The United States Court of Appeals for the First Circuit vacated a defendant’s sentence due to the prosecutor’s breach of the parties’ plea agreement, and the Court ordered resentencing before a different judge.

Before the Court was the appeal of Hector Maldonado-Maldonado, who along with one of his cellmates, Miguel Santana-Aviles, was involved in an altercation with a guard at the Metropolitan Detention Center Guaynabo in Puerto Rico. The guard was conducting a routine lockdown procedure and realized Maldonado was not in his cell. After the guard called Maldonado to return to his cell, he noticed a contraband extra pillow, which he removed and walked out of the cell.

Maldonado ran back to his cell at that point and began yelling profanities at the guard. Upon arrival at the cell, Maldonado punched the guard in the face. Santana then grabbed the guard from behind and held his arms. Maldonado put the guard in a headlock and repeatedly punched the guard’s face, head, and neck. Other guards quickly arrived, pepper sprayed both prisoners, and restrained them. The guard sustained bodily injuries to the hand, face, and neck.

Maldonado and Santana were indicted and charged with assaulting, resisting, and impeding a federal officer. See 18 U.S.C. § 111(a)(1), (b). Maldonado entered into a plea agreement, but Santana proceeded to trial and received an 87-month prison sentence. 

The plea agreement provided for a Base Offense Level (“BOL”) of 10, a Total Offense Level (“TOL”) of 13, and reflected a sentencing range of 18-24 months. The agreement included a three-page stipulation of facts, which did not mention the guard having any trouble breathing or elaborate on Maldonado’s intent in putting the guard in a headlock.

The Presentence Investigation Report (“PSR”) contained markedly different calculations. The PSR applied a 14 point “aggravated assault” BOL and applied 13 points of enhancements as well as a three-point responsibility reduction for a TOL of 24. The PSR utilized facts alleged at Santana’s trial to conclude that Maldonado “strangled” or “attempt[ed] to strangle” the guard, which supported application of the “aggravated assault” guideline § 2A2.2(a), via the cross-reference at § 2A2.4(c)(1).

That conclusion allowed the application of three sentencing enhancements that were not available under the “impeding officers” guideline contemplated by the plea agreement. Specifically, the PSR applied six points for “Official Victim,” two points because the guard was “physically restrained,” and three points for “bodily injury,” which was calculated as two points under the plea agreement. Maldonado timely objected to the PSR.

The Government then filed a sentencing memorandum. In that filing, the Government also used testimony from Santana’s trial. It described Maldonado’s conduct as a “vicious assault” and stated that it was “paramount” to deter future “assaultive behavior” by Maldonado. Thus, the Government requested a sentence of 24 months, which was the upper range under the plea agreement.

At Maldonado’s August 4, 2022, sentencing hearing, the prosecutor deviated from the Guidelines calculations in the plea agreement and the Government’s own sentencing memorandum. The prosecutor sought the “aggravated assault” guideline and enhancements in the PSR. The U.S. District Court for the District of Puerto Rico agreed and adopted the PSR’s sentencing guideline in full and imposed a 78-month prison sentence, which was the upper end for a TOL of 24 and criminal history of III. Maldonado timely appealed.

On appeal, the Government conceded that a breach of the plea agreement occurred. The Court agreed that the prosecutor committed a “clear and obvious” breach by “advocating for a greater [‘serious bodily injury’] enhancement” and “the use of the aggravated assault guideline,” which “opened the door to other sentencing enhancements” not allowed under the impeding an officer guideline.

The Court noted that the Government is held to “the most meticulous standards of both promise and performance” in executing plea agreements. United States v. Riggs, 287 F.3d 221 (1st Cir. 2002). “Such standards require more than lip service to, or technical compliance with, the terms of a plea agreement.” United States v. Almonte-Nunez, 771 F.3d 84 (1st Cir. 2014). Not only are explicit repudiations of the terms of plea agreements prohibited but so are “end-runs around them.” United States v. Canada, 960 F.2d 263 (1st Cir. 1992). 

The Court found error in the prosecutor’s description of the assault as “extraordinary,” “heinous,” and “violent.” The First Circuit has held that the prosecution’s use of terms like “extraordinary” or “exceptional” “impermissibly signal[s]” that the defendant’s case falls outside the “guidelines’ heartland” or the “mine-run” of cases. United States v. Mojica-Ramos, 103 F.4th 844 (1st Cir. 2024). Thus, the Court concluded that the prosecutor’s language together with the explicit request for the “serious bodily injury” enhancement “undermined the very basis for the sentence contemplated by the parties in the plea agreement.”

Having found Maldonado met all four prongs of the plain error standard and was entitled to resentencing, the Court turned to the parties’ disagreement as to the remedy. Both parties agreed sentencing before a different judge was warranted. The Government argued that sentencing before a different judge was sufficient relief. Whereas, Maldonado also sought specific instructions that the District Court impose a sentence within the range provided by the guidelines in the plea agreement.

The Government said it would fulfill its obligations under the plea agreement and recommend an 18–24-month sentence. As Maldonado had already served 32 months, that recommendation would amount to a request for time served.

The Court rejected Maldonado’s argument that the breach entitled him to a specific sentence imposed by the District Court. United States v. Kurkculer, 918 F.2d 295 (1st Cir. 1990). “The obligation of specific performance of the plea agreement runs against the government, not the district court,” the Court stated. “Further, the plea agreement did not bind the district court to adopt the parties’ recommended sentencing range.” See Fed. R. Crim. P. 11(c)(1)(A)-(B).

Depriving the District Court of its discretion in sentencing is “an extraordinary remedy [that] is only to be considered in the very rarest of circumstances,” the Court explained. See Mojica-Ramos. Such circumstances were not present in Maldonado’s case.

Accordingly, the Court vacated Maldonado’s sentence and remanded for expedited resentencing before a different judge. See: United States v. Maldonado, 134 F.4th 32 (1st Cir. 2025).  

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