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

(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

(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

- 2 - 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

(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.

- 3 - 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.

- 4 - 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,

(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"

- 5 - 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

- 6 - favor of allowing the appeal to proceed," United States v.

Fernández-Cabrera,

(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,

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

Encarnación-Ruiz,

(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

(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.

- 7 - 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,

(1st Cir. 2016) (quoting United States v. Turbides–Leonardo,

, 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

(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,

.

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

- 8 - 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,

(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."

. That focus, we

concluded, "unmistakably show[ed] that the judge gave

individualized attention to the defendant's situation."

.

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

- 9 - 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,

(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,

(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]

- 10 - thinks they deserved does not make his sentence substantively

unreasonable." United States v. Colón-Rodríguez,

(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,

(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,

(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,

(1st Cir. 2015); United States v. García-Ortiz,

, 85 (1st Cir. 2008).

The government, however, asks us to direct the District

Court to impose the statutory-maximum sentence of 120 months'

- 11 - 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,

; United States v. Almonte-Nuñez,

(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.

- 12 - 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.

- 13 -