United States v. Milan-Rodriguez , 819 F.3d 535 ( 2016 )

United States Court of Appeals
For the First Circuit
Nos. 15-1233, 15-1235
UNITED STATES OF AMERICA,
Appellee,
v.
JONATHAN MILÁN-RODRÍGUEZ,
Defendant, Appellant.
APPEALS FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF PUERTO RICO
[Hon. José Antonio Fusté, U.S. District Judge]
Before
Barron, Circuit Judge,
Souter,* Associate Justice,
and Selya, Circuit Judge.
Elizabeth Billowitz on brief for appellant.
Rosa Emilia Rodríguez-Vélez, United States Attorney, Nelson
Pérez-Sosa, Assistant United States Attorney, Chief, Appellate
Division, and Francisco A. Besosa-Martínez, Assistant United
States Attorney, on brief for appellee.
April 22, 2016
* Hon. David H. Souter, Associate Justice (Ret.) of the
Supreme Court of the United States, sitting by designation.
BARRON, Circuit Judge. Jonathan Milán-Rodríguez
("Milán") challenges his two, concurrent 168-month prison
sentences for his convictions on one count of conspiring to
distribute cocaine and one count of possessing a firearm while
being an unlawful user of a controlled substance. We affirm the
sentence for the drug conspiracy count, but we vacate the sentence
for the firearm count because it exceeds the statutory maximum
penalty for that count.
I.
The initial indictment in this case charged Milán with
one count of conspiring with forty-three other defendants to
possess with intent to distribute a variety of controlled
substances in a number of Puerto Rico locations, including near an
elementary school, in violation of 21 U.S.C. §§ 841(a)(1), 846,
and 860. That count of the indictment specifically noted that
"some of the defendants would refer to Milán as the owner of the
heroin." Milán was also charged, in a separate count of the
indictment, with one count of conspiring with a large subset of
the other defendants to possess firearms in furtherance of a drug-
trafficking crime, in violation of 18 U.S.C. §§ 924(c), (o).
Authorities arrested Milán on August 6, 2014, after
Puerto Rico police officers responded to a tip about drug
trafficking activities and gunshots near a residence in Puerto
Nuevo, Puerto Rico. Officers saw Milán near the residence and saw
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him carrying a firearm. They then entered the residence (after
receiving written consent from the homeowner) and found marijuana,
cocaine, a loaded firearm, and extra ammunition. Milán later
confessed that he was the sole owner of the items found at the
residence. He was then charged, in a separate indictment, with
possessing a firearm while being an unlawful user of a controlled
substance, in violation of 18 U.S.C. §§ 922(g)(3) and 924(a)(2).
On October 15, 2014, Milán and the government signed a
plea agreement. Under the agreement, Milán pleaded guilty to the
drug conspiracy count charged in the first indictment and the
firearm count charged in the second indictment. He did not plead
guilty to the firearm count charged in the first indictment.1
In the plea agreement, Milán admitted that, from at least
2000 through 2012, he conspired with the other charged defendants
to possess with intent to distribute heroin, cocaine, cocaine base,
and marijuana within 1000 feet of a school in Puerto Rico. Milán
also acknowledged in the plea agreement that he acted as a "manager
and owner" of one of the heroin "brands" sold by the drug-
trafficking organization. Milán further admitted that he
"possessed firearms to protect the drug trafficking activities."
The plea agreement also contained a stipulation as to
drug weight. Milán admitted that he conspired to possess with
1 That count was then dismissed at Milán's sentencing hearing.
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intent to distribute "at least five (5.0) but less than fifteen
(15.0) kilograms of cocaine." Milán did not admit, however, to
conspiring to possess with intent to distribute any specific amount
of the other drugs that he admitted were involved in the
conspiracy. And so the calculation of the base offense level (and
thus the recommended sentencing range under the United States
Sentencing Guidelines) in the plea agreement was based on only the
amount of cocaine to which Milán admitted conspiring to possess
with intent to distribute.
The plea agreement also contained a waiver-of-appeal
provision. We thus begin by addressing whether that provision
bars us from considering the merits of Milán's challenges.2
II.
The government, quite understandably, does not argue
that the appeal waiver bars Milán from appealing his sentence on
the firearm count. The waiver-of-appeal provision in the plea
agreement reads: "The defendant knowingly and voluntarily waives
his right to appeal the judgment and sentence in this case,
provided that the defendant is sentenced in accordance with the
terms and conditions set forth in the Sentence Recommendation
2Because Milán was charged in two separate indictments, there
were technically two separate "cases" against him below. Milán
then pleaded guilty to counts from both cases pursuant to the same
plea agreement. On January 15, 2015, the District Court sentenced
him on both of those counts at once. Milán then filed a notice of
appeal in each case on February 2, 2015.
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provisions of this Plea Agreement." The Sentence Recommendation
provision for the firearm count reads: "[T]he parties agree to
recommend that the defendant be sentenced to serve a term of
imprisonment within the applicable guideline range, at a total
offense level of 12." The sentence that the District Court imposed
on the firearm count was 168 months of imprisonment and thus well
above the guideline range of 10-16 months that applies to a
defendant with an offense level of 12 who, like Milán, has a
criminal history category of I.
The government does argue, however, that the appeal
waiver bars consideration of Milán's challenges to the sentence on
the drug conspiracy conviction. Milán does not counter that the
District Court's failure to impose a sentence on the firearm
conviction "in accordance with the terms and conditions" of the
plea agreement makes the appeal waiver as a whole "a dead letter."
See United States v. Almonte-Nuñez, 771 F.3d 84, 89 (1st Cir. 2014)
(considering an appeal waiver with similar language and
determining that because the District Court did not sentence the
defendant "in accordance with the terms and conditions" of the
plea agreement with respect to two of three counts, "the waiver-
of-appeal clause d[id] not pretermit appellate review"). Milán
instead makes the more limited argument that the District Court
did not sentence him "in accordance with the terms and conditions"
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set out in the Sentence Recommendation provision for the drug
conspiracy count. We agree with Milán on this point.
The Sentence Recommendation provision for the drug
conspiracy count reads: "[T]he parties agree to recommend to the
Court that the defendant be sentenced to serve a term of
imprisonment at the lower end of the applicable guideline range,
at a total offense level of 35. That is, to 168 months if [Milán's
criminal history category] is 1." The government emphasizes that
Milán did receive the exact sentence mentioned in the Sentence
Recommendation provision: 168 months.
But after Milán signed the plea agreement and before he
was sentenced, the sentencing guidelines changed. The change
reduced the total offense level for the drug conspiracy count from
35 to 33 and thereby reduced the guidelines range that applied to
Milan from 168 to 210 months of imprisonment to 135 to 168 months
of imprisonment. United States Sentencing Commission, Guideline
Manual, Sentencing Table (Nov. 2014). The change thus exposed a
latent ambiguity in the appeal waiver. Was a sentence "in
accordance with the terms and conditions of the plea agreement"
one for a term of imprisonment of 168 months, which was "at the
lower end" of the old but no-longer-applicable guidelines range,
or one for a term of imprisonment of 135 months, which was "at the
lower end" of the new and now-applicable guideline range? Because
our precedent is clear that "any ambiguities should be resolved in
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favor of allowing the appeal to proceed," United States v.
Fernández-Cabrera, 625 F.3d 48, 51 (1st Cir. 2010), the appeal
waiver does not bar us from considering Milán's challenges to his
sentence for the drug conspiracy conviction.3
III.
Milán contends that the 168-month sentence he received
on the drug conspiracy conviction was both procedurally and
substantively unreasonable. It is not clear from the record that
Milán raised below the challenges that he now raises, but the
government does not ask us to review only for plain error. We
thus review the reasonableness of Milán's sentence for the drug
conspiracy conviction for abuse of discretion. See United States
v. Perretta, 804 F.3d 53, 56-57 (1st Cir. 2015); United States v.
Encarnación-Ruiz, 787 F.3d 581, 586 (1st Cir. 2015).
A.
Milán argues that the District Court committed
procedural error in two ways. He contends first that the District
Court failed to give due consideration to the sentencing factors
set out at 18 U.S.C. § 3553(a). He also contends that the District
Court emphasized factors that should not have been considered at
all. Those improper factors, according to Milán, were the judge's
3
This conclusion makes it unnecessary for us to consider
Milán's alternative argument: that the District Court did not make
clear at Milán's change-of-plea hearing that Milán was waiving his
right to appeal in pleading guilty pursuant to the plea agreement.
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false perception that Milán was attempting to conceal Milán's
criminal history and the judge's personal frustration with what
the judge perceived to be the leniency of the Puerto Rico criminal
justice system.
We first reject Milán's argument that the District Court
failed to consider the § 3553(a) factors. The District Court was
not required to "dissect every [such] factor . . . 'one by one, in
some sort of rote incantation, when explicating its sentencing
decision.'" United States v. Rivera-Clemente, 813 F.3d 43, 51
(1st Cir. 2016) (quoting United States v. Turbides–Leonardo, 468
F.3d 34, 40–41 (1st Cir.2006)). The District Court made express
its consideration of "the nature and circumstances of the offense"
and "the need for the sentence imposed . . . to reflect the
seriousness of the offense." See 18 U.S.C. §§ 3553(a)(1), (2).
Our review of the record satisfies us that the District Court gave
due consideration to the § 3553(a) factors in imposing a sentence
at the top of the applicable guideline range. See Rivera-Clemente,
813 F.3d at 51.
We also disagree with Milán's contention that the
District Court improperly based its sentence on an erroneous
perception that Milán had attempted to conceal his criminal history
from the District Court. The District Court did comment on the
fact that Milán, on the advice of counsel, declined to provide
probation with any information about his criminal history. The
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District Court did also state that Milán had "give[n] the
impression," during his allocution, that "this [wa]s the first
brush he ha[d] with the law." But the District Court made clear
that Milán had a right to withhold information about his criminal
history and that the District Court was not "taking [tha]t against
[Milán]."
Finally, our precedent forecloses Milán's final
challenge, which targets the District Court's statements at
sentencing expressing frustration with the Puerto Rico court
system. Milán relies on our statement in United States v. Flores-
Machicote, 706 F.3d 16, 21 (1st Cir. 2013), that the
"perceived . . . habitual leniency of the local courts . . . is
not, in and of itself, a relevant sentencing factor." But we
explained in Flores-Machicote that the District Court did not rely
on such a perception given "the district judge's focus on the
defendant's criminal history." Id. at 22. That focus, we
concluded, "unmistakably show[ed] that the judge gave
individualized attention to the defendant's situation." Id. at
22.
So, too, here. The District Court -- as in Flores-
Machicote -- went through each of Milán's encounters with the
justice system in detail before imposing the sentence. Moreover,
in Flores-Machicote the District Court relied on the prior arrests
to explain why it imposed a sentence that varied upwards from the
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guidelines range, while here it is not at all clear that the
District Court based its within-range sentence on anything other
than the extensive nature of the drug conspiracy, Milán's
substantial role in it, and the very favorable stipulation as to
drug quantity that he received. Finally, Milán makes no developed
argument that, to the extent that the District Court did base the
sentence on an individualized assessment of Milán's prior
encounters with law enforcement, the District Court erred in doing
so. See United States v. Zannino, 895 F.2d 1, 17 (1st Cir. 1990)
("[I]ssues adverted to in a perfunctory manner, unaccompanied by
some effort at developed argumentation, are deemed waived.").
B.
We also reject Milan's contention that, even though his
168-month prison sentence was within the range specified by the
guidelines, that sentence was nonetheless substantively
unreasonable. "A sentence is substantively reasonable so long as
it rests on a plausible sentencing rationale and exemplifies a
defensible result." United States v. Fernández-Garay, 788 F.3d 1,
6 (1st Cir. 2015) (internal quotation marks omitted).
Milán argues that the District Court should have given
more weight to Milán's "disadvantaged background" and the "ample
evidence of his non-violent role in the conspiracy." [Blue Br.
27]. But the fact "[t]hat the court chose to attach less
significance to certain mitigating circumstances than [Milán]
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thinks they deserved does not make his sentence substantively
unreasonable." United States v. Colón-Rodríguez, 696 F.3d 102,
108 (1st Cir. 2012). Milán admitted in the plea agreement to
acting as the "manager and owner" of heroin sold by the large-
scale drug-distribution conspiracy in which he participated, and
that the conspiracy operated for at least twelve years. In this
case, therefore, the decision to emphasize those aggravating
circumstances was properly a "judgment call" for the District Court
to make. United States v. Madera-Ortiz, 637 F.3d 26, 32 (1st Cir.
2011). We thus affirm the District Court's sentence on the drug
conspiracy count.
IV.
We now turn to the sentence for the firearm count. The
applicable statute, 18 U.S.C. § 924(a)(2), establishes a ten-year
maximum prison sentence for anyone convicted of possessing a
firearm while being an unlawful user of a controlled substance.
The District Court sentenced Milán to a 168-month -- or fourteen-
year prison term for his conviction for that crime. For that
reason, as both parties recognize, we must vacate the sentence for
the firearm count. See United States v. Vázquez-Larrauri, 778
F.3d 276, 293 (1st Cir. 2015); United States v. García-Ortiz, 528
F.3d 74, 85 (1st Cir. 2008).
The government, however, asks us to direct the District
Court to impose the statutory-maximum sentence of 120 months'
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imprisonment on remand. The government does so despite having
previously agreed in the plea agreement to recommend a sentence
"within the applicable guideline range, at a total offense level
of 12." The guideline range at that offense level for a defendant
in Milán's criminal history category, both at the time of the plea
agreement and now, is 10-16 months' imprisonment. U.S.S.G. ch. 5
pt. A.4
We have at times directed the imposition of a statutory-
maximum sentence on remand where the District Court originally
imposed a sentence above that maximum. E.g., Vázquez-Larrauri,
778 F.3d at 293; United States v. Almonte-Nuñez, 771 F.3d 84, 92
(1st Cir. 2014). Here, however, the sentencing transcript
indicates that neither the government nor Milán ever communicated
the specific recommendation as to the firearm sentence to the
District Court during the sentencing hearing. Instead, the
government simply recommended 168 months as to the drug conspiracy
count and then noted its recommendation that the two sentences be
served concurrently. Thus, we reject the government's request to
direct a sentence at the statutory maximum on remand. We instead
remand for the District Court to impose an "appropriate sentence"
accompanied by an "adequate[] expla[nation]." Gall v. United
States, 552 U.S. at 50; see García-Ortiz, 528 F.3d at 85.
4
The plea agreement itself reflects this calculation of the
appropriate guideline sentencing range.
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V.
For the foregoing reasons, we vacate Milán's sentence
for possessing a firearm while being an unlawful user of a
controlled substance and remand for resentencing on that
conviction. Otherwise, we affirm.
So Ordered.
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