Introduction

On 13 August 2025 the Seventh Circuit delivered a significant opinion in United States v. Deon Pugh, cementing two doctrinal points that have generated extensive litigation in recent years:

• Whether an inchoate drug offense (e.g., conspiracy) qualifies as a “controlled substance offense” for purposes of the federal career-offender guideline, U.S.S.G. §4B1.1.
• Whether applying the post-2017 version of §4B1.2—which now expressly includes inchoate offenses—violates the Ex Post Facto Clause when the defendant’s criminal conduct predates the Guideline change.

Defendant-appellant Deon Pugh, convicted after a bench trial of heroin trafficking and firearm charges, contested three aspects of his 216-month sentence:

1. Designation as a career offender.
2. Attribution of more than 1,000 grams of heroin in calculating his base offense level.
3. Imposition of a four-level leadership enhancement under §3B1.1(a).

The Court of Appeals (Judges Easterbrook, Jackson-Akiwumi & Pryor) affirmed on each ground, issuing a precedential opinion that clarifies the continued vitality of Stinson v. United States and its deference regime despite the Supreme Court’s 2019 decision in Kisor v. Wilkie.

Summary of the Judgment

The Seventh Circuit ruled that:

• Career-Offender Designation: Pugh was properly deemed a career offender even under the pre-2023 Guidelines because longstanding circuit precedent defers to Application Note 1 to §4B1.2, which includes conspiracies. Consequently, no Ex Post Facto violation occurred by using the 2023 text that simply codified the Note.
• Drug-Quantity Calculation: Pugh affirmatively endorsed the attribution of approximately 2,236 grams of heroin, thereby waiving any appellate challenge to that finding.
• Leadership Enhancement: The record supported a four-level increase; Pugh functioned as a joint venture leader with Mason, exercised authority over several co-conspirators, and managed wholesale supplies.

Analysis

Precedents Cited and their Influence

• Stinson v. United States, 508 U.S. 36 (1993) — Established that Sentencing Commission commentary is “authoritative unless plainly erroneous or inconsistent with the guideline.” The panel reiterated that Stinson remains controlling in the sentencing context.
• Kisor v. Wilkie, 588 U.S. 558 (2019) — Limited deference (Auer) to agency interpretations of ambiguous regulations. Pugh argued Kisor undermines Stinson. The Court rejected this, noting the Sentencing Commission’s unique role within the judiciary, not the executive.
• Peugh v. United States, 569 U.S. 530 (2013) — Provides the modern test for Ex Post Facto claims involving Sentencing Guidelines. The panel distinguished Peugh because Pugh’s guideline range was not increased relative to the pre-2017 regime once Application Note 1 is accounted for.
• United States v. Vasquez-Abarca, 946 F.3d 990 (7th Cir. 2020) — Restated the Peugh framework; cited to show that a defendant must demonstrate a higher range under the newer Guidelines.
• United States v. White, 97 F.4th 532 (7th Cir. 2024) — Precedential decision after Kisor that explicitly reaffirmed deference to Application Note 1; pivotal to today’s holding.
• Additional circuit cases (Vallone, Colon, Longstreet, Jones, etc.) informed the leadership-role analysis and waiver doctrine.

Legal Reasoning

The Court’s reasoning unfolded in three sequential steps:

1. Career-Offender Inquiry (Guideline §4B1.1)
   

   1. Was Pugh ≥18 years old?
   2. Is the instant offense a felony controlled-substance offense?
   3. Does he have ≥2 prior felony controlled-substance convictions?

   The battle centered on part 2. The panel held that—even before the 2023 text revision—circuit precedent treated an inchoate drug conspiracy as a §4B1.2 controlled-substance offense, giving “authoritative” weight to Application Note 1. Because Pugh could not show harsher treatment under the 2023 version, his Ex Post Facto argument failed at the preliminary causation step required by Peugh.
2. Drug-Quantity Calculation
   Applying United States v. Nichols, the Court distinguished waiver from forfeiture. Pugh not only failed to object but affirmatively advocated for the 2,236-gram figure. Waiver extinguishes appellate review.
3. Leadership Enhancement (§3B1.1)
   The panel reviewed de novo whether the undisputed facts supported the leadership enhancement. It upheld the finding, emphasizing:
   • Evidence of joint decision-making with Mason.
   • Direction given to Wiltz, Pearson, and Williams.
   • Oversight of wholesale procurement and repackaging operations.
   Given the deferential “matter of degree” standard, the district court’s decision to apply the four-level, rather than three-level, increase was not clearly erroneous.

Impact of the Judgment

• Stability in Sentencing Law: By reaffirming Stinson deference post-Kisor, the Seventh Circuit preserves a stable interpretive framework for the Guidelines, limiting the ripple effect of Kisor in criminal sentencing.
• Career-Offender Landscape: Defendants convicted of pre-2023 drug conspiracies within the Seventh Circuit cannot circumvent §4B1.1(a) by invoking Ex Post Facto arguments; Application Note 1 suffices to include conspiracies.
• Plea & Trial Strategy: Defense counsel must weigh carefully any strategic decision to concede drug weights or role adjustments—such concessions will likely be deemed waiver and foreclose appellate review.
• Guideline Amendments: The decision suggests that future clarifying amendments from the Sentencing Commission will rarely produce Ex Post Facto concerns so long as circuit precedent already interpreted the prior text in the same way.

Complex Concepts Simplified

• Controlled-Substance Offense: Any felony involving the manufacture, distribution, or possession with intent to distribute a controlled substance. The question here was whether conspiracy to commit such an offense counts; the Court said yes.
• Inchoate Offense: An “incomplete” crime where the illegal aim has not been fully consummated (e.g., attempt, conspiracy, solicitation).
• Career Offender (Guideline §4B1.1): A status that dramatically raises a defendant’s offense level and criminal history category if he is an adult who commits a qualifying violent or drug felony and has at least two prior qualifying felonies.
• Application Note: Commentary published by the Sentencing Commission to explain how a guideline should be applied. Under Stinson, notes are authoritative unless plainly wrong.
• Ex Post Facto Clause: Constitutional prohibition against laws that retroactively increase punishment. It applies to substantive, but not merely procedural, changes.
• Waiver vs. Forfeiture: Waiver is the intentional relinquishment of a right; forfeiture is the accidental failure to assert it. Waiver bars appellate review; forfeiture allows plain-error review.
• Leadership Enhancement (§3B1.1(a)): Adds four offense levels if the defendant was an “organizer or leader” of criminal activity involving five or more participants.
• Converted Drug Weight: A method that converts different controlled substances into a marihuana equivalent so disparate drugs can be aggregated under §2D1.1.

Conclusion

United States v. Deon Pugh fortifies the doctrinal bridge between Stinson and modern administrative-law developments, confirming that Sentencing Commission commentary retains authoritative force within the Seventh Circuit. By holding that conspiracies are controlled-substance offenses for career-offender purposes, the Court eliminates a major line of attack used by defendants whose criminal conduct pre-dated the 2023 Guideline amendment.

Beyond the marquee Ex Post Facto ruling, the decision underscores the strategic stakes of stipulating to drug quantities and role adjustments, reminding practitioners that concessions made at sentencing will likely be deemed unreviewable waivers. Finally, the Court’s measured application of §3B1.1(a) confirms that multiple leaders can coexist within a single conspiracy, provided the evidence demonstrates genuine authority and decision-making power.

Going forward, district courts within the Seventh Circuit—and arguably in other circuits looking for persuasive authority—can rely on Pugh to:

• Apply the career-offender enhancement to drug-conspiracy convictions without Ex Post Facto hesitation.
• Afford full deference to Sentencing Commission commentary, absent Supreme Court instruction to the contrary.
• Distinguish waiver from forfeiture with precision, thereby streamlining appellate review.

In short, Pugh is poised to shape sentencing litigation across the Seventh Circuit for years to come.