Ambiguous Sentencing Rationale Requires Limited Remand for Clarification of “Association with Convicted Felons”

1. Introduction

Kevin Jadiel Figueroa-Roman participated in multiple carjackings in April 2019 alongside three associates (later codefendants), with the goal of selling the stolen vehicles. He pleaded guilty to four counts of aiding and abetting violations of 18 U.S.C. § 2119 and 18 U.S.C. § 2. At sentencing, probation calculated a Guidelines range of 70–87 months; the defense sought a below-range sentence (the hearing reflected 63 months), and the government recommended roughly the low end (70.5 months). The district court varied upward and imposed 108 months on each count, concurrently.

On appeal, Figueroa-Roman challenged the sentence as procedurally unreasonable, arguing that the district court (i) inadequately explained its rationale and (ii) relied on improper or unsupported considerations. The First Circuit did not reach the merits of those procedural-reasonableness claims. Instead, it focused on a specific sentencing remark—Figueroa-Roman’s “association with convicted felons”—and held that the ambiguity in that remark prevented meaningful appellate review.

2. Summary of the Opinion

The First Circuit vacated and remanded for clarification because it could not determine what the district court meant by stating it had balanced, among other things, Figueroa-Roman’s “association with convicted felons when assessing [his] risk to the community once he is released.” The remark was susceptible to multiple interpretations (who the “convicted felons” were, when they were “convicted,” and how any “association” factored into sentencing), and that uncertainty obstructed appellate review of whether the sentence was procedurally sound. The panel retained jurisdiction and expressly stated it did not decide whether the sentencing explanation was otherwise adequate or whether any other appellate claim had merit.

3. Analysis

3.1. Precedents Cited

The Opinion’s remand-for-clarification approach is built from a line of First Circuit cases addressing appellate review of sentencing explanations and the handling of ambiguous or potentially erroneous sentencing rationales.

• United States v. Rivera-Santiago and United States v. O'Brien
  The court cited these cases for the record sources typically used on appeal following a guilty plea—“the plea agreement, the change-of-plea colloquy, the undisputed portions of the presentence investigation report (‘PSR’), and the transcript of the disposition hearing.” This framing underscores that sentencing review is constrained by the sentencing record; where that record is unclear, appellate courts cannot reliably reconstruct the sentencing rationale.
• United States v. Colón-Cordero
  Quoted for the principle that appellate courts cannot assess sentencing validity when they do not know “to what degree the court relied” on an erroneous or uncertain fact. In Figueroa-Roman, the problem was not an identified erroneous fact but an unclear statement that could be factual, inferential, or something else. Colón-Cordero provided the template: uncertainty about reliance and degree of reliance can itself be review-precluding.
• United States v. Navarro-Santisteban
  Cited for remanding where the appellate court could not “extricate the influence” of an improper consideration from the broader sentencing rationale. Figueroa-Roman uses the same logic: without knowing what “association with convicted felons” meant, the panel could not separate any permissible reasoning from any potentially impermissible reasoning.
• United States v. Serrano-Berríos and United States v. Cáceres-Cabrera
  These cases support remand when a sentencing transcript is “open to multiple interpretations” or “can be read to support either side’s argument.” The Opinion treats ambiguity itself as the operative defect: where plausible competing readings exist and the record does not “clearly tether” the statement to known facts, clarification is required.
• United States v. Carrión-Meléndez
  Cited for the broader observation that appellate review is “frustrated when the reasons underpinning a ruling are unclear.” Importantly, Carrión-Meléndez is also used to justify a prudent, limited remand—giving the district court an opportunity to clarify and, if appropriate, reconsider the precise basis for its rationale.
• United States v. Gilman (with United States v. Feliz and United States v. McDowell in the parenthetical line)
  Gilman supplies the doctrinal mechanism: when the appellate court cannot discern the district court’s reasoning, it may vacate (even without reversing on the merits) to allow explanation at resentencing. Gilman also discusses plain-error posture: even if a shortfall is “obvious error,” an appellant still must show prejudice; conversely, where ambiguity creates a meaningful possibility of prejudice, remand may be warranted to determine what the sentencing court actually did.
• United States v. Levy
  Quoted for the practice point: “[w]here ... the record admits of possible ambiguity, our practice is to remand for a limited purpose.” Figueroa-Roman operationalizes Levy by ordering clarification while retaining appellate jurisdiction.

3.2. Legal Reasoning

The court’s reasoning proceeds in three linked steps:

1. Identify a materially ambiguous sentencing premise.
   The district court’s balancing statement included “association with convicted felons,” but the record did not reveal:
   • Who the “convicted felons” were (codefendants? other individuals?).
   • When they were “convicted” (before the offense? by the time of sentencing? after release?).
   • What “association” meant and why it mattered in a first-offender posture (especially absent any condition restricting association).
2. Connect ambiguity to the inability to conduct procedural-reasonableness review.
   Procedural reasonableness requires reviewing whether the court relied on proper facts and provided an adequate explanation. The First Circuit emphasized that it could not even choose the proper “lens of review” (including whether a factual finding was being made and what standard should apply) because it could not tell what the district court was asserting. Nor could it measure whether the remark played a meaningful role in the upward variance.
3. Select a tailored remedy: vacatur and remand for clarification, with jurisdiction retained.
   Rather than decide the procedural challenge on an incomplete understanding, the court vacated and remanded so the district court could clarify what it meant. The panel stressed it was not deciding the adequacy of the full sentencing explanation or other issues; it sought only to remove the interpretive “quandary” blocking review.

Notably, the government argued the phrase might simply refer to the fact that Figueroa-Roman and childhood friends engaged in a felony crime spree that resulted in felony convictions. The panel did not reject that reading outright; it held only that the transcript did not permit the appellate court to adopt it confidently. That restraint reflects the appellate principle that reviewing courts should not supply post hoc rationalizations where the sentencing record is genuinely susceptible to competing meanings.

3.3. Impact

• Sharper expectations for clarity in upward-variance explanations.
  Even where other aggravating factors exist (violence, psychological harm, victim statements), a single ambiguous sentencing premise can require vacatur if it might have contributed to the variance and cannot be “extricated” from the rationale.
• “Association” as a sentencing consideration must be anchored to identifiable facts.
  The Opinion signals that “association with convicted felons” is not self-defining. If it is meant as a factual finding (e.g., prior association with known felons, gang affiliation, or post-release risk markers), it must be specific enough to permit review and to avoid the appearance of relying on unproven assumptions.
• Procedural remedy: limited remand with retained jurisdiction.
  The court’s approach—vacate, remand for clarification, retain jurisdiction—provides a procedural model for efficiently curing ambiguity without forcing a full second appeal cycle on issues that may dissolve once the sentencing judge clarifies the record.
• Plain-error posture does not eliminate the need for clarity.
  The court indicated that even under plain-error review, ambiguity may matter because prejudice analysis depends on what the sentencing court actually meant and relied upon. Clarification can be a prerequisite to applying plain-error doctrine coherently.

4. Complex Concepts Simplified

• Procedural unreasonableness (sentencing).
  A sentence can be procedurally flawed if the judge used incorrect facts, relied on improper factors, failed to calculate or explain the Guidelines range correctly, or failed to adequately explain the sentence under the statutory factors.
• Guidelines range and “variance.”
  The Sentencing Guidelines provide a recommended range (here, 70–87 months). A variance occurs when the judge imposes a sentence outside that range based on statutory sentencing factors. An upward variance means above the range (here, 108 months).
• Meaningful appellate review.
  Appeals courts do not resentence defendants; they review the process and reasoning used. If the sentencing record is unclear, appellate courts cannot determine whether the process was lawful, which forces a remand to clarify.
• Plain error.
  When an issue was not properly preserved in the district court, the appellant often must show (among other things) an obvious error and a reasonable probability that it affected the outcome (prejudice). If the record is ambiguous about what the judge relied on, it may be impossible to assess prejudice without clarification.
• Vacate and remand for clarification (retained jurisdiction).
  “Vacate” nullifies the sentence. “Remand for clarification” sends the case back so the judge can explain what was meant. “Panel retains jurisdiction” means the same appellate panel keeps control of the appeal and can resume review after the clarification.

5. Conclusion

United States v. Figueroa-Roman establishes (and reinforces within First Circuit practice) a clear procedural lesson: when a sentencing judge’s stated rationale includes a material but ambiguous consideration—here, “association with convicted felons”—and the ambiguity prevents the appellate court from determining what fact (if any) was found and how it affected the sentence, the proper course is to vacate and remand for clarification. The Opinion does not decide whether the upward variance was justified; it holds that the appellate court cannot responsibly evaluate procedural reasonableness until the sentencing court’s meaning is made clear on the record. In practical terms, the decision promotes disciplined sentencing explanations and ensures that review of variances rests on ascertainable facts and transparent reasoning, not inference or guesswork.