Background
Timothy Riddy and Steven Brown distributed cocaine base in Monroe County, Pennsylvania. DEA agents arranged controlled purchases between May and September 2024, during which Brown—driving Riddy’s vehicle—made three deliveries. Search warrant execution at Riddy’s residence yielded cocaine, a drug ledger, and over $2,000 in cash. Cash App records showed approximately $180,000 in payments to Riddy from customers.
Riddy pleaded guilty to conspiracy to distribute cocaine in June 2025. The Presentence Report recommended a 2-level leadership enhancement under U.S.S.G. § 3B1.1(c), deeming Riddy a “manager” or “supervisor” of criminal activity. With the enhancement, Riddy’s guideline range was 120–135 months. Without it, he would have qualified for the safety valve exception to the statutory 10-year minimum. The District Court applied the enhancement and sentenced him to 120 months. Riddy appealed.
The Court’s Holding
The Third Circuit held that the District Court erred by deferring to Sentencing Guidelines commentary without first determining whether the guideline text was genuinely ambiguous. Under Supreme Court precedent in Kisor v. Wilkie and Third Circuit precedent in United States v. Nasir, courts may consult and defer to Sentencing Commission commentary only where the guideline itself is genuinely ambiguous. The court must follow a three-step analysis: (1) determine genuine ambiguity by carefully examining text, structure, history, and purpose; (2) if ambiguous, assess whether the commentary is reasonable; and (3) if reasonable, determine whether it is entitled to controlling weight.
The court concluded that the terms “manager” and “supervisor” in § 3B1.1(c) are not genuinely ambiguous. Using ordinary contemporary meaning at the time of promulgation, “manager” and “supervisor” both mean a person with oversight over operations or other persons. The structure of § 3B1.1—with subsections (a), (b), and (c) providing different enhancements—shows that managers and supervisors occupy a lower position in the culpability hierarchy than organizers and leaders. Therefore, the District Court should not have consulted Application Note 4 without this foundational analysis.
However, the legal error was harmless. The record clearly demonstrated that Riddy had oversight over both Brown and the drug operations: Riddy directed whether Brown would conduct transactions, controlled the Cash App payment system, decided whether to front drugs on credit, and confirmed customer payments before delivery. This evidence sufficed to establish Riddy as a manager or supervisor under the plain text of the guideline.
Key Takeaways
- District courts must conduct a genuine ambiguity analysis under Kisor and Nasir before consulting Sentencing Guidelines commentary; defaulting to commentary without this analysis is legal error.
- The terms “manager” and “supervisor” in § 3B1.1(c) are not ambiguous and mean a person with oversight over operations or persons—a position less culpable than organizer or leader.
- Evidence of oversight (directing another’s conduct, controlling critical operational elements like payments, or making discretionary operational decisions) can establish manager or supervisor status for sentencing enhancement purposes.
Why It Matters
This decision reinforces the post-Kisor framework for interpreting Sentencing Guidelines in the Third Circuit and places heightened procedural demands on sentencing judges. Judges can no longer treat commentary as a shortcut to guideline interpretation; they must first examine the text’s ordinary meaning. For practitioners, the decision provides grounds to challenge enhancements based on improperly consulted commentary, though harmless error analysis may still sustain sentences where the underlying facts support the enhancement.
The ruling has broader implications for other Guidelines enhancements relying on undefined terms such as “leader” or “organizer.” Courts must now apply ordinary meaning and structural analysis rather than deferring to interpretive commentary. In conspiracy and organizational crime cases, the decision clarifies that oversight need not be absolute control—directing others’ actions, managing payment systems, and making operational decisions suffice to establish supervisory status for sentencing purposes.