“Manager or Supervisor” Under U.S.S.G. § 3B1.1(c) Means Oversight—And Application Note 4 Cannot Supply the Rule Absent Genuine Ambiguity

Case: United States v. Timothy Riddy (3d Cir. July 1, 2026) (precedential)

1. Introduction

United States v. Timothy Riddy addresses a recurring post-Kisor sentencing question: when may a district court rely on the Sentencing Guidelines’ commentary to define a key guideline term? The appeal arose from a cocaine conspiracy in Monroe County, Pennsylvania, involving Timothy Riddy and codefendant Steven Brown. The core sentencing dispute was whether Riddy qualified as a “manager” or “supervisor” under U.S.S.G. § 3B1.1(c), triggering a two-level aggravating-role enhancement.

The stakes were unusually high because the enhancement affected statutory-minimum sentencing. With the enhancement, Riddy became ineligible for the “safety valve” (18 U.S.C. § 3553(f)(4)), preventing the District Court from sentencing below the ten-year mandatory minimum under 21 U.S.C. § 841(b)(1)(A). Without the enhancement, he could have been eligible for relief below 120 months.

2. Summary of the Opinion

The Third Circuit affirmed the 120-month sentence but did so while correcting the legal framework:

• The District Court erred by consulting the commentary (specifically Application Note 4 to § 3B1.1) without first performing the ambiguity analysis required by United States v. Nasir.
• Nevertheless, the error was harmless under Fed. R. Crim. P. 52(a) because, applying the correct post-Kisor/Nasir approach, the guideline text itself is not genuinely ambiguous and the record supported the enhancement.
• The court held that, as used in § 3B1.1(c), a “manager” or “supervisor” is a person with oversight over operations or other persons.

3. Analysis

3.1. Precedents Cited

United States v. Nasir, 17 F.4th 459 (3d Cir. 2021) (en banc)

• The doctrinal anchor of the opinion. Nasir applied Kisor to the Sentencing Guidelines and adopted a structured inquiry before deferring to commentary.
• In Riddy, the Third Circuit faulted the District Court for skipping this threshold “genuine ambiguity” step—then proceeded to perform it on appeal.

Kisor v. Wilkie, 588 U.S. 558 (2019)

• The Supreme Court limited deference to an agency’s interpretation of its own regulation to circumstances where the regulation is “genuinely ambiguous,” after rigorous interpretive work.
• Riddy treats the Sentencing Commission commentary similarly: it cannot be used to expand or effectively rewrite clear guideline text.

United States v. Metro, 882 F.3d 431 (3d Cir. 2018) and Stinson v. United States, 508 U.S. 36 (1993)

• These decisions reflect the pre-Kisor era, under which commentary was treated as authoritative unless inconsistent with the guideline.
• Riddy situates its holding as part of the Third Circuit’s transition away from broad, near-automatic commentary deference.

United States v. Chandler, 104 F.4th 445 (3d Cir. 2024)

• Supplies a key refinement of step two of the Nasir/Kisor framework: commentary is “reasonable” only if it clarifies an identified ambiguity without changing the text’s meaning.
• In Riddy, this mattered because Application Note 4’s multi-factor test could not be treated as controlling if the guideline text is unambiguous.

United States v. Adair, 38 F.4th 341 (3d Cir. 2022)

• The opinion’s principal interpretive template. Adair used contemporaneous dictionary definitions and structural context to construe role terms in § 3B1.1.
• Riddy extends Adair’s method to the terms “manager” and “supervisor,” and also repeats Adair’s important distinction: courts may consider certain “background” commentary without running the full Kisor analysis, because it is not interpretive gloss on a contested term.

Perrin v. United States, 444 U.S. 37 (1979)

• Provides the interpretive default rule applied here: undefined, non-technical words generally take their “ordinary, contemporary, common meaning.”

Anderson v. City of Bessemer City, 470 U.S. 564 (1985)

• Supplies the articulation of “clear error” review for factual findings supporting the enhancement, reinforcing the deferential posture on the District Court’s factfinding.

United States v. McIntosh, 124 F.4th 199 (3d Cir. 2024) and United States v. Miller, 172 F.4th 242 (3d Cir. 2026)

• These cases supply the standards of review: de novo for guideline interpretation (McIntosh) and clear error for the enhancement’s factual predicates (Miller).

3.2. Legal Reasoning

The court’s reasoning proceeds in two layers: (1) interpretive method (when commentary matters), and (2) substantive meaning (what “manager/supervisor” means).

(1) The interpretive method (the Nasir gatekeeping requirement)

• The District Court consulted Application Note 4 “for some guidance” without first deciding whether § 3B1.1(c)’s terms were ambiguous.
• Under Nasir (implementing Kisor), that is backwards: a court must exhaust traditional interpretive tools and find “genuine ambiguity” before using commentary as an authoritative gloss.

(2) The substantive meaning (ordinary meaning + structure + purpose)

• Because “manager” and “supervisor” are not guideline-defined and are not treated as specialized terms of art, the court adopted ordinary meanings drawn from contemporaneous dictionaries (as in United States v. Adair), equating both terms with oversight over operations or persons.
• Textual/structural cues reinforced that reading:
  • The use of “an” suggests multiple people can qualify as managers/supervisors in the same scheme (not a singular, exclusive role).
  • The “or” connector was read as linking similar terms rather than establishing sharply distinct categories.
  • The three-tier structure of § 3B1.1 (a)/(b)/(c) implies gradations of responsibility: “organizer/leader” reflects greater culpability; “manager/supervisor” requires a lesser—but still real—degree of operational control.
• Purpose, drawn from the Background to § 3B1.1, supported the hierarchy: offense levels rise with “the size of the organization and the degree of the defendant’s responsibility.”
• History offered little interpretive help (only a non-substantive amendment in 2024), so the ordinary-meaning approach remained primary.

Harmless error

• Even though the District Court used the wrong framework, the Third Circuit applied Fed. R. Crim. P. 52(a) and held the error harmless because the unambiguous text—properly understood—still covered Riddy’s conduct.
• The record supported “oversight” of both a participant (Brown) and operations: Riddy controlled the Cash App payments, directed Brown to complete deliveries, used his vehicle, and controlled credit/fronting decisions and payment confirmation via texts.

3.3. Impact

The decision’s practical and doctrinal impacts are significant in the Third Circuit:

• Clarified meaning of “manager/supervisor” under § 3B1.1(c): The operative concept is oversight over operations or other persons, grounded in ordinary meaning and structural hierarchy—without the need to resort to Application Note 4’s factor list.
• Reduced centrality of Application Note 4 in litigation: Parties may still cite the note as “guidance,” but Riddy signals that it cannot be treated as controlling where the text is clear. Future briefing is likely to pivot toward concrete proof of “oversight” rather than checklists.
• Safety-valve consequences will sharpen fact disputes: Because § 3553(f)(4) turns on leadership-role findings, the government and defendants will likely focus on building (or undermining) a record of operational direction, delegation, or control.
• Appellate posture on sentencing errors: The case also demonstrates a path to affirmance through harmless-error analysis even when a district court fails to perform the Nasir sequencing—so long as the record independently satisfies the unambiguous guideline standard.

4. Complex Concepts Simplified

• “Guidelines commentary”: Notes written by the Sentencing Commission that explain how to apply guideline provisions. After Kisor and United States v. Nasir, courts in the Third Circuit treat commentary like an agency interpretation: it matters only if the guideline text is genuinely unclear.
• “Genuinely ambiguous”: Not just “debatable.” A guideline is genuinely ambiguous only after a court uses traditional tools—text, structure, history, and purpose—and still cannot resolve the meaning.
• “Manager or supervisor” (§ 3B1.1(c)): In this opinion, the terms mean someone who has oversight—either over other people in the crime or over how the criminal operation runs (e.g., directing deliveries, controlling payment channels, approving credit).
• “Safety valve” (18 U.S.C. § 3553(f)): A statutory mechanism allowing some drug defendants to receive a sentence below an otherwise mandatory minimum if several criteria are met. One disqualifier is having an aggravating role (here, § 3553(f)(4)).
• “Harmless error” (Fed. R. Crim. P. 52(a)): Even if a court makes a legal mistake, an appellate court can affirm if the mistake did not affect the defendant’s substantial rights—here, because the same enhancement applied under the correct legal standard.

5. Conclusion

United States v. Timothy Riddy reinforces and extends the Third Circuit’s post-Kisor, post-Nasir approach to the Sentencing Guidelines: commentary does not control unless the guideline text is genuinely ambiguous. On the merits, the court held that “manager” and “supervisor” in § 3B1.1(c) are unambiguous ordinary terms centered on oversight of people or operations. Although the District Court erred by turning to Application Note 4 without first performing the Nasir analysis, the error was harmless because the record showed Riddy directed and controlled key aspects of the conspiracy, supporting the enhancement—and foreclosing safety-valve relief.