Prosecutorial Breach of Plea Agreements by Advocating Unauthorized Sentencing Enhancements Requires Vacatur and Resentencing

Introduction

United States v. Maldonado-Maldonado, 1st Cir. No. 22-1650 (Apr. 11, 2025), addresses the boundaries of prosecutorial conduct at sentencing after a guilty plea. The appellant, Héctor Maldonado-Maldonado, pleaded guilty under a written agreement that stipulated a specific Sentencing Guidelines calculation and a recommended range of 18–24 months. At sentencing, however, the Assistant U.S. Attorney argued for enhancements—most notably a four-level “serious bodily injury” enhancement and related adjustments—that were unavailable under the parties’ agreed guideline. The First Circuit held that this advocacy breached the plea agreement, vacated the sentence under plain-error review, and remanded for resentencing before a different judge.

Key issues:

Whether a prosecutor’s argument for sentencing enhancements beyond those promised in a plea agreement constitutes a breach;
How plain-error review applies to an unobjected-to breach at sentencing;
The appropriate remedy when a breach is established.

Parties:

Appellant/Defendant: Héctor Maldonado-Maldonado
Appellee/Plaintiff: United States of America
District Judge below: Hon. Aida M. Delgado-Colón (D. P.R.)
First Circuit panel: Judges Gelpí, Lipez, and Rikelman (author)

Summary of the Judgment

The First Circuit concluded that:

The government conceded that its sentencing advocacy breached the plea agreement.
Under the plain-error standard, Maldonado demonstrated (1) an error, (2) clear and obvious, (3) affecting substantial rights, and (4) impairing the fairness or integrity of the proceedings.
The prosecutor’s argument for a four-level “serious bodily injury” enhancement—and related reliance on the “aggravated assault” guideline—went beyond the parties’ stipulated guideline and recommended range.
The breach entitled Maldonado to vacatur of his 78-month sentence and resentencing before a different district judge.

Analysis

1. Precedents Cited

The court relied on a line of First Circuit cases emphasizing strict enforcement of plea agreements:

United States v. Almonte-Núñez, 771 F.3d 84 (1st Cir. 2014): Prosecutors must meet “the most meticulous standards of both promise and performance.”
United States v. Canada, 960 F.2d 263 (1st Cir. 1992): Beyond explicit repudiation, “end-runs” around plea terms are forbidden.
United States v. Matos-Quiñones, 456 F.3d 14 (1st Cir. 2006): A defendant is entitled to the benefit of the plea bargain and good faith performance by the prosecutor.
United States v. Acevedo-Osorio, 118 F.4th 117 (1st Cir. 2024): Plain-error review applies if breach is not objected to at sentencing.
United States v. Kurkculer, 918 F.2d 295 (1st Cir. 1990): Equitable relief may include remand to impose a plea-range sentence only in rare, extreme circumstances.

2. Legal Reasoning

The panel’s reasoning unfolded in stages:

Existence of a Breach: The plea agreement stipulated a base offense level of 10 under U.S.S.G. § 2A2.4 (impeding officers), a two-point bodily-injury enhancement, and a total offense level of 13 (yielding an 18–24 month range for CHC III). Yet at the sentencing hearing, the prosecutor pressed for a four-level “serious bodily injury” enhancement under § 2A2.2 (aggravated assault)—a guideline never agreed to—and described the crime with words like “extraordinary,” “heinous,” and “vicious.” Those arguments necessarily required use of § 2A2.2 and triggered supplemental enhancements (e.g., “Official Victim”) that the agreement excluded.
Plain-Error Analysis: Because Maldonado had not objected to the plea-breach arguments as they unfolded, the court applied the four-prong plain-error test:
1. An error occurred (breach of plea terms);
2. The error was clear or obvious under settled law;
3. The breach affected Maldonado’s substantial rights by altering his sentencing exposure;
4. The fairness and integrity of the process were seriously impaired.
All prongs were satisfied.
Remedy: The court declined to exercise its “extraordinary” equitable power to dictate a specific time-served sentence (as in Kurkculer), because Maldonado had significant remaining exposure and a remand could still afford him full benefit of the 18–24 month agreement. Instead, the court vacated the sentence and remanded for expedited resentencing before a different district judge, with instructions that the government make good-faith recommendations in accordance with the plea agreement.

3. Impact

United States v. Maldonado-Maldonado reinforces critical principles governing plea negotiations:

Prosecutors must strictly adhere to plea-agreement terms; indirect advocacy for higher enhancements based on unrelated guidelines is a breach.
Courts will employ plain-error review if a defendant fails to object at sentencing, but a clear breach will still require vacatur.
Remand to a different judge for resentencing is the standard remedy for breach, preserving future benefits from the agreed ranges.

This decision will guide both prosecutors and defense counsel in plea negotiations and sentencing practice, underscoring that the parties’ stipulations on guidelines and ranges are sacrosanct.

Complex Concepts Simplified

Plea Agreement: A binding contract between defendant and government specifying charges, factual stipulations, guideline calculations, and recommended sentencing ranges.
Sentencing Guidelines: A grid of offense levels (Base Offense Level plus enhancements/reductions) and criminal history categories that produce advisory sentencing ranges.
Plain-Error Review: An appellate standard when a party fails to object in the trial court. The party must show clear error that affected substantial rights and the integrity of proceedings.
Specific Performance: Equitable enforcement of a plea agreement’s terms, normally binding the prosecutor but not dictating the district court’s independent sentencing decision.
Equitable Remedy: In rare cases, the appellate court may direct a specific sentence if the defendant has lost all chance to benefit from the agreement.

Conclusion

United States v. Maldonado-Maldonado confirms that prosecutors must fulfill every promise in a plea deal—not just in form but in spirit. Advocating for enhancements and guidelines excluded by the agreement is a clear breach, triggering vacatur under plain-error review. The First Circuit’s remedy—vacating the sentence and remanding for resentencing before a different judge—strikes a balance between enforcing plea agreements and preserving the district court’s sentencing discretion. This decision will resonate through plea-bargaining practice, ensuring that negotiated guideline calculations and recommended ranges are honored in both letter and essence.