Christopher Harris v. United States, 13 F.4th 623

In 2016 Harris was charged federally with possession with intent to distribute 50+ grams of methamphetamine; two prior Indiana cocaine convictions (2001 possession; 2006 dealing) exposed him to enhanced mandatory minimums, including life if both counted.
To avoid a life sentence he accepted a Rule 11(c)(1)(C) plea agreement for a 20-year sentence; the government filed a § 851 notice listing only the 2006 conviction.
Harris later filed a pro se § 2255 motion claiming ineffective assistance of counsel (IAC) for failing to challenge the predicate status of his prior Indiana convictions; he cited Descamps in a reply as a basis for a categorical challenge.
The district court denied relief, concluding a Descamps-style categorical challenge would have failed because the 2006 conviction fit the federal definition of a felony drug offense at the time.
After the district court decision this court decided De La Torre and Ruth, which held that some state definitions of "isomer" (and therefore of cocaine) are broader than the federal definition, potentially meaning Indiana convictions might not qualify as federal predicate felony drug offenses.
The Seventh Circuit granted a certificate of appealability, reviewed the forfeiture/preservation issue under plain-error standards, and affirmed denial of § 2255 relief, concluding counsel’s decision to accept the plea was objectively reasonable given the novel isomer theory and the risk of a mandatory life sentence.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Preservation/forfeiture of the Descamps/isomer claim	Harris: pro se reply citing Descamps reasonably raised the categorical/isomer challenge; forfeiture, not waiver, so appellate review appropriate	Government: Harris failed to present the theory in district court and thus cannot raise it on appeal	Court: Construed liberally as forfeiture (not waiver); exceptional circumstances and subsequent controlling precedents justify plain-error review
Whether counsel was constitutionally ineffective for not making a categorical challenge that Indiana's isomer definition is broader than federal law	Harris: counsel should have challenged the prior convictions as non-predicate under Descamps; if successful, would have avoided the long sentence	Government: The challenge was novel and uncertain; counsel reasonably secured a guaranteed 20-year plea rather than risk a life sentence and possible withdrawal of the plea	Court: No IAC—objective Strickland reasonableness favors accepting the plea given the novelty of the isomer argument and the severe downside risk of pressing it
Need for evidentiary hearing about counsel's subjective awareness of the isomer argument	Harris: counsel should at least have consulted him about raising the novel challenge	Government: No hearing necessary; objective reasonableness controls and record adequate	Court: No remand; subjective state not central—objective analysis dispositive; no plain error in denying § 2255

Strickland v. Washington, 466 U.S. 668 (1984) (two-pronged standard for ineffective assistance of counsel)
Descamps v. United States, 570 U.S. 254 (2013) (categorical approach requires state predicate to match federal definition)
United States v. De La Torre, 940 F.3d 938 (7th Cir. 2019) (Indiana isomer definition broader than federal law)
United States v. Ruth, 966 F.3d 642 (7th Cir. 2020) (state cocaine definition including isomers broader than federal definition)
Puckett v. United States, 556 U.S. 129 (2009) (plain-error review framework)
Bourgeois v. Watson, 977 F.3d 620 (7th Cir. 2020) (criteria for addressing forfeited issues in collateral context)
Custis v. United States, 511 U.S. 485 (1994) (limits on collateral attacks of prior state convictions at federal sentencing)
Bridges v. United States, 991 F.3d 793 (7th Cir. 2021) (defense counsel may need to anticipate nascent legal arguments; objective reasonableness analysis)
Gaylord v. United States, 829 F.3d 500 (7th Cir. 2016) (counsel must advise defendant of likely sentence and relevant established challenges before plea)
Taylor v. United States, 495 U.S. 575 (1990) (foundational decision adopting the categorical approach)
Missouri v. Frye, 566 U.S. 134 (2012) (prejudice in plea context where reasonable probability of a lesser sentence exists)
Harrington v. Richter, 562 U.S. 86 (2011) (deference to counsel’s objectively reasonable strategic decisions)