78 F.4th 272
6th Cir.2023Background
- Wilkes pleaded guilty to being a felon in possession of a firearm; the PSR recommended a 15‑year mandatory minimum under the ACCA based on four prior Michigan cocaine convictions (1995, 2006, 2007).
- Wilkes objected that his Michigan convictions were not ACCA ‘‘serious drug offenses’’ because Michigan law (1) included ioflupane (removed from federal schedule in 2015) and (2) used the term “stereoisomers,” which he argued covers more cocaine isomers than the federal CSA’s ‘‘optical and geometric isomers.’'
- At sentencing both sides presented chemistry experts; the district court credited the government’s expert, found the federal terms ‘‘optical and geometric isomers’’ cover the same stereoisomers Michigan bans, overruled Wilkes’s ACCA objection, and imposed 180 months’ imprisonment.
- Wilkes also objected to proffer‑protected information appearing in the PSR; the district court adopted the probation officer’s approach that the material was labeled proffer‑protected and would not affect guideline scoring, and overruled the objection.
- On appeal the Sixth Circuit affirmed the isomer ruling and the PSR ruling, but held in abeyance and retained jurisdiction over Wilkes’s separate challenge concerning ioflupane pending Supreme Court resolution of a related question in Jackson v. United States.
Issues
| Issue | Wilkes’ Argument | Government’s Argument | Held |
|---|---|---|---|
| Whether Michigan’s term “stereoisomers” sweeps more broadly than the federal CSA’s “optical and geometric isomers” for cocaine | Michigan’s “stereoisomers” covers all eight stereoisomers and thus exceeds the federal schedule because “geometric isomer” does not clearly include diastereomers | Federal “optical and geometric isomers” (as understood in 1984) encompasses cocaine’s enantiomers and diastereomers, making the statutes coextensive | Held: Federal terms include the same stereoisomers; Michigan does not sweep more broadly — ACCA predicate stands |
| Whether the ACCA comparison should look to the federal schedule at time of state conviction, the federal offense, or federal sentencing (ioflupane removal issue) | Wilkes argued federal timing might exclude ioflupane and thus invalidate the ACCA predicate | Government relied on controlling time‑of‑conviction precedent (per Clark) and argued no mismatch | Held: Decision on iofupane/timing held in abeyance pending Supreme Court resolution; Sixth Circuit retained jurisdiction |
| Whether inclusion of proffer‑protected statements in the PSR violated protections and affected sentence | Wilkes argued proffered material should not appear or be used and may affect BOP classification | Government/probation: material was labeled proffer‑protected, would not affect guideline calculations, and was properly retained for completeness | Held: Overruled below; any error was harmless because material did not affect sentencing and Wilkes failed to show plain error on new arguments |
Key Cases Cited
- Taylor v. United States, 495 U.S. 575 (establishes categorical approach for predicate offenses)
- Shular v. United States, 140 S. Ct. 779 (applies categorical approach to ACCA serious‑drug‑offense determinations)
- Descamps v. United States, 570 U.S. 254 (limits consideration to statutory elements; use of modified categorical approach when statute is divisible)
- Mathis v. United States, 579 U.S. 500 (on divisible statutes and the modified categorical approach)
- United States v. House, 872 F.3d 748 (6th Cir.) (held Mich. § 333.7401 divisible and applied modified categorical approach)
- United States v. Mateen, 764 F.3d 627 (6th Cir.) (de novo review of statutory construction for career‑offender/ACCA determinations)
- United States v. Clark, 46 F.4th 404 (6th Cir.) (adopted time‑of‑conviction rule for career‑offender analysis under the Guidelines)
- United States v. Ross, 719 F.2d 615 (discusses historical “isomer defense” to cocaine prosecutions)
- Bostock v. Clayton County, 140 S. Ct. 1731 (textualist principles; ordinary public meaning at time of enactment)
- Kisor v. Wilkie, 139 S. Ct. 2400 (agency interpretations as evidence of original public meaning)
- Puckett v. United States, 556 U.S. 129 (plain‑error framework)
- United States v. Jackson, 635 F.3d 205 (6th Cir.) (inclusion of proffer‑protected material in PSR not plain error where not used to enhance sentence)