FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF
PUERTO RICO [Hon. Carmen Consuelo Cerezo, U.S. District
Backiel on brief for appellant.
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.
Torruella, Thompson, and Barron, Circuit Judges.
THOMPSON, CIRCUIT JUDGE.
defendant, Kenneth Ubiles-Rosario (Ubiles),  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
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, Ubiles shot Torres in the head, killing
Ubiles and Negrón then fled the scene in the two
vehicles, abandoning Torres's car along the way.
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
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."
the agreement between the parties with respect to sentencing
recommendations, Ubiles acknowledged in the 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
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
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 "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.
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
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
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."
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.
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
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."
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.
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 reconsideration still pending, Ubiles timely
appealed from the district court's imposition of
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.
arguments on appeal can be grouped into two
categories. 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 district court imposed a sentence
that is both procedurally and substantively unreasonable. We
address each category in turn.
Breach of the Plea Agreement
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
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.
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)).
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 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 ...