55 F.4th 153
2d Cir.2022Background
- Defendant Vincent Gibson pled guilty to multiple 2017 federal bank-robbery offenses and was sentenced in 2020. The government sought a career-offender enhancement under U.S.S.G. § 4B1.1, which requires two prior qualifying felony convictions.
- Government relied on two prior state felonies as predicates: a 2002 New York conviction for attempted criminal sale of a controlled substance (N.Y. Penal Law §§ 220.39(1), 110) and a 2004 attempted first-degree robbery conviction.
- The 2002 NY statute defined the relevant narcotic to include substances listed in NY Schedule II(b)(1), which then included naloxegol; naloxegol was removed from the federal Controlled Substances Act (CSA) schedules in 2015.
- The district court applied the categorical approach and concluded the NY statute was broader than the federal CSA schedules in effect at sentencing (because naloxegol was no longer federally controlled), so the 2002 conviction did not qualify as a federal "controlled substance offense" for § 4B1.1 purposes; Gibson was not a career offender and received a 60‑month sentence.
- The government appealed, arguing the court should compare the NY schedule to the CSA as it existed at the time of the 2002 state conviction (not the time of federal sentencing).
- The Second Circuit affirmed, holding that federal law was narrower than the NY law both at the time of the 2002 conviction and at sentencing; it rejected the government’s reliance on McNeill and Doe as inapposite and endorsed the district court’s categorical comparison to federal schedules used by the Guidelines.
Issues
| Issue | Plaintiff's Argument | Defendant's Argument | Held |
|---|---|---|---|
| Whether a prior state controlled-substance conviction counts as a § 4B1.1 predicate when the state schedule criminalizes a substance (naloxegol) removed from the federal CSA: which version of the CSA schedules governs—the version at the time of the prior conviction or at the time of sentencing? | Compare NY law to the CSA as of the time of the 2002 state conviction; naloxegol was then federally controlled, so the conviction qualifies as a predicate. | Compare NY law to the federal schedules in effect at sentencing (or at least to the schedules applicable to federal sentencing); naloxegol was delisted in 2015, so the NY statute is broader and the conviction does not qualify. | Affirmed district court: federal schedules were narrower than NY law both at time of the 2002 conviction and at sentencing; 2002 conviction is not a § 4B1.1 predicate. The court rejected the government’s McNeill/Doe-based timing argument and applied the categorical approach referencing CSA schedules used by the Guidelines. |
Key Cases Cited
- McNeill v. United States, 563 U.S. 816 (Supreme Court 2011) (ACCA sentencing enhancement requires consulting the law in effect at the time of the prior state conviction for determining statutory maximum applicable to that conviction)
- United States v. Townsend, 897 F.3d 66 (2d Cir. 2018) (term "controlled substance" in § 4B1.2(b) refers to substances in the CSA)
- Doe v. Sessions, 886 F.3d 203 (2d Cir. 2018) (for immigration consequences, categorical analysis looks to CSA schedules in effect at time of conviction)
- Moncrieffe v. Holder, 569 U.S. 184 (Supreme Court 2013) (explains the categorical approach and presumption of conviction resting on the least conduct criminalized)
- Johnson v. United States, 559 U.S. 133 (Supreme Court 2010) (describes the categorical approach to prior convictions)
- Gall v. United States, 552 U.S. 38 (Supreme Court 2007) (district courts must calculate Guidelines range as first step in sentencing)