In the United States Court of Appeals For the Seventh Circuit ____________________ No. 20-1034 UNITED STATES OF AMERICA, Plaintiff-Appellee, v. NATHANIEL RUTH, Defendant-Appellant. ____________________ Appeal from the United States District Court for the Central District of Illinois. No. 19-cr-20005 — Michael M. Mihm, Judge. ____________________ ARGUED JUNE 3, 2020 — DECIDED JULY 20, 2020 ____________________ Before SYKES, Chief Judge, and BAUER and ST. EVE, Circuit Judges. ST. EVE, Circuit Judge. In what is becoming an all-too-famil- iar subject, this appeal raises a question about whether a state drug statute sweeps more broadly than its federal counterpart because the former includes a particular isomer of a substance that the latter does not. Nathaniel Ruth pleaded guilty to fed- eral gun and drug charges and received an enhanced sentence due to his prior Illinois conviction for possession with intent 2 No. 20-1034 to deliver cocaine. The Illinois statute defines cocaine to in- clude its positional isomers, whereas the federal definition co- vers only cocaine’s optical and geometric isomers. Ruth now appeals and claims that the district court erred in sentencing him because, using the categorical approach, the overbreadth of the Illinois statute disqualifies his prior conviction as a predicate felony drug offense. We agree and therefore vacate Ruth’s sentence and remand for resentencing. I. Background We can be brief in our summary of the facts because this appeal raises challenges only to the application of sentencing enhancements, which present pure questions of law. In 2018, the Champaign, Illinois police department’s Street Crime Task Force used a confidential source to conduct multiple controlled buys of drugs from Nathaniel Ruth. That investi- gation came to a head on December 5, 2018, when officers sur- veilling Ruth pulled him over while driving and arrested Ruth for driving with a revoked license. During the arrest, Ruth told the officers that there was a firearm in the vehicle. Officers subsequently executed a search warrant at Ruth’s res- idence and recovered 2.9 grams of crack cocaine, 5.6 grams of powder cocaine, a counterfeit $100 bill, $2,250 in U.S. cur- rency, and various drug paraphernalia. A grand jury indicted Ruth on two counts: one count of possession of a firearm by a felon in violation of 18 U.S.C. § 922(g)(1), and one count of possession of cocaine with intent to distribute in violation of 21 U.S.C. § 841(a)(1), (b)(1)(C). The government then filed an information pursuant to 21 U.S.C. § 851 notifying Ruth that it intended to rely on a prior convic- tion as a predicate felony drug offense to enhance his sen- tence. Namely, the government intended to use a 2006 Illinois No. 20-1034 3 conviction for possession of a controlled substance with intent to distribute, 720 ILCS 570/401(c)(2). The § 851 enhancement increased the statutory maximum sentence from twenty years in prison to thirty years. See 21 U.S.C. § 841(b)(1)(C). Ruth did not object to the government’s § 851 notice. After ironing out a defect in the indictment, Ruth eventu- ally pleaded guilty to both counts without ...
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