Missing a Ruth Categorical Challenge Is Not Per Se Ineffective Assistance: Stage‑Specific Limits and the “Clearly Stronger” Test in Neal v. United States (7th Cir. 2025)

Introduction

In Tyree M. Neal, Jr. v. United States, the Seventh Circuit clarified when counsel’s failure to raise a “Ruth-style” categorical challenge to a federal drug recidivism enhancement constitutes ineffective assistance of counsel under Strickland v. Washington. The court harmonizes two of its recent guideposts—Harris v. United States (2021) and Coleman v. United States (2023)—and draws sharp, stage-specific boundaries around defense counsel’s obligations to recognize and deploy categorical-approach arguments aimed at enhancements under 21 U.S.C. § 841(b).

After Neal pleaded guilty to a cocaine conspiracy, the district court applied a § 841(b)(1)(C) recidivism enhancement based on an Illinois cocaine conviction, raising his maximum sentence from 20 to 30 years. Post-sentencing, the Seventh Circuit in United States v. Ruth (2020) held that Illinois’s definition of cocaine (which includes positional isomers) is categorically broader than the federal definition (which covers only optical and geometric isomers), making Illinois cocaine convictions invalid predicates for § 841(b)(1)(C) enhancements. Neal sought relief under 28 U.S.C. § 2255, arguing that his plea, sentencing, and appellate counsel were constitutionally ineffective for not raising what later succeeded in Ruth. The district court denied relief; Neal appealed.

The Seventh Circuit affirmed. The court holds that missing a Ruth argument is not automatically deficient performance; counsel’s obligations are assessed objectively, in real time, and vary by litigation stage. For appellate counsel, an omitted issue must be both “obvious” and “clearly stronger” than the issues raised. For plea and sentencing counsel, strategic choices in a discretionary sentencing regime—especially pre-Elder and pre-Ruth—can be reasonable even if they do not anticipate a later doctrinal shift. The decision also underscores that ineffective-assistance doctrine cannot be used to make Ruth retroactive in substance.

Summary of the Judgment

The court affirms denial of Neal’s § 2255 motion.
Appellate counsel (Christiansen): Not constitutionally ineffective for omitting a Ruth-style categorical challenge. At the time of Neal’s appeal (2018), the argument was not “clearly stronger” than the plea-withdrawal issues counsel chose. The court rejects a hindsight-driven, per se rule.
Sentencing counsel (Goeke): Not deficient for not raising a Ruth challenge in 2017. Pre-Elder, the law’s trajectory was unsettled; Neal faced discretionary (not mandatory life) sentencing; counsel reasonably pursued other enhancement challenges and negotiated toward a 20-year cap.
Plea counsel (Winslow): Not deficient in 2016 for not advising about a novel categorical approach argument; raising it risked a superseding indictment exposing Neal to a life maximum. Counsel need not canvass every unsettled sentencing theory during plea talks.
Key doctrinal clarification: Coleman does not impose a per se duty on counsel at all stages to identify and raise Ruth arguments. Duties are stage- and context-sensitive, and the “clearly stronger” standard limits ineffective-assistance claims aimed at appellate issue selection.

Detailed Analysis

1) Precedents Cited and How They Shaped the Decision

Strickland v. Washington, 466 U.S. 668 (1984): Governs ineffective assistance claims—deficient performance and prejudice. The court’s analysis here turns almost entirely on the performance prong.
Makiel v. Butler, 782 F.3d 882 (7th Cir. 2015): Appellate counsel is ineffective only if an omitted issue was “obvious” and “clearly stronger” than the issues raised. This “special gloss” frames the appellate-counsel analysis and supports affirmance.
Harris v. United States, 13 F.4th 623 (7th Cir. 2021): Counsel must sometimes anticipate arguments foreshadowed by existing law. Yet in 2017, with no isomer-mismatch caselaw, taking a plea to avoid mandatory life was reasonable; declining a novel categorical challenge was not deficient. Neal relies on Harris’s principle that categorical challenges were “on the radar,” but Harris simultaneously emphasizes context and strategic options.
Coleman v. United States, 79 F.4th 822 (7th Cir. 2023): Held that by 2014, competent counsel should have at least considered a categorical challenge to an Illinois cocaine predicate where a § 851 enhancement drove a mandatory life sentence. Neal clarifies that Coleman does not create a per se rule of deficiency; life-sentence stakes, timing, and stage matter.
White v. United States, 8 F.4th 547 (7th Cir. 2021) and United States v. Vaughn, 62 F.4th 1071 (7th Cir. 2023): Ruth is not retroactive on collateral review; failing to raise Ruth earlier can be procedurally defaulted. Neal resists transforming ineffective-assistance doctrine into a backdoor form of retroactivity.
The categorical-approach line:
- Taylor v. United States, 495 U.S. 575 (1990): The foundational categorical approach.
- Brock-Miller v. United States, 887 F.3d 298 (7th Cir. 2018): In April 2018, the Seventh Circuit flagged but did not decide whether the categorical approach applies to § 841 “felony drug offense.”
- United States v. Elder, 900 F.3d 491 (7th Cir. 2018): In August 2018, the Seventh Circuit adopted the categorical approach for § 841 enhancements; an Arizona statute broader than federal law could not serve as a predicate.
- United States v. De La Torre, 940 F.3d 938 (7th Cir. 2019): Identified isomer mismatch for methamphetamine (federal law covers only optical isomers; state law broader), rendering the state statute overbroad under the categorical approach.
- United States v. Garcia, 948 F.3d 789 (7th Cir. 2020): Indiana’s inclusion of salvia (not federally scheduled) was an easy overbreadth case.
- United States v. Ruth, 966 F.3d 642 (7th Cir. 2020): Illinois’s definition of “cocaine”—including positional isomers—was categorically broader than federal law; Illinois cocaine convictions do not qualify as predicates under § 841(b)(1)(C).
Other cited guidance:
- Harrington v. Richter, 562 U.S. 86 (2011) and Yarborough v. Gentry, 540 U.S. 1 (2003): Ineffective-assistance review is highly deferential and objective, not a hindsight exercise.
- Shaw v. Wilson, 721 F.3d 908 (7th Cir. 2013) and Cates v. United States, 882 F.3d 731 (7th Cir. 2018): Examples where appellate performance fell below minimum standards (e.g., raising only a dead-on-arrival claim or omitting a flatly winning argument)—contrasted here to show why Christiansen’s choices were not constitutionally deficient.
- United States v. Page, 123 F.4th 851 (7th Cir. 2024) (en banc): Acknowledged prior “tension and inconsistency” in buyer-seller jurisprudence (relevant to the reasonableness of appellate counsel’s choice to attack the plea rather than the sentence).
- Lee v. United States, 582 U.S. 357 (2017) and Hill v. Lockhart, 474 U.S. 52 (1985): Plea-stage prejudice standards—invoked but not reached because performance was reasonable.

2) The Court’s Legal Reasoning

The Seventh Circuit’s analysis proceeds through the Strickland performance prong for each of the three attorneys, carefully situating their duties in time and in the procedural posture they occupied. The through-line is an insistence on contemporaneous, stage-sensitive evaluation rather than hindsight.

a) Appellate Counsel: The “Obvious and Clearly Stronger” Hurdle

Timing and posture: Christiansen briefed Neal’s appeal in mid-2018 and argued in October 2018. Elder, which adopted the categorical approach for § 841, was decided in August 2018; De La Torre (isomer mismatch) came in 2019; Ruth (Illinois cocaine) in 2020.
Omitted issue strength: A Ruth-style challenge was emerging but unsettled. Elder would have supported application of the categorical approach, and De La Torre later validated isomer-based overbreadth. Ruth, decided on plain error, showed that such a challenge could win even without preservation. Nonetheless, at the time of Neal’s appeal the path from Elder to Illinois cocaine was not yet settled.
Issues actually raised: Christiansen pursued plea-withdrawal challenges (involuntariness and insufficient factual basis). Although ultimately unsuccessful, these were colorable in a then-turbulent buyer-seller/conspiracy landscape.
The comparative test: The court holds the Ruth argument was not “clearly stronger” than the plea-withdrawal claims when assessed at the time. Different objectives mattered: the appellate issues targeted vacatur of the conviction (a chance at acquittal), whereas a Ruth challenge would only reduce the maximum sentence to 20 years. Appellate advocates are not required to dilute selected issues by adding every plausible alternative, especially under page limits and strategic focus concerns.
No per se rule: The court rejects reading Coleman to require that every defense attorney at every stage since 2014 must have recognized and raised the Ruth argument. The Sixth Amendment tolerates incremental legal development and strategic selectivity on appeal.

b) Sentencing Counsel: Strategy in a Discretionary Regime

Timing: Goeke represented Neal at sentencing in 2017—before Elder adopted the categorical approach for § 841 enhancements.
Context and options: Unlike Coleman’s mandatory life-stakes, Neal faced a discretionary range (and, crucially, the court could still impose 20 years even if the enhancement applied). Goeke focused on contesting other enhancements (violence, obstruction, reckless endangerment) and negotiated toward an agreement capping the recommendation at 20 years—functionally equivalent to a successful Ruth outcome if the district court followed it.
Reasonableness: Given unsettled law and viable paths to a favorable outcome, Goeke’s performance fell within the wide range of reasonable professional assistance. Harris underscores that declining to press a novel question where it would detract from a concrete sentencing strategy is not deficient.

c) Plea Counsel: Advising Amid Legal Uncertainty and Charging Risk

Timing: Winslow advised Neal in 2016, when a categorical challenge to § 841 predicates was a novel, not-yet-adopted theory in the Seventh Circuit.
Duty to consult: Counsel need not flag every potential, unsettled sentencing challenge during plea negotiations. Gaylord and Harris recognize a duty to advise on viable, established challenges; in 2016, a Ruth-style argument was not that.
Leverage and risk: Raising a categorical challenge as leverage risked provoking a superseding indictment under § 841(b)(1)(A) with a life maximum, substantially worsening Neal’s exposure. It was reasonable not to hazard that trade-off.
Result: On this record, Winslow’s performance was not objectively unreasonable, so the court did not reach prejudice (whether Neal would have gone to trial but for the advice).

d) Harmonizing Harris and Coleman; avoiding backdoor retroactivity

Harris: Recognizes counsel should sometimes anticipate foreshadowed arguments, but holds that rejecting a novel mismatch theory in favor of a plea to avoid mandatory life is reasonable.
Coleman: By 2014, a categorical approach to § 841 was sufficiently foreshadowed that, where a § 851 enhancement threatened mandatory life, failure to even consider a categorical challenge could be deficient—subject to counsel’s strategic reasons.
Neal’s synthesis: No per se deficiency from missing Ruth; stage, timing, and stakes matter. The court emphasizes that expanding Coleman to all stages and sentences would improperly make Ruth retroactive through the guise of ineffective assistance, contrary to White and Vaughn.

3) Impact and Practical Consequences

No automatic habeas relief after Ruth: Defendants whose enhancements would be invalid post-Ruth cannot obtain collateral relief simply because counsel missed the argument; they must satisfy Strickland’s performance standard as applied to their specific stage and timeframe.
Stage-sensitive duties clarified:
- Plea stage: Counsel is not obligated to advise on every unsettled legal theory; charging risks and bargaining dynamics matter.
- Sentencing stage (discretionary): Reasonable to prioritize concrete mitigation strategies over novel theories, especially pre-Elder.
- Appellate stage: Omitted issues must be not only “obvious” but also “clearly stronger” than the issues actually raised. Strategic curation is protected; “kitchen-sink” briefing is discouraged.
Coleman narrowed to its facts: The strongest duty to identify and consider a categorical challenge arises where a § 851 enhancement drives a mandatory life sentence. Outside that context, counsel’s choices receive wider deference.
Documented strategy matters: Defense lawyers should contemporaneously document their strategic assessments of categorical-approach issues, especially when stakes are high. But Neal confirms that inadvertence, without more, does not automatically equal deficiency.
Procedural default and retroactivity guardrails: White and Vaughn remain intact; Neal resists using Strickland as a backdoor to make Ruth retroactive.
Government charging leverage: The opinion candidly recognizes that pushing novel arguments during plea talks can trigger more serious charging—an important, real-world factor in assessing reasonableness.

Complex Concepts Simplified

Categorical approach: A method that compares the elements of a prior conviction with the federal definition to see if the state offense is the same as or narrower than the federal analogue. Courts do not look at the defendant’s actual facts but only at the statutes’ elements.
Isomers (optical, geometric, positional): Molecules with the same atoms arranged differently. Federal drug schedules often specify which isomers count. If a state statute covers more types of isomers than federal law, it is broader and cannot serve as a predicate under the categorical approach.
§ 841(b)(1)(C) recidivism enhancement and § 851 notice: The government may file a § 851 notice to seek a higher statutory maximum based on certain prior drug convictions. Whether a state drug conviction “counts” depends on a categorical comparison.
Plain error review: On appeal, unpreserved errors can be corrected if they are clear or obvious, affect substantial rights, and seriously affect the fairness or integrity of proceedings. Ruth itself succeeded on plain error; that does not mean counsel must always raise a novel plain-error claim.
“Clearly stronger” test (appellate ineffectiveness): An omitted issue supports an ineffective-assistance claim only if it was obvious and clearly stronger than the issues counsel did raise. This protects strategic winnowing on appeal.
Buyer-seller vs. conspiracy: A recurring distinction in drug cases. Mere repeated purchases—even on credit—can creep toward conspiracy if the facts imply a shared distribution purpose. Seventh Circuit law on this was unsettled for years, making appellate choices harder to handicap.
Procedural default and retroactivity: Claims not raised on direct review are often defaulted in collateral proceedings unless cause and prejudice are shown. New rules like Ruth are typically not retroactive on collateral review; ineffective-assistance doctrine cannot simply override that.

Case Timeline (for orientation)

2014–2015: Indictment and arrest; government files § 851 notice based on 2007 Illinois cocaine conviction.
2016: Guilty plea; plea counsel Winslow advises during negotiations.
2017: Sentencing; sentencing counsel Goeke contests several enhancements; statutory max set at 30 years; Neal receives 30 years.
2018: Direct appeal; appellate counsel Christiansen challenges plea validity; Seventh Circuit affirms. In August 2018, Elder adopts the categorical approach for § 841 enhancements.
2019: De La Torre recognizes an isomer mismatch for methamphetamine under Indiana law.
2020: Ruth holds Illinois cocaine convictions cannot support § 841(b)(1)(C) enhancements (positional isomer overbreadth).
2021–2023: Harris and Coleman set bookends on counsel’s duties regarding categorical challenges; White and Vaughn limit Ruth’s retroactivity.
2025: Seventh Circuit affirms denial of Neal’s § 2255 motion.

Conclusion

Neal v. United States is an important calibration of ineffective-assistance doctrine in the wake of Ruth. The Seventh Circuit rejects a one-size-fits-all rule that would deem counsel ineffective whenever they missed a Ruth-style categorical challenge. Instead, the court:

Harmonizes Harris and Coleman by emphasizing stage, timing, stakes, and strategy;
Reaffirms the “obvious and clearly stronger” constraint on second-guessing appellate issue selection;
Recognizes real-world charging leverage and discretionary sentencing as legitimate considerations for plea and sentencing counsel;
Guards against backdoor retroactivity of Ruth through Strickland.

For practitioners, the message is twofold. First, categorical-approach comparisons are part of competent representation, and when an enhancement drives draconian, mandatory outcomes, counsel should at least consider and document potential mismatch arguments. Second, appellate and trial strategies must be judged in their time and posture: strategic triage remains protected, and ineffective-assistance review resists hindsight. The court’s structured, stage-specific analysis in Neal will shape future § 2255 litigation across the Seventh Circuit whenever defendants claim their lawyers should have foreseen the next doctrinal turn.