“Unmistakable Clarity” Required: United States v. Maldonado-Negroni and the Harmless-Error Test for Guideline Miscalculations

1. Introduction

United States v. Maldonado-Negroni, No. 23-1768 (1st Cir. 2025), arises from a third revocation of supervised release imposed after Xavier O. Maldonado-Negroni’s 2013 federal drug-trafficking conviction. The appeal presented a narrow yet recurring question: When the sentencing court misclassifies the grade of a supervised-release violation and thus applies the wrong Sentencing Guideline range, what showing is necessary for the government to prove that the error was harmless?

The district court treated Maldonado’s Puerto Rico domestic-violence offense as a Grade A violation (12–18 months), rather than the correct Grade B violation (4–10 months), and imposed the statutory maximum of 36 months. When the government, after the sentence had been pronounced, asked whether the court would have imposed the same sentence under either grade, the court responded with a single word—“Yes.” On appeal, the First Circuit held that this perfunctory assurance failed to satisfy the government’s burden to show that the miscalculation was harmless.

2. Summary of the Judgment

Error Identified: The district court erroneously classified the Puerto Rico Domestic Abuse Prevention and Intervention Act violations (Arts. 3.2 & 3.3) as “crimes of violence,” thereby applying Grade A instead of Grade B.
Holding: A district court’s brief, post-pronouncement statement that it would impose the same sentence “regardless of the guideline” is insufficient to render a Guidelines error harmless. The sentence was vacated and the case remanded for resentencing.
Standard Articulated: When the wrong Guideline range has been used, the record must make the absence of prejudice “unmistakable.” Conclusory statements lacking explanation do not meet this standard.

3. Detailed Analysis

3.1 Precedents Cited

Molina-Martinez v. United States, 578 U.S. 189 (2016) – Burden on government to prove harmlessness when Guideline error preserved.
United States v. Ouellette, 985 F.3d 107 (1st Cir. 2021) & United States v. Ahmed, 51 F.4th 12 (1st Cir. 2022) – Examples where explicit “untethered from the Guidelines” language satisfied harmless-error review.
United States v. Taylor, 848 F.3d 476 (1st Cir. 2017) – A terse post-sentence “yes” did not render an error harmless.
United States v. Menéndez-Montalvo, 88 F.4th 326 (1st Cir. 2023) – Held Article 3.1 of the Puerto Rico domestic-violence statute not a crime of violence; reasoning extended to Articles 3.2 & 3.3 here.
Additional anchors: Romero-Galíndez, Hudson, Tavares, and Supreme Court decisions Gall and Peugh on the anchoring role of the Guidelines.

3.2 Court’s Legal Reasoning

The First Circuit’s reasoning unfolds in three steps:

Existence of Error. The government conceded—after the intervening Menéndez-Montalvo decision—that the district court’s “crime-of-violence” determination was wrong, making the operative range 4–10 months.
Harmless-Error Framework. Under Molina-Martinez, once an error is preserved, the government must prove harmlessness. Sentencing errors are harmless only if the record makes their “innocuous nature unmistakable.”
Application to the Facts. The district court’s single “Yes”:
- was delivered after sentencing, in response to a government prompt;
- contained no explanation or indication that the court weighed the larger variance required under Grade B (3.6× the top of the range) versus Grade A (2×);
- contrasted sharply with prior cases where judges explicitly stated their sentence was “untethered” from the Guidelines.

Because the record was ambiguous—and because the Guidelines’ “anchoring effect” is presumed—the First Circuit could not be certain that the incorrect range played no role. Accordingly, it vacated the sentence.

3.3 Impact of the Decision

Higher Bar for Harmlessness. District courts in the First Circuit must now provide clear, on-the-record explanations if they wish to assert that they would impose the same sentence regardless of the Guideline range.
Sentencing Practice. Judges will likely incorporate more explicit language (e.g., “untethered,” “independent of the Guidelines”) and explain their reasoning to pre-empt appealable error.
Prosecutorial Strategy. The government may insist on contemporaneous clarifying statements before pronouncement rather than post-hoc questions; otherwise, the burden of proving harmlessness becomes difficult.
Defense Advocacy. Defense counsel can leverage Maldonado-Negroni to challenge sentences where the court gives only perfunctory assurances after miscalculating Guidelines.
Guideline Integrity. The case safeguards the role of the Sentencing Guidelines by preventing silent disregard, ensuring that any departure is transparent and reviewable.

4. Complex Concepts Simplified

Supervised Release: A period of community supervision after imprisonment during which the defendant must comply with specific conditions.
Guidelines “Grades” (A, B, C): Categories reflecting the seriousness of a supervised-release violation. Grade A (most serious) → longer advisory range; Grade C (least serious).
Crime of Violence: A term of art in the Guidelines triggering higher penalties; courts use a categorical approach to decide whether a statute qualifies.
Harmless Error: A legal doctrine allowing an appellate court to affirm despite error if the government proves the error did not affect the outcome.
Anchoring Effect: Psychological principle recognized in sentencing—starting numbers tend to pull outcomes toward them. Hence, mis-calculated ranges risk longer sentences.

5. Conclusion

United States v. Maldonado-Negroni fortifies the principle that sentencing errors related to the Guidelines demand rigorous scrutiny. A district court must do more than utter a perfunctory “yes” to immunize its sentence from reversal; it must articulate why the chosen sentence stands independent of any miscalculated range. The decision thus promotes transparency, preserves the centrality of the Sentencing Guidelines, and offers parties clearer guidance on the evidentiary burden required to establish harmless error. In the broader context, Maldonado-Negroni serves as a cautionary tale: where liberty is at stake, appellate courts will insist on “unmistakable clarity” before deeming any Guidelines mistake inconsequential.