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United States v. Ubiles-Rosario

United States Court of Appeals, First Circuit

August 16, 2017

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


          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.

          Before Torruella, Thompson, and Barron, Circuit Judges.


         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.


         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, 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 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 "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 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 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 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]


         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 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 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 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 ...

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