United States v. Orsini, 907 F.3d 115

Orsini pleaded guilty to a federal narcotics conspiracy and a PSI recommended career‑offender treatment under U.S.S.G. §4B1.1 based on three prior drug convictions (2002 MA, 2012 NH, 2013 MA).
Orsini objected to certain PSI-credited offenses as mistaken identity but did not challenge the three specified career‑offender predicate convictions.
At a pre-sentence conference the district court indicated it would classify Orsini as a career offender; defense counsel and Orsini repeatedly acknowledged and accepted career‑offender status on the record.
The parties and court agreed to stipulate a guideline range (188–235 months) based on career‑offender classification; in exchange the government abandoned efforts to pursue increased drug‑quantity, firearms, and role enhancements.
At sentencing the prosecutor admitted exhibits proving the predicate convictions, defense counsel and Orsini confirmed career‑offender status, and the court sentenced Orsini to 188 months.
On appeal new counsel argued two prior convictions did not qualify as career‑offender predicates; the government argued Orsini waived that claim by affirming career‑offender status below.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether Orsini may challenge career‑offender classification on appeal despite admitting it at sentencing	Government: Orsini waived the challenge by affirmatively accepting career‑offender status and obtaining a sentencing benefit	Orsini: His prior factual objections to the PSI preserved the right to contest predicate convictions on appeal	Waiver enforced: Orsini knowingly relinquished the claim as part of a tactical trade; no equitable basis to excuse waiver
Whether an exception to waiver should be made to consider the merits of the predicate‑conviction challenge	Government: No extraordinary circumstances; defendant got a sentencing benefit	Orsini: Waiver should be excused due to the issues' legal nature and potential merit	No exception: Court found no compelling equities, no intervening law, and that allowing reversal would unfairly prejudice the government

Descamps v. United States, 570 U.S. 254 (discusses categorical/modified categorical approach for predicate offenses)
United States v. Dávila‑Félix, 667 F.3d 47 (1st Cir.) (categorical approach discussion)
United States v. Rodriguez, 311 F.3d 435 (1st Cir. 2002) (defines waiver as intentional relinquishment)
Nat'l Ass'n of Social Workers v. Harwood, 69 F.3d 622 (1st Cir. 1995) (waiver rule and its salutary purposes)
United States v. Torres‑Rosario, 658 F.3d 110 (1st Cir.) (affirmation below ordinarily waives later challenge)
United States v. Bauzó‑Santiago, 867 F.3d 13 (1st Cir.) (party who affirms fact risks waiving rights)
United States v. Turbides‑Leonardo, 468 F.3d 34 (1st Cir.) (accepting probation department configuration waives related complaints)
United States v. Morillo, 8 F.3d 864 (1st Cir.) (similar waiver principles)
United States v. Eisom, 585 F.3d 552 (1st Cir.) (withdrawing objection below constitutes waiver)
Sindi v. El‑Moslimany, 896 F.3d 1 (1st Cir.) (factors for excusing preservation failures)