United States v. Theodore Lee Duggan, 21-12152

In 2010 Duggan pled guilty to bank robbery and was sentenced to 120 months imprisonment followed by 36 months supervised release.
Duggan’s supervised release began in July 2020; in Oct–Nov 2020 he admitted violations (including multiple positive cocaine tests and failure to pay restitution) and the court revoked release, sentencing him to 60 days imprisonment followed by 24 months supervised release.
He began supervised release again in Jan 2021; in Mar–Apr 2021 he admitted new violations (additional positive drug/alcohol tests, continued failure to pay restitution, and failure to work). The guidelines range for revocation was 8–14 months.
At the second revocation hearing the probation officer recommended 12 months imprisonment with no supervised release; the government asked for 8 months no supervised release; Duggan asked for leniency and furlough. The court imposed 12 months + 1 day imprisonment followed by 24 months supervised release.
Duggan appealed, arguing the 24‑month supervised release term exceeded the statutory maximum after accounting for aggregate imprisonment on revocations, and that the imprisonment term was substantively unreasonable.
The Eleventh Circuit vacated the supervised release term as plain statutory error and remanded for resentencing as to supervised release, but affirmed the 12‑month + 1 day imprisonment as substantively reasonable.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether imposition of 24 months supervised release was plain error because it exceeded the statutory maximum under 18 U.S.C. § 3583(h) after accounting for prior revocation imprisonment	Duggan: 24 months exceeded the statutory cap once prior revocation imprisonment is aggregated	Government: conceded plain error	Court: Plain error; vacated supervised release term and remanded to impose no more than statutory maximum (36 months minus aggregate revocation imprisonment)
Whether the 12 months + 1 day imprisonment was substantively unreasonable under 18 U.S.C. § 3553(a)	Duggan: sentence unreasonable given his drug addiction and inadequate pandemic-era treatment opportunities	Government: sentence reasonable given Duggan’s criminal history, repeated violations, and need for deterrence/public protection	Court: Sentence of imprisonment is substantively reasonable and affirmed

United States v. Olano, 507 U.S. 725 (1993) (plain‑error framework requiring error, plainness, prejudice, and effect on fairness/integrity)
Rosales‑Mireles v. United States, 138 S. Ct. 1897 (2018) (discussing how plain errors affecting liberty and calculation undermine fairness/integrity)
United States v. Mazarky, 499 F.3d 1246 (11th Cir. 2007) (under § 3583(h) multiple revocations require reducing statutory supervised‑release maximum by aggregate imprisonment)
United States v. Gresham, 325 F.3d 1262 (11th Cir. 2003) (to show prejudice the imposed supervised release must exceed statutory permissible term)
Holguin‑Hernandez v. United States, 140 S. Ct. 762 (2020) (preserving claim that a longer sentence is substantively unreasonable by requesting a particular sentence)
United States v. Trailer, 827 F.3d 933 (11th Cir. 2016) (substantive‑reasonableness review considers the totality of circumstances and § 3553(a) factors)
United States v. Gonzalez, 550 F.3d 1319 (11th Cir. 2008) (a sentence below the statutory maximum is evidence of reasonableness)