United States v. Nathaniel Ruth, 966 F.3d 642

In 2018 Ruth was arrested after controlled buys and a traffic stop; agents seized powder and crack cocaine and a firearm. He pled guilty to possession of a firearm by a felon (18 U.S.C. § 922(g)(1)) and possession with intent to distribute cocaine (21 U.S.C. § 841(a)(1)).
The government filed a § 851 information seeking a statutory enhancement based on Ruth’s 2006 Illinois conviction for possession with intent to deliver cocaine under 720 ILCS 570/401(c)(2). The enhancement raised the statutory maximum from 20 to 30 years.
The Illinois definition of cocaine expressly includes optical, positional, and geometric isomers; the federal CSA lists only optical and geometric isomers—on its face, Illinois is broader.
At sentencing Ruth objected to career-offender treatment under the Guidelines (preserving that challenge) but did not object to the § 851 notice (forfeiting that argument; reviewed for plain error on appeal).
The district court applied both the § 851 enhancement and the career-offender guideline, producing an elevated Guidelines range; the court ultimately imposed concurrent 108-month terms. On appeal the Seventh Circuit vacated and remanded for resentencing because the § 851 enhancement was erroneously applied, but upheld the career-offender classification.

Issue	Plaintiff's Argument (Ruth)	Defendant's Argument (Government)	Held
Whether Ruth’s 2006 IL conviction qualifies as a predicate “felony drug offense” for § 841(b)(1)(C)/§ 851	IL statute is categorically broader (includes positional isomers) so the conviction does not necessarily involve conduct the federal statute forbids	Illinois law substantially corresponds to federal law; positional isomers are practically nonexistent; statute (or higher-level provisions) is divisible so modified categorical approach applies	The court held Illinois § 401(c)(2) is categorically broader and indivisible; § 851 enhancement was plain error and sentence vacated and remanded for resentencing
Whether Ruth’s 2006 IL conviction is a “controlled substance offense” under U.S.S.G. § 4B1.2(b) for career-offender treatment	The Guidelines should incorporate the federal CSA definition of “controlled substance”; because Illinois covers more substances, the conviction cannot serve as a predicate	The Guidelines’ definition does not cross-reference the CSA and plainly includes qualifying state-law offenses; therefore Illinois convictions can qualify	The court held the career-offender enhancement was proper: the Guidelines do not incorporate the federal CSA definition and Ruth’s IL cocaine conviction counts as a controlled substance offense

Taylor v. United States, 495 U.S. 575 (establishing the categorical/generic-offense methodology)
Shular v. United States, 140 S. Ct. 779 (holding drug-enhancement provisions use a conduct-based categorical method)
Quarles v. United States, 139 S. Ct. 1872 (discussing "substantial correspondence" in generic-offense context)
Descamps v. United States, 570 U.S. 254 (explaining divisibility and the modified categorical approach)
Shepard v. United States, 544 U.S. 13 (limiting the documents a court may consult under the modified categorical approach)
Molina-Martinez v. United States, 136 S. Ct. 1338 (Guidelines-range errors ordinarily affect substantial rights)
Olano v. United States, 507 U.S. 725 (plain-error review standard)
United States v. De La Torre, 940 F.3d 938 (7th Cir. decision recognizing isomer-based overbreadth of a state drug statute)
United States v. Hudson, 618 F.3d 700 (7th Cir. interpreting "controlled substance offense" in the Guidelines to include state-law offenses)