guidelines ranges of certain defendants. See U.S.S.G. app. C amend. 821
(narrowing new subsection (e) to apply only to offenders with more serious
criminal histories and reducing from two to one the criminal history points added
for defendants to whom the revised subsection applies). Esteras does not argue,
at least on appeal, that these changes should be applied retroactively to him. 1 We
therefore adjudicate his challenge based on “the version of the . . . Guidelines in
effect at the time of sentencing.” United States v. Hendricks, 921 F.3d 320, 331 n.51
(2d Cir. 2019).
Esteras’s argument hinges on the contention that he was discharged from
parole on May 19, 2021, exactly one day before federal agents first conducted a
controlled buy from him. But even if it is true that Esteras made the first controlled
sale on May 20, he admitted in his post-arrest interview in July 2021 that he had
received “30 to [40] bricks of fentanyl from his source of supply every week for the
1 While this appeal was pending, the district court purported to sua sponte reduce Esteras’s sentence under 18 U.S.C. § 3582(c), presumably in light of the retroactive amendments to section 4A1.1. The district court lacked jurisdiction to take such action during the pendency of this appeal, see United States v. Jacques, 6 F.4th 337, 342 (2d Cir. 2021), and eventually vacated its resentencing order in recognition of that fact. Because Esteras does not ask this Court for retroactive relief, we do not consider it here. Once the Clerk of Court issues the mandate for this appeal, the district court (or Esteras) is free to raise this issue again, as appropriate.
18 past year.” Esteras PSR ¶ 28. As the district court explained, “it [would] lack[] all
common sense to say that . . . Esteras was not involved in [the relevant conduct]
while he was on state parole supervision.” Esteras App’x at 73. Given Esteras’s
undisputed confession of this earlier criminal conduct, we do not see how the
district court’s conclusion could be clear error.
D. Frias’s Stash-House Enhancement Under Section 2D1.1(b)(12)
Turning to Frias, he first challenges the district court’s application of the
stash-house enhancement based on his use of his mother’s residence. Unlike
Esteras, however, Frias did not object to the district court’s application of this
enhancement at sentencing. We thus review his challenge for plain error. To
qualify as “plain,” an error must be “clear under current law.” United States v.
Whab, 355 F.3d 155, 158 (2d Cir. 2004) (internal quotation marks omitted). To that
end, “[w]e typically will not find such error where the operative legal question is
unsettled, including where there is no binding precedent from the Supreme Court
or this Court.” Id. (internal quotation marks omitted). Absent such controlling
precedent, we will notice plain error only in the “rare case” where the error was
“so egregious and obvious as to make the trial judge and prosecutor derelict in
19 permitting it, despite the defendant’s failure to object.” Id. (internal quotation
marks omitted).
Frias argues that the district court plainly erred in applying the
enhancement because he did not “maintain” the premises – his mother did. He
also contends that the residence was not primarily used for narcotics trafficking,
since he did not live there and merely used it “occasionally” to store fentanyl in a
drawer. Frias Br. at 16–17.
We cannot say that it was plain error for the district court to apply the stash-
house enhancement to his sentence. Indeed, the very fact that these questions are
unresolved – in that neither we nor the Supreme Court has foreclosed application
of the enhancement on facts like these – precludes reversal for plain error. See
Whab, 355 F.3d at 158. And Frias certainly falls short of showing that the alleged
error was “so egregious and obvious” that the district court was “derelict” in
applying the enhancement. Id. (internal quotation marks omitted). To the
contrary, there was certainly evidence – including facts in Frias’s PSR to which he
did not object – suggesting that Frias maintained the residence for a primary
purpose of narcotics trafficking. The Guidelines commentary makes clear that a
defendant can “maintain” a premises within the meaning of section 2D1.1(b)(12)
20 even if he does not own or have a possessory interest in it, so long as the defendant
sufficiently “controlled access to, or activities at, the premises.” U.S.S.G. § 2D1.1
cmt. n.17. At the very least, Frias arguably exercised such control over the
residence here, in that he “often stored fentanyl there,” Frias App’x at 98, regularly
conducted “hand-to-hand” drug transactions right outside the residence, Frias
PSR ¶ 15, and at times even directed his mother to retrieve and distribute the
stashed narcotics to his customers, see id.; Frias App’x at 116–18. Along similar
lines, the facts also suggested that Frias put his mother’s home to a primary use of
drug trafficking. He conducted daily drug deals from the home, including two
controlled purchases totaling more than twenty grams. Agents also uncovered
thirteen grams of fentanyl, along with “multiple bundles of glassine envelopes,”
at the residence immediately following Frias’s arrest. Frias PSR ¶¶ 13, 15, 26.
Because any error was far from plain, we affirm the application of this
enhancement to Frias’s Guidelines calculation.
E. Frias’s Variance Based On Mitigating Factors
Frias argues that the district court failed to adequately address his evidence
of mitigating circumstances and, as a result, erred in failing to grant him a
downward variance. “We entertain a strong presumption that the sentencing
21 judge has considered all arguments properly presented to him, unless the record
clearly suggests otherwise. This presumption is especially forceful when . . . the
sentencing judge makes abundantly clear that he has read the relevant
submissions and that he has considered the [section] 3553(a) factors.” United States
v. Negron, 524 F.3d 358, 361 (2d Cir. 2008) (alterations and internal quotation marks
omitted).
In his sentencing submission, Frias detailed a traumatic childhood in which
he regularly witnessed drug use and domestic violence by his parents. He also
identified steps he intended to take in order to address his mental health and
substance abuse problems. But we see nothing in the record that “clearly
suggests” the district court failed to consider this evidence in imposing Frias’s
sentence. Id. To the contrary, the district court expressly stated that it had
considered “all the pertinent information including . . . submissions by counsel,”
Frias App’x at 236, engaged in an extensive colloquy with counsel over Frias’s
plans to change his life, id. at 232–36, and at one point acknowledged the “trauma”
that Frias had experienced as a youth, id. at 233. It is “abundantly clear” that the
district court considered Frias’s mitigation evidence, and Frias falls well short of
establishing otherwise. Negron, 524 F.3d at 361.
22 F. Frias’s Organizer Or Leader Enhancement Under Section 3B1.1(a)
Finally, Frias disputes the district court’s decision to apply a four-level
enhancement under U.S.S.G. § 3B1.1(a) on the grounds that he was an “organizer
or leader” of criminal activity involving at least five persons. This provision sets
forth different enhancements depending on whether a defendant was an
“organizer or leader,” as opposed to a “manager or supervisor.” Compare U.S.S.G.
§ 3B1.1(a), with id. § 3B1.1(b). Organizers and leaders are generally distinguished
from lesser managers and supervisors based on the degree of control they exercise
over the enterprise. To that end, the commentary instructs courts to differentiate
between the two categories by examining several factors, including (1) “the
exercise of decision making authority,” (2) “the nature of participation in the
commission of the offense,” (3) “the recruitment of accomplices,” (4) “the claimed
right to a larger share of the fruits of the crime,” (5) “the degree of participation in
the planning or organizing of the offense,” (6) “the nature and scope of the illegal
activity,” and (7) “the degree of control and authority exercised over others.” Id.
§ 3B1.1 cmt. n.4. Notably, this provision does not require the defendant to have
led or organized five persons; it requires only that the criminal activity involved
five persons (or was “otherwise extensive”) and that the defendant was an
23 organizer or leader of at least one of them. See United States v. Gaskin, 364 F.3d 438,
466–67 (2d Cir. 2004) (internal quotation marks omitted); see also U.S.S.G. § 3B1.1
cmt. n.2 (“[T]he defendant must have been the organizer, leader, manager, or
supervisor of one or more other participants.”).
Ultimately, whether a defendant qualifies as an organizer or leader under
section 3B1.1(a) is a legal question that we review de novo. See United States v.
Wisniewski, 121 F.3d 54, 57–58 (2d Cir. 1997). In general, “[a] district court must
make specific factual findings, by a preponderance of the evidence, to support any
sentencing enhancement under the Guidelines.” United States v. Ahders, 622 F.3d
115, 119 (2d Cir. 2010) (internal quotation marks omitted). Though a district court
may also “adopt the findings in the presentence report,” that is sufficient only “if
those findings are adequate to support the sentence imposed.” Id. (emphasis
At sentencing, the district court did not make separate factual findings as to
the section 3B1.1(a) enhancement, and instead “adopt[ed] the factual information
and Guidelines applications” contained in Frias’s PSR. Frias App’x at 236. On that
basis, the court determined that Frias acted as an organizer or leader and imposed
a four-level enhancement under section 3B1.1(a).
24 Frias argues that the PSR’s findings were inadequate to classify him as an
organizer or leader. 2 Although the PSR concluded that Frias qualified for this
enhancement because he “instructed his mother and his sister to retrieve and
distribute fentanyl on his behalf,” Frias PSR ¶ 37, Frias insists that he enlisted his
mother’s and sister’s assistance only a handful of times, and that he did not pay
them or otherwise “enmesh[]” them into his trafficking activities, Frias Br. at 12.
In response, the government contends that we should also consider the fact –
which the district court apparently did not rely on – that Frias gave instructions to
several “subdistributors” (i.e., wholesale buyers) on how to package and distribute
the fentanyl that Frias sold them in bulk. Gov’t Br. at 77.
We agree with Frias that, based on the record, he did not qualify as an
organizer or leader under section 3B1.1(a). Frias was effectively an independent
middleman who sold fentanyl in bulk to several customers. Although Frias
operated in parallel with Esteras’s dealing operation, Frias possessed no “decision
making authority” over Esteras’s distribution activities, nor did he engage in any
significant “planning or organizing” of it. U.S.S.G. § 3B1.1 cmt. n.4. He simply
2Although Frias also argued below that his offense did not involve “five or more participants,” U.S.S.G. § 3B1.1(a), he does not raise that argument on appeal. See United States v. Quiroz, 22 F.3d 489, 490 (2d Cir. 1994) (“It is well established that an argument not raised on appeal is deemed abandoned.” (internal quotation marks omitted)).
25 bought fentanyl from his own supplier and, on occasion, helped supply Esteras’s
customers as necessary. It is true that, on three occasions, Frias turned to his family
members to assist when they were at the residence and Frias was unable to get
there in time to service a customer. But in each instance, his mother and sister
were unpaid, and there is no evidence suggesting that Frias directed them to be
home at certain times or otherwise exercised “control and authority” over when
or how they were to assist him in upcoming deals. Id. Nor did Frias exercise any
significant degree of control over the subdistributors. See id. Although he gave
them instructions on how to process the fentanyl he sold them, those directions
were consistent with information provided by a distributor to a customer and not
commands. See, e.g., Frias App’x at 112–14 (recounting Frias’s advice to break
down the fentanyl with a card); id. at 116 (summarizing similar advice to another
buyer). Nothing suggests that Frias had any “decision making authority” over
whom his buyers were to sell to, when or where they were to sell fentanyl, or how
much they should charge. U.S.S.G. § 3B1.1 cmt. n.4. Indeed, there was no division
of labor here; this was essentially a one-man wholesale operation in which Frias
called on Esteras and his family members for favors on rare occasions. Given the
level of “decision making authority,” “degree of participation in the planning or
26 organizing of the offense,” and “degree of control and authority exercised over
others,” we find that Frias’s activity did not rise to the level of an organizer or
leader.
Even though Frias was not a leader or organizer – and therefore not subject
to the four-level enhancement in section 3B1.1(a) – the question remains whether
he warrants a three-level enhancement under section 3B1.1(b) for acting as a
manager or supervisor. But that is a straightforward inquiry, as Frias conceded to
the district court “that he merely managed/supervised his mother/sister” and “is
responsible for the supervisory role he played in regard to his mother and sister.”
Frias App’x at 189–90 (Frias arguing at sentencing that section 3B1.1(b) should
apply instead of section 3B1.1(a)). Given that we may “treat statements in briefs
as binding judicial admissions of fact,” Frias cannot now dispute application of the
three-level enhancement under section 3B1.1(b). Purgess v. Sharrock, 33 F.3d 134,
144 (2d Cir. 1994); see also Hoodho v. Holder, 558 F.3d 184, 191 (2d Cir. 2009)
("Admissions by parties are not subject to judicial scrutiny to ensure the
admissions are fully supported by the underlying record.”). We thus find that
27 Frias acted as a manager or supervisor and is subject to a three-level enhancement
under section 3B1.1(b). 3
III. CONCLUSION
For the reasons stated above, we AFFIRM Esteras’s sentence and VACATE
and REMAND Frias’s sentence for further proceedings consistent with this
opinion.
3Of course, on remand the district court is not bound by the advisory Guidelines range and may impose whatever sentence it deems sufficient, but not greater than necessary, to meet the sentencing objectives of 18 U.S.C. § 3553(a). See United States v. Davis, 139 S. Ct. 2319, 2336 (2019); United States v. Sindima, 488 F.3d 81, 87 (2d Cir. 2007).