United States Court of Appeals For the Seventh Circuit ____________________ No. 19-3363 CHRISTOPHER HARRIS, Petitioner-Appellant, v. UNITED STATES OF AMERICA, Respondent-Appellee. ____________________

Appeal from the United States District Court for the Southern District of Indiana, Indianapolis Division. No. 1:18-cv-03105-JMS-DML — Jane Magnus-Stinson, Judge. ____________________

ARGUED JUNE 3, 2021 — DECIDED SEPTEMBER 10, 2021 ____________________

Before MANION, WOOD, and BRENNAN, Circuit Judges. BRENNAN, Circuit Judge. Christopher Harris faced federal drug charges. Counsel advised him that his two prior Indiana cocaine convictions were predicate “felony drug offenses” and could result in a mandatory life sentence. So, Harris en- tered into a plea agreement and received an agreed-upon 20- year sentence. 2 No. 19-3363

Harris now seeks federal habeas corpus relief under 28 U.S.C. § 2255. He argues his counsel was ineffective by not challenging whether those prior drug convictions were pred- icates, as Indiana law defined cocaine isomers more broadly than federal law. Such an argument, novel then, would suc- ceed today. Although Harris forfeited this theory of ineffectiveness in the district court, we conclude that it is subject to plain-error review. But because it was objectively reasonable for Harris’s counsel not to advise risking a mandatory life sentence to pur- sue the isomer argument, the district court did not plainly err in ruling that counsel’s performance was constitutionally ad- equate. I Harris was charged in 2016 with possessing with intent to distribute 50 grams or more of methamphetamine. See 21 U.S.C. § 841(a)(1) (2010). Because of his prior drug con- victions, Harris faced significant sentencing exposure. At the time, the statutory minimum sentence for this crime was 10 years. Id. § 841(b)(1)(A)(viii) (2010). But under that statute, the government could enhance the potential sentence by arguing that two of Harris’s prior convictions were felony drug of- fenses: an Indiana conviction in 2006 for dealing cocaine, see IND. CODE § 35-48-4-1(a) (2006), and an Indiana conviction in 2001 for possessing cocaine, see id. § 35-48-4-6(a) (2001). At that time, one prior “felony drug offense” increased the man- datory minimum sentence to 20 years, while two required a life sentence. See 21 U.S.C. § 841(b)(1)(A)(viii) (2010). To avoid a life sentence, Harris reached an agreement un- der Federal Rule of Criminal Procedure 11(c)(1)(C) with the No. 19-3363 3 government to plead guilty and accept a sentence of 20 years’ imprisonment. Pursuant to that deal, the government filed a notice under 21 U.S.C. § 851 listing only one predicate offense, the 2006 Indiana conviction for dealing cocaine. At a joint change-of-plea and sentencing hearing in October 2017, the district court confirmed that “the basis” for Harris’s plea was his (and his counsel’s) understanding that he was avoiding a mandatory life sentence due to the government’s agreement not to introduce his 2001 Indiana cocaine possession convic- tion. The court also confirmed that Harris knew he was waiv- ing his right to challenge his conviction and sentence, except as to ineffective assistance of counsel. Harris did not appeal. Instead, acting pro se, he timely moved to vacate his sentence pursuant to § 2255. Harris as- serted his counsel had been ineffective “during plea bargain- ing for the failure to challenge the § 851 enhancement towards the prior dealing in cocaine case.” In his petition, Harris at- tempted to explain: Thomas Brodnick represented me during plea nego