United States v. Ubiles-Rosario

United States Court of Appeals
For the First Circuit

No. 16-1493

UNITED STATES OF AMERICA,

Appellee,

v.

KENNETH R. UBILES-ROSARIO,
also known as Keneth R. Ubiles-Rosario,

Defendant, Appellant.

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

[Hon. Carmen Consuelo Cerezo, U.S. District Judge]

Before

Torruella, Thompson, and Barron,
Circuit Judges.

Linda Backiel on brief for appellant.
Rosa E. Rodríguez-Vélez, United States Attorney, Mariana E.
Bauzá-Almonte, Assistant United States Attorney, Chief, Appellate
Division, and Francisco A. Besosa-Martínez, Assistant United
States Attorney, on brief for appellee.

August 16, 2017
 THOMPSON, Circuit Judge. The defendant, Kenneth Ubiles-

Rosario (Ubiles),1 argues on appeal that the government breached

the plea agreement and that the sentence imposed by the district

court is procedurally and substantively unreasonable. After

careful consideration, we affirm.

BACKSTORY2

This case was precipitated by a violent and tragic

episode. It all started when Ubiles enlisted Héctor Negrón Mercado

(Negrón) to help him commit a robbery. The pair, with Ubiles

driving his car, intercepted a vehicle driven by Luis Aníbal

Torres-González (Torres), a local businessman known to frequently

carry large sums of money. With Torres stopped, Ubiles left his

car and approached Torres's vehicle, forced Torres to the passenger

seat, and drove to a secluded area near the edge of a cliff; Negrón

followed in Ubiles's car. Ubiles forced Torres from his vehicle

at gunpoint while Negrón pillaged the vehicle of Torres's money

and valuables. With the loot safely transferred to Ubiles's car,

1
Although Ubiles's surname is hyphenated in the record below,
his briefs on appeal omit the hyphen.
2
In this appeal from the sentence imposed following Ubiles's
guilty plea, we glean the relevant facts from the plea agreement,
the undisputed sections of the presentence investigation report
(PSR), and the transcripts of his change-of-plea and sentencing
hearings. See United States v. Lasalle González, 857 F.3d 46, 52
(1st Cir. 2017).

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Ubiles shot Torres in the head, killing him.3 Ubiles and Negrón

then fled the scene in the two vehicles, abandoning Torres's car

along the way.

A federal grand jury indicted Ubiles and Negrón on one

count of carjacking by shooting and killing Torres and one count

of discharging a firearm during a crime of violence. Ubiles agreed

to plead guilty to the carjacking count in exchange for the

prosecution's dismissal of the firearm count.

Under the agreement, the government and Ubiles

stipulated to use a total offense level of 39 for purposes of their

sentencing recommendations, even though both recognized that the

correct total offense level would have been 40 absent their

agreement. The parties also agreed to recommend to the district

court a sentence between 262 and 300 months, with Ubiles arguing

for a sentence at the low end of that range and the government

"reserv[ing] the right to allocute for a term of imprisonment up

to three hundred (300) months." Finally, the parties agreed that

neither side would seek a "variant sentence under 18 U.S.C.

§ 3553(a)" or any "further adjustments or departures to [Ubiles's]

total adjusted offense level."

Notwithstanding the agreement between the parties with

respect to sentencing recommendations, Ubiles acknowledged in the

3 The force of the blast caused the body to fall over the
cliff edge, where it was discovered later that day.

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plea agreement that "the sentence will be left entirely to the

sound discretion of the" district court and that the statutory

maximum penalty was life imprisonment. Additionally, the

government "reserve[d] the right to carry out its responsibilities

under guidelines sentencing." In particular, the plea agreement

provided that

the United States reserves the right: (a) to bring its
version of the facts of this case including its file and
any investigative files to the attention of the
probation office in connection with that office's
preparation of a [PSR]; (b) to dispute sentencing
factors or facts material to sentencing; [and] (c) to
seek resolution of such factors or facts in conference
with opposing counsel and the probation office.

During the change-of-plea colloquy, the magistrate judge

informed Ubiles that the district-court "[j]udge does not have to

follow the[] [sentencing] recommendations [in the plea agreement]

and retains authority to impose any sentence up to the maximum

allowed by law." Ubiles indicated that he understood.

In its sentencing memorandum, the government reiterated

that it "reserved the right [under the plea agreement] to ask for

a sentence of 300 months of incarceration." To that end, the

government then identified the pertinent § 3553(a) factors that,

in its view, "[w]arrant[ed] a [s]entence of 300 months of

[i]ncarceration." In particular, it noted the prevalence of gun

violence in Puerto Rico and the premediated, deliberate, and

violent nature of the offense. It explained why the crime

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"require[d] punishment of no less than 300 months." (Emphasis

added.) Finally, it concluded by "recommend[ing] that th[e]

[c]ourt sentence the defendant to serve a term of 300 months of

imprisonment." Ubiles did not object to any aspect of the

government's memorandum at any point between the date on which it

was filed and the sentencing hearing, which was held almost one

year later.

At the sentencing hearing, Ubiles turned to face

Torres's family, expressed his remorse, and asked for their

forgiveness. The prosecutor told the district court that the

government's recommendation of 300 months appropriately balanced

Ubiles's acceptance of responsibility and expression of remorse

with the severity of the crime. Torres's wife and one of his sons

then addressed the court. Torres's son "ask[ed] for all the weight

of the law and justice for our father." After the family members

spoke, the prosecutor told the district court: "We hope that Your

Honor will consider our recommendation and sentence the defendant

to 300 months."

In pronouncing sentence, the district court stated that

it had "reviewed the applicable advisory guideline calculations"

and "ha[d] considered all sentencing factors in 18 U.S. Code,

Section 3553(a)." The district court determined that the parties'

stipulation to use a total offense level of 39, instead of 40, was

"without any justification." Although the court explicitly

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considered Ubiles's age, his two young daughters, his employment

history, his diagnosis before the crime of major depressive

disorder, his lack of prior criminal history, and his history of

substance abuse, the court emphasized "the grave nature of this

offense and the circumstances, which reflect extreme cruelty on

the part of the defendant Ubiles towards the victim." The court

also stressed the need "to effectively provide deterrence and to

protect the public from further crimes by this defendant, and also

to provide just punishment." For these reasons, the court

sentenced Ubiles to a term of 365 months of imprisonment, which

the court deemed "sufficient but not greater than necessary to

meet [the] objectives of punishment and of deterrence in this

case."

After the district court imposed sentence, Ubiles

objected to the court's refusal to follow the parties' sentencing

recommendations. Ubiles also explained the reason why the parties

selected a total offense level of 39 instead of 40: By pleading

guilty, Ubiles had waived several important constitutional rights

and had spared Torres's family of the ordeal and anguish of sitting

through Ubiles's trial. The district court reiterated that it

deemed a total offense level of 40 to be appropriate.

After this exchange between defense counsel and the

district court, the prosecutor interjected that "[t]he Government

stands by, obviously, its recommendation of 300 months." After

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observing that the PSR also used a total offense level of 40,

rather than 39, the prosecutor clarified: "Obviously, we're not -

- we stand by our plea agreement, Your Honor. I'm not trying in

any way to breach that plea agreement. I just wanted that to be

clear for the record."

Dissatisfied with the prosecutor's effort to defend the

plea agreement, Ubiles stated that "the prosecution is not

following, is not advocating for that sentence and is in fact

breaching the plea agreement." The prosecutor responded: "[T]he

agreement to stipulate to a level 39 was all done by me. We stand

by that. . . . We've asked for 300 [months], we believe that's an

appropriate sentence." Ubiles shot back that "the prosecutor has

not in any way advocated for the 300 months and is backing away

from the plea agreement." The prosecutor once again disagreed:

I take issue with that, I have said several times
throughout the course of this sentence that I'm asking
the Court to impose a 300-month sentence; to say
otherwise is just dishonest. I've said here now, after
this Court has imposed sentence, three times, that that
is our recommendation, we stand by it.

Ubiles filed a motion for reconsideration of his

sentence, arguing that the district court "did not explain the

reasons for imposing the highest permissible sentence within the

higher Guidelines range" and that a sentence within the range

recommended by the parties would have been more appropriate than

the sentence imposed by the district court. With the motion for

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reconsideration still pending, Ubiles timely appealed from the

district court's imposition of sentence.

The court denied the motion for reconsideration in an

order that reiterated much of the court's analysis at the

sentencing hearing. The court also considered Ubiles's expression

of remorse at sentencing, but the court stated that it perceived

"shallow sincerity" as Ubiles spoke.4

ANALYSIS

Ubiles's arguments on appeal can be grouped into two

categories.5 First, he argues that the government breached the

plea agreement, both at the sentencing hearing and earlier in the

government's sentencing memorandum. Next, he argues that the

4
Several months later, Negrón, who pled guilty to one count
of aiding and abetting carjacking resulting in death by a firearm,
was sentenced by the same district-court judge to 144 months of
imprisonment. Ubiles seizes on the discrepancy between his
sentence and Negrón's to support his argument on appeal that the
district court failed to adequately explain the reasons for giving
him a 365-month sentence, and we'll get to that argument in a
moment.
5
Like most plea agreements, Ubiles's had a waiver-of-appeal
provision. But, because the sentence imposed by the district court
was in excess of the sentencing range set forth in the agreement,
Ubiles was not (to use the lingo of the waiver-of-appeal provision)
"sentenced in accordance with the terms, recommendations, and
conditions set forth in the Sentence Recommendation provisions of
th[e] Plea Agreement." Therefore, as the government acknowledges,
this appeal is not barred by the waiver-of-appeal provision of the
plea agreement. See United States v. Cortés-Medina, 819 F.3d 566,
568-69 (1st Cir. 2016).

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district court imposed a sentence that is both procedurally and

substantively unreasonable. We address each category in turn.

A. Breach of the Plea Agreement

Ubiles's principal argument on appeal is that the

government breached the plea agreement by paying lip service to

its obligation to recommend a sentence no higher than 300 months.

Because "[a] defendant who enters a plea agreement waives a panoply

of constitutional rights . . . , we hold prosecutors to the most

meticulous standards of both promise and performance" in the plea-

agreement context. United States v. Marín-Echeverri, 846 F.3d

473, 478 (1st Cir. 2017) (internal quotation marks omitted)

(quoting United States v. Almonte-Nuñez, 771 F.3d 84, 89 (1st Cir.

2014)). These strict standards "require more than lip service to,

or technical compliance with, the terms of a plea agreement." Id.

(quoting Almonte-Nuñez, 771 F.3d at 89); see also id. ("[W]e frown

on technical compliance that undercuts the substance of the

deal."); United States v. Quiñones-Meléndez, 791 F.3d 201, 204

(1st Cir. 2015) ("The government is barred not only from 'explicit

repudiation of the government's assurances' contained in a plea

agreement but also — 'in the interest of fairness' — from

undertaking 'end-runs around them.'" (quoting United States v.

Rivera-Rodríguez, 489 F.3d 48, 57 (1st Cir. 2007))). Instead, "a

defendant is entitled not only to the government's 'technical

compliance' with its stipulations but also to the 'benefit of the

- 9 -
bargain' struck in the plea deal and to the good faith of the

prosecutor." United States v. Matos-Quiñones, 456 F.3d 14, 24

(1st Cir. 2006) (citation omitted) (quoting United States v. Clark,

55 F.3d 9, 11 (1st Cir. 1995)); see also United States v. Frazier,

340 F.3d 5, 11 (1st Cir. 2003) ("[A]s in all contracts, plea

agreements are accompanied by an implied obligation of good faith

and fair dealing" (quoting United States v. Ahn, 231 F.3d 26, 35-

36 (D.C. Cir. 2000))).

There is, of course, "[n]o magic formula" for assessing

whether a prosecutor has complied with a sentencing recommendation

in a plea agreement. United States v. Gonczy, 357 F.3d 50, 54

(1st Cir. 2004). In the end, we examine the totality of the

circumstances, Marín-Echeverri, 846 F.3d at 478, to determine

whether "the prosecutor's 'overall conduct [is] . . . reasonably

consistent with making such a recommendation, rather than the

reverse,'" Gonczy, 357 F.3d at 54 (quoting United States v. Canada,

960 F.2d 263, 268 (1st Cir. 1992)).

But that's not the complete picture. Although

prosecutors undeniably have "a duty to carry out the obligations

[the government] has undertaken [in a plea agreement] in both

letter and spirit," they also, "as officers of the court, remain

bound by their corollary duty to provide full and accurate

information about the offense and the offender to the sentencing

court." Almonte-Nuñez, 771 F.3d at 86. And "a plea agreement may

- 10 -
not abridge" the "solemn obligation to provide relevant

information to the sentencing court." Id. at 90; see also United

States v. Miranda-Martinez, 790 F.3d 270, 274 (1st Cir. 2015).

This court has recognized that these twin obligations can sometimes

"pull in different directions." United States v. Cruz-Vázquez,

841 F.3d 546, 549 (1st Cir. 2016); see also United States v. Gall,

829 F.3d 64, 73 (1st Cir. 2016) (characterizing these two

obligations as "competing" in the circumstances of that case);

Almonte-Nuñez, 771 F.3d at 86 ("[T]hese dual obligations sometimes

require prosecutors to walk a fine line.").

In resolving this tension, "there is a material

difference between answering questions asked by a sentencing court

or bringing facts to the court's attention," on the one hand, and,

on the other, engaging in conduct that violates the terms of the

plea agreement, by, for example, "affirmatively supporting an

adjustment" to the guideline range when the plea agreement

"obligate[s] the government to refrain from arguing further

guideline adjustments." Almonte-Nuñez, 771 F.3d at 90 (internal

quotations omitted); see also Miranda-Martinez, 790 F.3d at 274

(explaining that, on the one hand, "'[t]he mere furnishing' of

facts concerning the background, character, and conduct of the

defendant 'gives us little pause'" (quoting United States v.

Saxena, 229 F.3d 1, 6 (1st Cir. 2000)), while, "[o]n the other

hand, we have acknowledged that certain factual 'omission[s],

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helpful to the defendant,' may be 'an implicit part of the bargain'

in a plea agreement" (quoting United States v. Yeje-Cabrera, 430

F.3d 1, 28 (1st Cir. 2005))). We look to "[t]he precise terms of

the plea agreement" at issue to "help resolve these competing

tugs." Miranda-Martinez, 790 F.3d at 275.

Within this framework, Ubiles identifies three actions

of the government that, in his view, collectively amount to a

breach of the plea agreement: (1) the prosecutor's refusal to

explain or defend the parties' agreement to use an adjusted total

offense level of 39, instead of 40, when the district court deemed

that aspect of the agreement to be "without any justification";

(2) the "aggravating and extraneous factors" relied upon by the

government; and (3) the request in the sentencing memorandum that

the district court impose a sentence of "no less than 300 months."

1. Standard of Review

At the outset, the parties dispute the governing

standard of review. Emphasizing that he objected at the sentencing

hearing to what he perceived to be the government's breach of the

plea agreement, Ubiles insists that we review de novo whether the

prosecutor breached the plea agreement. See Cruz-Vázquez, 841

F.3d at 548 ("Whether the government has breached its plea

agreement with [a defendant] presents a question of law, and our

review is de novo."). The government stakes out a contrary

position. Although it concedes that "[t]his [c]ourt has not

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explicitly determined [precisely] when a defendant must raise a

claim that the government is in breach of a plea agreement in order

to sufficiently preserve the issue for appeal," it argues, citing

our case law from the closing-argument context, that Ubiles failed

to preserve the issue because he "did not contemporaneously object

to the government's allocution or sentence recommendation at the

time of the prosecutor's remarks nor prior to the district court

imposing sentence," such that the issue must be assessed under the

plain-error standard. See United States v. Betancourt-Pérez, 833

F.3d 18, 23-24 (1st Cir. 2016) (subjecting unpreserved claim that

government breached plea agreement to plain-error review). Ubiles

counters that it makes no sense to impart the preservation standard

from the closing-argument context to the very different setting of

the government's breach of a plea agreement at a sentencing

hearing.

Wholly apart from this particular preservation tussle,

the government also argues that Ubiles failed to preserve any

allegation of breach based on the government's sentencing

memorandum because Ubiles did not object to any aspect of the

memorandum either before or during the sentencing hearing. But

Ubiles has a rejoinder to this argument, too: According to Ubiles,

"[o]bjection to a prosecution sentencing memorandum has never been

required and would make no sense," evidently because, in his view,

(1) it is "unwise to anticipatorily antagonize the prosecutor,"

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(2) "[p]rior to the hearing, one must count on the good faith of

the prosecution to perform with some degree of enthusiasm at the

hearing," and (3) the government's "failure to support a

[sentencing] recommendation does not occur in a single instant,

but is cumulative."

We need not, however, enter this fray. The government

maintains that, even under de novo review, Ubiles's claim fails

because the government did not breach the plea agreement. We agree

and therefore assume, favorably to Ubiles, that he preserved all

aspects of his claim that the government breached the plea

agreement.6 See United States v. Delgado-Flores, 777 F.3d 529,

529 (1st Cir. 2015) (employing this approach).

2. Existence of Breach

Ubiles first complains of the government's conduct at

the sentencing hearing. He argues that the prosecutor failed to

defend the agreed-upon sentencing range — by, for example, noting

Ubiles's strong prospects for rehabilitation or the benefits to

the government and Torres's family that flowed from Ubiles's

decision to plead guilty — when the district court rejected the

parties' agreement to a lower total offense level than the level

called for by the guidelines. Relying on Gonczy, Ubiles contends

that, although the prosecutor reiterated the government's 300-

6 In charting this course, we express no opinion on the
parties' preservation arguments.

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month recommendation several times at the sentencing hearing, "no

fair reading of the prosecutor's argument to the court would lead

an impartial observer to think that [he] thought [300 months] was

an adequate sentence." (Alterations in original) (quoting Gonczy,

357 F.3d at 54). He also insists that the prosecutor spent most

of his time at the sentencing hearing emphasizing Torres's status

in the community, the effect the crime had on the Torres family,

the "completely senseless and selfish" nature of the crime, and

Ubiles's actions immediately after the crime. We disagree.

The government's conduct in Gonczy is very different

from what the prosecutor did in this case. Under the plea

agreement in Gonczy, the government agreed to recommend a sentence

at the low end of the guidelines sentencing range (GSR) calculated

by the district court. 357 F.3d at 51. At the sentencing hearing,

after the court calculated a GSR of 70 to 87 months, id., the

prosecutor began her argument by recommending, consistent with the

plea agreement, a sentence of 70 months, id. at 53. But the

prosecutor never returned to that recommendation during the

remainder of her argument. See id. at 54. Instead, as we

explained, "[t]he initial recommendation . . . was undercut, if

not eviscerated, by the [prosecutor]'s substantive argument to the

district court." Id. After characterizing the defendant as the

"brains behind th[e fraudulent] operation" and explaining how the

fraud "ruined many lives," id. at 53, the prosecutor's sentencing

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argument culminated with the statement that "the defendant at a

minimum deserves what the guidelines provide for and those are his

just deserts [sic]," id. at 54. Therefore, contrary to its

obligation under the plea agreement to recommend a sentence at the

low end of the GSR, the prosecutor argued that the entire GSR —

which spanned 17 months — was the "minimum" amount of time for

which the defendant should be sentenced. Id. We agreed with the

district court's assessment of the prosecutor's argument: "that

'no fair reading of [the prosecutor's] argument to the [c]ourt

would lead an impartial observer to think that [she] thought 70

months' was an adequate sentence.'" Id. We concluded that the

prosecutor breached the plea agreement because, "[w]hile paying

lip service to a term of 70 months' imprisonment, the [prosecutor]

substantively argued for a sentence at the higher end of the

guidelines." Id.

Ubiles's case, by contrast, did not involve a lone

recommendation consistent with the plea agreement followed by

argument inconsistent with that recommendation, see id. at 53-54,

or, worse yet, a sentencing argument in which the prosecutor did

not even make the recommendation required by the plea agreement,

see Canada, 960 F.2d at 268-69 (finding breach of plea agreement

where prosecutor, despite acknowledging government's promise to

recommend only 36 months of incarceration, "never herself

affirmatively recommended a 36 month sentence and her comments

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seemed to undercut such a recommendation"; prosecutor's

"references to the agreement were grudging and apologetic," and

she "inject[ed] material reservations about the agreement to which

the government ha[d] committed itself"). Instead, in both the

sentencing memorandum and several times at the sentencing hearing,

the prosecutor explicitly recommended, consistent with the plea

agreement, a 300-month sentence. Cf. Rivera-Rodríguez, 489 F.3d

at 57 (distinguishing Canada because government asked court to

impose sentence it was entitled to recommend under plea agreement

"not once, but twice during the course of its argument").

After the district court rejected the parties' agreed-

upon total offense level of 39 as "without any justification" and

the back-and-forth discussion that ensued on that subject between

the court and defense counsel, the prosecutor, while acknowledging

that the PSR calculated a total offense level of 40, reiterated

that "[t]he Government stands by, obviously, its recommendation of

300 months " and further clarified that "we stand by our plea

agreement, Your Honor. I'm not trying in any way to breach that

plea agreement." Cf. Gall, 829 F.3d at 73 (concluding that there

was no breach of plea agreement where prosecutor, while

acknowledging that guidelines calculations in PSR — which were

different than parties' agreed-upon calculations — were correct,

nonetheless recommended a sentence reflecting calculations in plea

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agreement).7 Finally, when Ubiles protested, for the first time

in the case, that the prosecutor was breaching the plea agreement,

the prosecutor vigorously maintained (not once, but twice) that

the government was standing by its recommendation of 300 months.

In short, this case is very different from Gonczy. The

government stuck by its obligation under the plea agreement,

recommending the 300-month sentence that it was entitled to

recommend under the agreement early, often, and throughout the

sentencing in this case. And it "never explicitly or implicitly

sought" a sentence greater than 300 months. Cruz-Vázquez, 841

F.3d at 549.

Ubiles's gripe with the government's decision to

emphasize certain factors at the sentencing hearing — Torres's

status in the community, the impact the crime had on Torres's

family, the nature of the crime, and Ubiles's actions immediately

7 In a footnote in his opening brief, Ubiles asserts that "one
must count on the good faith of the prosecution to perform with
some degree of enthusiasm at the hearing." To the extent Ubiles
intended for this sentence to argue that the government in this
case breached the plea agreement because the prosecutor did not
perform with sufficient enthusiasm, any such argument is both (1)
not properly before us for lack of development, 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"), and (2) meritless, see
Almonte-Nuñez, 771 F.3d at 91 (explaining that prosecutor "was not
required to be effusive in refusing to support the adjustment");
Canada, 960 F.2d at 270 ("[A] prosecutor normally need not present
promised recommendations to the court with any particular degree
of enthusiasm . . . .").

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after committing the murder — is equally unavailing. The

government properly discussed the actions Ubiles took immediately

after the crime — going to the mall and having lunch — to rebut

Ubiles's expression of remorse at the sentencing hearing; although

the prosecutor "ha[d] no doubt the defendant is remorseful," he

stated that it was "important" for the court to "consider his

remorse on th[e] day" of the crime. See Almonte-Nuñez, 771 F.3d

at 87, 90 (holding that government did not breach plea agreement

where, although government was not requesting sentencing

enhancement for restraining victim, rebutted defense counsel's

assertion that discovery provided by government did not support

restraint enhancement by arguing that "the victim impact statement

furnished a factual basis for the two-level restraint

enhancement"; prosecutor's statement was "plainly made . . . to

correct what the [prosecutor] reasonably viewed as a misstatement

of fact by defense counsel"); see also Delgado-Flores, 777 F.3d at

531 (concluding that prosecutor did not breach plea agreement when

he discussed evidence that rebutted defense counsel's effort to

minimize defendant's role).

Nor is the government's sentencing-hearing reference to

the other factors troubling. "Having unequivocally [and

repeatedly] stated that it was recommending a sentence" of 300

months, "the government was free to offer reasons supporting its

recommendation," and that's precisely what the government did

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here. Cruz-Vázquez, 841 F.3d at 549; see also Rivera-Rodríguez,

489 F.3d at 58. Our decision in Almonte-Nuñez is illustrative.

At the sentencing hearing in that case, the government: (1)

characterized the robbery victim as "a defenseless female, 70 year

old woman, attacked in a way that nobody should have to face . . .

[w]hen she [was] sleeping, in a vulnerable state"; (2) referenced

"the vicious way that [the defendant] committed the crime, when he

assaulted [the victim] with no provocation"; and (3) chronicled

the "severe bodily injury" that the victim suffered as a result of

the crime. 771 F.3d at 90. Along the way, the prosecutor

repeatedly affirmed that the government was "standing by the plea

agreement." Id. We rejected the defendant's contention that the

government's sentencing argument amounted to a breach of the plea

agreement:

The Agreement allowed the prosecutor to seek the upper
end of the GSR contemplated by the Agreement, and the
[prosecutor] was within fair territory in emphasizing
facts that made a sentence at the low end of that GSR
inappropriate. The defendant admitted to committing a
heinous crime resulting in horrific injuries, and
nothing contained in the Agreement entitled him to have
the government sugarcoat the facts.

Id. at 91 (citation omitted).

So it is here. The government did not breach the plea

agreement by identifying evidence at the sentencing hearing that,

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in its view, supported the 300-month sentence that it was

requesting the district court to impose.8

In a somewhat related vein, Ubiles next argues that the

government breached the plea agreement by "advanc[ing] aggravating

factors" in its sentencing memorandum. In particular, Ubiles

highlights the following factors identified in the memorandum: (1)

statements contained in the PSR that Ubiles made to the probation

officer about Ubiles's role as the "mastermind" of the offense;

(2) statements not contained in the PSR or in the statement of

facts accompanying the plea agreement that Negrón made to law-

enforcement officers about what he and Ubiles did immediately after

the crime; and (3) the prevalence of gun violence in Puerto Rico.

Ubiles argues that these factors were not consistent with the

section of the plea agreement in which the government reserved the

right "to dispute sentencing factors or facts material to

sentencing" because that provision of the agreement did not permit

8
Ubiles also appears to criticize the prosecutor for allowing
Torres's family to speak. But the prosecutor did not breach the
plea agreement by allowing Torres's family to address the court,
something that he was legally required to do. See United States
v. Aguirre-González, 597 F.3d 46, 51 (1st Cir. 2010) (explaining
that the Crime Victims' Rights Act "enshrines a panoply of crime
victims' 'rights,' including rights 'to be reasonably heard at any
public proceeding in the district court involving . . .
sentencing,'" "obligates district courts in criminal proceedings
to 'ensure that the crime victim is afforded [such] rights' and
requires government prosecutors to 'make their best efforts to see
that crime victims are notified of, and accorded, the[ir] rights.'"
(alteration in original) (quoting 18 U.S.C. § 3771(a)(4), (b)(1),
(c)(1))).

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the government "to bring any and all relevant facts or argument to

the Court's attention at or before sentencing." Instead, Ubiles

contends that these aggravating factors were "calculated to

inspire an emotional response for retribution" and "to urge an

upward variance[] from established Guidelines levels." We reject

this argument.

For starters, Ubiles misapprehends the plea agreement.

We interpret plea agreements "in accordance with traditional

principles of contract law." Marín-Echeverri, 846 F.3d at 477-78

(quoting United States v. Marchena-Silvestre, 846 F.3d 196, 202

(1st Cir. 2015)). Contrary to Ubiles's assertion, the unambiguous

language of the reservation-of-rights paragraph in the plea

agreement does not prevent the government from bringing relevant

facts to the district court's attention. Although one provision

of this paragraph discusses the government's right "to bring its

version of the facts of this case . . . to the attention of the

probation office" (emphasis added), the other provisions of this

paragraph are not so limited. In particular, the government

reserved, without qualification, its "right to carry out its

responsibilities under guidelines sentencing" and its right "to

dispute sentencing factors or facts material to sentencing."

Therefore, the plea agreement did not bar the government from

bringing what it viewed as the relevant facts to the district

court's attention in connection with its sentence recommendation.

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This interpretation of the plea agreement recognizes that, "[b]y

statute, '[n]o limitation shall be placed on the information

concerning the background, character, and conduct of a person

convicted of an offense which a court of the United States may

receive and consider for the purpose of imposing an appropriate

sentence.'" Cruz-Vázquez, 841 F.3d at 549 (quoting 18 U.S.C.

§ 3661); see Almonte-Nuñez, 771 F.3d at 86 ("We repeatedly have

emphasized that prosecutors have a concurrent and equally solemn

obligation to provide relevant information to the sentencing court

and that a plea agreement may not abridge that obligation.").

And there was nothing sinister about the government's

decision to highlight certain facts and factors in its sentencing

memorandum.9 As was true at the sentencing hearing, the

government's reference to these sentencing factors was firmly

grounded in its recommendation that the court impose a 300-month

sentence, and the government was permitted to marshal the facts

and factors that, in its view, warranted the recommended sentence.

See Cruz-Vázquez, 841 F.3d at 549; Almonte-Nuñez, 771 F.3d at 91;

9 Ubiles asserts, in passing, that some of the facts contained
in the government's sentencing memorandum were "not disclosed in
the PSR and not part of the Statement of Facts" accompanying the
plea agreement. However, apart from his meritless argument that
the terms of the plea agreement prohibited the government from
bringing these facts to the district court's attention, Ubiles
makes no attempt to develop an argument that the government's
reliance on facts not disclosed in the PSR was somehow improper.
Therefore, we need not consider any such undeveloped argument.
See Zannino, 895 F.2d at 17.

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Gonczy, 357 F.3d at 53 ("The government's review of the facts of

the case and of Gonczy's character cannot constitute a breach of

the plea agreement as they were relevant to the court's imposition

of the sentence; no limitation can be placed, by agreement or

otherwise, on this information."). Therefore, this aspect of the

sentencing memorandum was fully consistent with both the terms of

the plea agreement and the government's separate "duty to disclose

information material to the district court's sentencing

determinations." Cruz-Vázquez, 841 F.3d at 548-49.

Finally, Ubiles's reliance on the "no less than 300

months" language of the government's sentencing memorandum cannot

carry the day.10 Initially, we note that, although Ubiles now

challenges this phrase as a breach of the plea agreement, he voiced

no complaint relating to this phrase either at the sentencing

hearing or in the almost one year that elapsed between the filing

of the memorandum and the sentencing hearing. Cf. Miranda-

Martinez, 790 F.3d at 275 (explaining that absence of objection

from defense counsel "was not a mistake by counsel in the face of

plain breach, but was instead a recognition by competent counsel

10Throughout his opening and reply briefs, Ubiles insinuates
that the prosecutor requested a sentence of "at least" 300 months.
Ubiles has not pointed us to where in the record the prosecutor
requested a sentence of "at least" 300 months, and our independent
review of the record has revealed no support for that insinuation.

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that the agreement was not being breached at all").11 Additionally,

the phrase "not less than 300 months" is not literally inconsistent

with the prosecution's plea-agreement obligation to recommend a

sentence up to 300 months: Read literally, it suggests that

anything less than 300 months — the sentence that the government

twice recommended in the sentencing memorandum — was not

appropriate. Cf. Almonte-Nuñez, 771 F.3d at 91 (explaining, where

plea agreement allowed government to seek sentence at high end of

GSR, that prosecutor "was within fair territory in emphasizing

facts that made a sentence at the low end of that GSR

inappropriate"). Finally, even if this isolated phrase was

somewhat inartful, the government made crystal clear at sentencing

that it was standing by the agreement and recommending a 300-month

sentence; the government repeatedly reiterated this position, even

when the district court suggested that the parties' agreement on

a total offense level of 39 was not justified, see Saxena, 229

F.3d at 7 (explaining, in finding that government did not breach

plea agreement: "Perhaps most important, [the prosecutor]

resolutely stood by the bottom-line recommendation that the

government had committed to make . . . even after the court had

11
In making this observation, we by no means backtrack from
our decision to assume, favorably to Ubiles, that all of his breach
arguments have been preserved. See supra Part A.1. We simply
juxtapose Ubiles's current claim that three words in the
government's sentencing memorandum constitute a breach of the plea
agreement with his continued silence on that point below.

- 25 -
indicated that it would not" follow the parties' sentencing

recommendations), and the prosecutor vehemently denied defense

counsel's charge that the government was breaching the plea

agreement. Viewing the totality of the circumstances, as we are

required to do, see Marín-Echeverri, 846 F.3d at 478, we do not

perceive the government's use of this phrase to be a breach of the

plea agreement.

* * *

In sum, the plea agreement permitted the government to

recommend a 300-month sentence. The government did so, in both

its sentencing memorandum and at the sentencing hearing, and it

never wavered from that obligation, explicitly requesting a 300-

month sentence eight times. And, in recommending this sentence,

the government was entitled to explain the reasons why its

recommended sentence was appropriate. In the end, the government

never explicitly or implicitly sought a sentence higher than 300

months. Therefore, it did not breach the plea agreement.

B. The Sentence

Ubiles next contends that the sentence imposed by the

district court is both procedurally and substantively

unreasonable. We review the reasonableness of a sentence in a

bifurcated fashion, first assessing claims of procedural

unreasonableness before turning to plaints of substantive

unreasonableness. See Lasalle González, 857 F.3d at 61; United

- 26 -
States v. Arsenault, 833 F.3d 24, 28 (1st Cir. 2016). Generally

speaking, we "review both procedural and substantive

reasonableness under a deferential abuse-of-discretion standard."

Arsenault, 833 F.3d at 28. In the procedural-reasonableness

context, we apply the familiar abuse-of-discretion rubric in a

"multifaceted" manner: "'we afford de novo review to the

sentencing court's interpretation and application of the

sentencing guidelines, assay the court's factfinding for clear

error, and evaluate its judgment calls for abuse of discretion.'"

Id. (quoting United States v. Ruiz-Huertas, 792 F.3d 223, 226 (1st

Cir. 2015)).

This deferential manner of reviewing claims of

procedural reasonableness is altered, however, where the defendant

fails to preserve the claim of error in the district court; in

this circumstance, the daunting plain-error standard of review

supplants the usual abuse-of-discretion rubric.12 See Arsenault,

833 F.3d at 28; Vargas-García, 794 F.3d at 166.13 With this

12 To surmount the high plain-error hurdle, a defendant "must
show '(1) that an error occurred (2) which was clear or obvious
and which not only (3) affected the defendant's substantial rights,
but also (4) seriously impaired the fairness, integrity, or public
reputation of judicial proceedings.'" Lasalle González, 857 F.3d
at 62 (quoting United States v. Vargas-García, 794 F.3d 162, 166
(1st Cir. 2015)).
13 The consequence of a failure to lodge a substantive-
reasonableness objection in the district court is less clear.
"[T]he applicable standard of review for an unpreserved,
substantive reasonableness challenge is 'murky.'" Arsenault, 833
F.3d at 29 (quoting United States v. Pérez, 819 F.3d 541, 547 (1st

- 27 -
framework firmly in place, we turn to Ubiles's sentencing

arguments.

1. Procedural Reasonableness

On the procedural-reasonableness front, Ubiles claims

that the district court committed three procedural errors: (1)

improperly treating the guidelines as mandatory; (2) failing to

comply with the requirement of 18 U.S.C. § 3553(c)(1) that the

court explain its chosen sentence in open court; and (3) failing

to adequately explain the reasoning behind its chosen sentence of

365 months of imprisonment, especially given the fact that Negrón

subsequently received a sentence of only 144 months.14 We address

each claim of procedural error in turn.

Cir. 2016)); see also Ruiz-Huertas, 792 F.3d at 228 (noting that
it is unclear whether an unpreserved substantive reasonableness
claim should be reviewed for abuse of discretion or plain error).
In this case, both parties urge us to definitively decide the
question of which standard of review applies, and, unsurprisingly,
the parties stake out competing positions. We decline this
invitation, however. Because Ubiles's substantive-reasonableness
challenge fails under the more defendant-friendly abuse-of-
discretion rubric, we apply that standard, leaving for another day
the task of definitively resolving this lingering question. See,
e.g., Arsenault, 833 F.3d at 29 (steering this course).
14 Ubiles appears to offer his second and third claims as
distinct procedural errors, so we shall treat them separately.
Additionally, the parties squabble over whether Ubiles's motion
for reconsideration — filed the day after sentence was imposed —
was sufficient to preserve these two claims of procedural error in
the absence of an objection during the sentencing hearing. Because
it makes no difference to the outcome, we assume, favorably to
Ubiles, that he preserved these claims. See United States v.
Vazquez-Martinez, 812 F.3d 18, 25 (1st Cir. 2016) (employing this
approach).

- 28 -
 In his first claim of procedural error, Ubiles argues

that the district court treated the guidelines as mandatory. See

Gall v. United States, 552 U.S. 38, 51 (2007) (characterizing such

an error as procedural error). The record demonstrates

definitively that no such error occurred. Before pronouncing

sentence, the district court stated that it had "reviewed the

applicable advisory guideline calculations." (Emphasis added.)

See United States v. Ofray-Campos, 534 F.3d 1, 38 (1st Cir. 2008)

(rejecting claim that district court treated guidelines as

mandatory where court stated that it was "using the guidelines as

advisory"; "There is no doubt, therefore, that the district court

imposed the sentence under the correct understanding that the

sentencing guidelines are advisory, not mandatory").

Entirely ignoring this passage of the sentencing-hearing

transcript, Ubiles contends that the court's rejection of the

parties' agreed-upon total offense level as without justification

"betray[ed] continuing reflexive reliance upon pre-Booker law and

practice common in the District of Puerto Rico." But, as Ubiles

acknowledged in the plea agreement, at his change-of-plea

colloquy, and on appeal, the district court was not bound by the

parties' agreement, and the mere fact that the court declined to

follow the agreed-upon total offense level (and instead used the

concededly correct total offense level in its guidelines

- 29 -
calculations) does not erase the court's explicit acknowledgement

of the advisory nature of the guidelines.

Ubiles next argues that the district court did not comply

with 18 U.S.C. § 3553(c)(1) because it failed to explain, in open

court, the reasons for the sentence it imposed. "A sentencing

court must 'state in open court the reasons for its imposition of

the particular sentence.'" Lasalle González, 857 F.3d at 62

(quoting § 3553(c)). Section 3553(c) requires an in-court adequate

explanation for the imposed sentence "to allow for meaningful

appellate review and to promote the perception of fair sentencing."

Vargas-García, 794 F.3d at 166 (quoting Gall, 552 U.S. at 50).

Contrary to Ubiles's claim, however, the district court

did explain its reasons for the sentence in open court during the

sentencing hearing. The court's subsequent order denying Ubiles's

motion for reconsideration — which Ubiles appears to view as the

first articulation of the district court's reasons — largely

repeats what the district court said at the sentencing hearing.

The only arguably "new" reason offered in the order was the court's

assessment of Ubiles's "shallow sincerity" when he apologized to

Torres's family.15 Therefore, because the district court stated

15A brief detour on the district court's "shallow sincerity"
assessment: In his opening brief, Ubiles, while acknowledging
that this court is not in the business of second-guessing
credibility assessments made by a sentencing judge, notes that the
district court was not facing Ubiles when he spoke to the family
and that the prosecutor, who evidently was facing him, expressed

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its reasons in open court as required by § 3553(c), we reject

Ubiles's argument to the contrary.

The last arrow in Ubiles's procedural-error quiver is

his contention that the district court's explanation for its 365-

month sentence was inadequate. According to Ubiles, the district

court failed to consider all of the § 3553(a) factors. Ubiles

also thinks that the disparity between the 144-month sentence that

Negrón received and the 365-month sentence imposed on Ubiles makes

the district court's brief explanation of its reasons all the more

suspect.

Contrary to Ubiles's protestations, the district court's

explanation easily passes muster. A sentencing court "need not be

'precise to the point of pedantry'" in its explanation; instead,

the "'court need only identify the main factors behind its

decision.'" Lasalle González, 857 F.3d at 62-63 (quoting Vargas-

García, 794 F.3d at 166). The court's explanation in this case

meets this benchmark. For starters, the court explicitly stated

no doubt about the sincerity of Ubiles's remorse. He goes a step
further in his reply brief, noting that this court can set aside
a district court's credibility findings in some circumstances and
arguing that, because Ubiles repeated his apology multiple times,
"it has the ring of sincerity." But "[i]t is for the sentencing
court to assess the credibility of [a] witness, and it is for the
appellate court to defer to that assessment unless it is clearly
erroneous." United States v. Ortiz-Torres, 449 F.3d 61, 78 (1st
Cir. 2006). Ubiles falls far short of establishing that the
district court's assessment of his sincerity was clearly
erroneous. Thus, to the extent Ubiles means to challenge this
credibility assessment, we are unmoved.

- 31 -
that it had "considered all sentencing factors in" § 3553(a), and

"such a statement is entitled to some weight." Arsenault, 833

F.3d at 32 (quoting Ruiz-Huertas, 792 F.3d at 226-27). And it

expressly weighed several of these factors on the record at the

sentencing hearing.

The court considered the defendant's age, education and

employment history, recent diagnosis of mental illness, lack of

criminal record, and his two young daughters. See 18 U.S.C.

§ 3553(a)(1) (identifying as a sentencing factor "the history and

characteristics of the defendant"). The district court also

considered "the nature and circumstances of the offense," id., in

detail. In particular, the district court characterized the nature

of the offense as "grave," and explained that the circumstances

"reflect[ed] extreme cruelty on the part of the defendant Ubiles

towards the victim." Additionally, the court stressed the need

"to effectively provide deterrence and to protect the public from

further crimes by this defendant, and also to provide just

punishment." See id. § 3553(a)(2)(A)-(C) (specifying these

sentencing factors).16 Based on the court's balancing of these

sentencing factors, the court stated that a 365-month sentence "is

sufficient but not greater than necessary to meet [the] objectives

16 In addition, the court explicitly considered the advisory
GSR, see 18 U.S.C. § 3553(a)(4)(A), and the need for Ubiles to pay
restitution to the Torres family, see id. § 3553(a)(7).

- 32 -
of punishment and of deterrence in this case." See id. § 3553(a)

("The court shall impose a sentence sufficient, but not greater

than necessary . . . .").

Although "a district court is obliged to 'consider all

relevant section 3553(a) factors, it need not do so mechanically,'"

Ruiz-Huertas, 792 F.3d at 226 (quoting United States v. Clogston,

662 F.3d 588, 592 (1st Cir. 2011)), by, for example, "address[ing]

those factors, one by one, in some sort of rote incantation when

explicating its sentencing decision," id. (quoting United States

v. Dixon, 449 F.3d 194, 205 (1st Cir. 2006)). Where, as here,

"the record permits a reviewing court to identify both a discrete

aspect of an offender's conduct and a connection between that

behavior and the aims of sentencing, the sentence is sufficiently

explained to pass muster under section 3553(c)." Vargas-García,

794 F.3d at 166 (quoting United States v. Fernández–Cabrera, 625

F.3d 48, 54 (1st Cir.2010)).17

The discrepancy between Ubiles's 365-month sentence and

Negrón's 144-month sentence does not alter this conclusion.18 As

17 Ubiles also appears to attack the adequacy of the court's
explanation by highlighting the lack of extended explanation for
disregarding the parties' recommended total offense level and GSR.
This argument is a nonstarter. "[A]lthough a district judge has
a duty to adequately explain [her] choice of a particular sentence,
'[she] has no corollary duty to explain why [she] eschewed other
suggested sentences.'" Arsenault, 833 F.3d at 32 (quoting Ruiz–
Huertas, 792 F.3d at 228).
18Although § 3553(a)(6) lists "the need to avoid unwarranted
sentence disparities among defendants with similar records who

- 33 -
Ubiles acknowledges in his brief, he and Negrón are hardly

similarly situated. Although both participated in the crime,

Ubiles clearly took the laboring oar in this carjacking: he

conceived the plan, enlisted Negrón to assist him, used his car to

impede the path of travel of Torres's vehicle, forced Torres to

the passenger seat, drove Torres's car to a secluded area, directed

him at gunpoint to the edge of a cliff, and shot Torres in the

head and killed him. In short, given the different roles that

Ubiles and Negrón played in this tragic saga, it was by no means

unreasonable to sentence them differently. Cf. Arsenault, 833

F.2d at 33-34 n.5 (rejecting sentencing-disparity challenge where

defendant "proffer[ed] no evidence that the [other offenders]

cited were in fact identically situated to him").19

Discerning no procedural error, we now turn to Ubiles's

claim that his sentence is not substantively reasonable.

have been found guilty of similar conduct" as a sentencing factor
that may be relevant, Ubiles clarifies in his reply brief that he
is not making an argument about "unwarranted disparity."
Therefore, we consider Ubiles's reference to Negrón's sentence to
be a part of his larger argument that the district court failed to
adequately explain the reasons for its chosen sentence.
19We emphasize that this conclusion is dictated by our highly
deferential standard of review and our sentence-disparity
precedent. Even though there are significant differences between
Ubiles and Negrón, they both actively participated in this crime,
and we are somewhat baffled by the 221-month gulf between their
respective sentences. Ultimately, however, because the district
court adequately explained the sentence it imposed on Ubiles, we
must reject Ubiles's argument about the adequacy of the
explanation.

- 34 -
 2. Substantive Reasonableness

Ubiles's substantive-reasonableness challenge — in which

he argues that the district court abused its discretion by focusing

only on the nature of the offense, the deterrent and punitive

objectives of sentencing, and the maximum sentence suggested by

the guidelines to the exclusion of factors favorable to Ubiles —

fares no better. Although he emphasizes the sentencing balance

that the parties struck in the plea agreement, the district court

was not bound by the parties' recommendations. See Gall, 829 F.3d

at 75. Instead, it was obligated to impose a sentence that was

reasonable.

Reasonableness in this context is not a static concept:

"[i]n most cases, there is not a single appropriate sentence but,

rather, a universe of reasonable sentences." Lasalle González,

857 F.3d at 63 (alteration in original) (quoting United States v.

Rivera-González, 776 F.3d 45, 52 (1st Cir. 2015)). At bottom,

"[a] sentence is substantively reasonable if the court gives a

'plausible rationale' and reaches 'a defensible result.'" Id.

(quoting United States v. Díaz-Arroyo, 797 F.3d 125, 129 (1st Cir.

2015)). Both hallmarks of a substantively reasonable sentence are

present in this case.

First, the sentencing court's rationale was plausible.

Although Ubiles characterizes the court's reasoning as

"conclusory," this label is simply inapt. As we explained above,

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the district court's reasoning appropriately stressed the

seriousness of Ubiles's crime and the need for the sentence imposed

to provide just punishment, deterrence, and protection of the

public. See Vargas-García, 794 F.3d at 167. As he did before the

district court, Ubiles stresses to us certain mitigating factors:

the unlikelihood that he will recidivate, based on his age upon

release; his employment history; and his relationships with his

family and the community. But "a sentencing court is entitled to

conduct an appropriate triage and weigh some factors more heavily

than others." Id. That occurred in this case.

Similarly, the district court reached a defensible

result. The district court explicitly determined that its sentence

satisfied the so-called "parsimony principle" — that a sentence be

"'sufficient, but not greater than necessary' to achieve the

legitimate goals of sentencing." Id. (quoting 18 U.S.C.

§ 3553(a)). And, given the heinous nature of this crime and the

statutory maximum penalty of life imprisonment, it was reasonable

for the district court to determine that a 365-month sentence was

appropriate.

THE END

For these reasons, we conclude that the government did

not breach the plea agreement and that the sentence imposed by the

district court was neither procedurally nor substantively

unreasonable. Therefore, we affirm the judgment below.

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