The Wilson Clarification: Plea Stipulations Alone Do Not Restrict Government Sentencing Advocacy Absent Explicit Limits

Introduction

In United States v. William Dayshawn Wilson, a published decision of the U.S. Court of Appeals for the Fourth Circuit (Aug. 25, 2025), the court addressed an increasingly common flashpoint in federal plea practice: how far the government may go at sentencing when a plea agreement contains Guidelines stipulations but also reserves broad sentencing-advocacy rights. Writing for the majority, Judge Jasmine H. Yoon (joined by Chief Judge Diaz) affirmed a 234-month sentence over a claim that the government breached the plea agreement by (1) not seeking a below-Guidelines sentence and (2) arguing upward based on facts seemingly inconsistent with the parties’ stipulations to drug weight and role. Judge Gregory dissented.

The case crystallizes the interaction between (a) stipulations to discrete Guidelines factors, (b) broad “reservation-of-rights” language, including reliance on 18 U.S.C. § 3661 to present any information about the defendant’s background and conduct, and (c) the demanding plain-error standard that applies when alleged breaches are not preserved below. It simultaneously reinforces the Fourth Circuit’s recent trajectory in United States v. Johnson (2024) and cabins the reach of United States v. Edgell (2019).

Summary of the Judgment

The court affirmed Wilson’s 234-month sentence under plain-error review.
There was no plain error in the government’s failure to request a below-Guidelines sentence; the plea agreement expressly stated the government was “not promising to move for [a] departure” and reserved the right to make a sentencing recommendation.
There was no plain error in the government’s upward-sentencing advocacy that referenced conduct arguably exceeding the parties’ stipulations (larger-scale drug activity and leadership beyond a “manager or supervisor” enhancement). Given the agreement’s broad reservations (including § 3661) and the absence of an explicit promise to recommend a sentence within the stipulated range, any breach was not “clear or obvious” under current law.
Edgell was distinguished: unlike in Edgell, Wilson’s plea contained no commitment by the government to recommend a sentence at the low end of the Guidelines range that flowed from the stipulations.
Judge Gregory dissented, reading the agreement (and Fourth Circuit principles construing ambiguity against the government) to require resentencing even under plain-error review.

Factual and Procedural Background

Charge: Aiding and abetting possession with intent to distribute 40+ grams of a fentanyl mixture (21 U.S.C. § 841(a)(1); 18 U.S.C. § 2).
Plea Agreement: The government stipulated (i) to a converted drug weight yielding a base offense level of 24 and (ii) that Wilson was a “manager or supervisor” under U.S.S.G. § 3B1.1(b). The agreement reserved the government’s right to make a sentencing recommendation, present any information under 18 U.S.C. § 3661, and it expressly stated the government was “not promising to move for [a] departure.”
PSR: Attributed substantially more relevant conduct (multi-kilogram drug quantities; a potential “organizer or leader” role), producing an advisory range that would have been life (capped by statute at 480 months) if adopted. The probation officer separately calculated the range corresponding to the stipulations as 188–235 months (total offense level 32, CHC V).
Sentencing: The district court used the stipulation-based range (188–235) as the starting point, granted the government’s motion for an upward departure (to offense level 33/CHC VI, 235–293), granted the government’s motion for a downward departure, and imposed 234 months.
Appeal: Wilson argued breach of the plea agreement based on (1) the government’s failure to request a below-Guidelines sentence and (2) reliance on facts inconsistent with the stipulations. No objection was made below; review was for plain error.

Analysis

Precedents Cited and Their Influence

Santobello v. New York, 404 U.S. 257 (1971): A prosecutor must fulfill promises constituting part of the inducement for a guilty plea. The majority invokes this baseline but asks whether any such promise was actually made here.
United States v. Peglera, 33 F.3d 412 (4th Cir. 1991): The government is held only to promises it actually made; no party is obligated to provide more than specified. This frames the majority’s contract-law reading of the plea’s plain text.
United States v. Tate, 845 F.3d 571 (4th Cir. 2017): Plea agreements are interpreted by their plain language, giving effect to all provisions. The majority enforces the reservation-of-rights clauses as written.
United States v. Johnson, 119 F.4th 343 (4th Cir. 2024): Where materially identical reservation language existed, the government’s advocacy for a sentence above the guideline range calculated from stipulations did not breach the plea, absent a promise to recommend within that range. The majority leans heavily on Johnson to validate the scope of the government’s advocacy.
United States v. Batts, 317 F. App’x 329 (4th Cir. 2009): No breach where the government moved for an upward departure and the agreement contained no prohibition on doing so. Supports the government’s ability to seek an upward departure absent contrary terms.
United States v. Snow, 234 F.3d 187 (4th Cir. 2001): The government does not waive the ability to seek an upward departure absent an explicit waiver. Rebuts the argument that moving downward forecloses moving upward.
United States v. Edgell, 914 F.3d 281 (4th Cir. 2019): Where the government stipulated to drug quantity and promised to recommend the low end of the resulting range, advocating within a higher range breached the plea. The majority distinguishes Edgell because no such recommendation promise existed here; the dissent reads Edgell more broadly as protecting the value of factual stipulations.
United States v. Munoz, 408 F.3d 222 (5th Cir. 2005): The government may not hide behind its duty of candor to circumvent plea commitments. Quoted in Edgell and acknowledged here; the majority concludes the government’s language-triggered discretion makes any breach not “plain.”
United States v. Dawson, 587 F.3d 640 (4th Cir. 2009): Sets the plain-error standard and confirms that appeal waivers do not bar breach claims. Controls the standard of review.
Puckett v. United States, 556 U.S. 129 (2009): Not all plea breaches are plain; the plain-error inquiry is case-specific and law-dependent. Central to the majority’s “no clear or obvious error” conclusion.
United States v. Hope, 28 F.4th 487 (4th Cir. 2022): Plain error must be clear or obvious under current law. Supports the majority’s hesitancy to find plain error in an agreement with broad reservation clauses.

Legal Reasoning

The majority proceeds from basic contract principles applied to plea agreements, tempered by heightened scrutiny because constitutional rights are at stake. It asks two questions: What did the government promise, as a matter of contract? And even if the government’s conduct is “troubling,” was any breach “plain” under existing law?

On the first alleged breach—failure to request a below-Guidelines sentence—the agreement explicitly stated the government was “not promising to move for [a] departure” and reserved the right to make a sentencing recommendation. The government actually did more than it promised by filing a motion for a downward departure, while also seeking an upward departure/variance based in part on criminal history. Nothing in the agreement prohibited simultaneous upward and downward requests, and the Fourth Circuit’s cases (Johnson, Batts, Snow) confirm that absent explicit restrictions, the government’s advocacy latitude remains broad.

On the second alleged breach—using facts arguably inconsistent with stipulations—the court acknowledges “tension” between the government’s rhetoric (Wilson “running” drug houses, “leadership in the gang,” “orchestration,” “huge amounts of money”) and the plea’s stipulations (drug weight yielding base level 24; role capped at “manager or supervisor”). However, the agreement also:

Reserved the right to present any information pursuant to 18 U.S.C. § 3661 (which allows a sentencing court to consider any information about the defendant’s background, character, and conduct),
Reserved the right to make a sentencing recommendation and offer argument, and
Did not require a recommendation within the stipulated range or preclude argument for a variance or departure above that range.

Given these reservations, and the absence of any explicit promise like the one in Edgell (to recommend the low end of the range produced by the stipulations), the majority concludes any breach is not “clear or obvious” under current Fourth Circuit and Supreme Court law. The government also did not ask the court to apply different Guidelines than those stipulated; it argued for departures/variance in light of broader conduct. Under Puckett, where obligations are “open to doubt,” breach is not plain.

The court flags the policy concern: if stipulations constrain only the initial Guidelines calculation but permit the government to advocate upward by invoking broader facts, the “benefit” of stipulations can be diluted. But that concern goes to drafting; it does not transform the government’s advocacy here into plain error.

The Dissent’s View

Judge Gregory agrees the government’s conduct is “troubling,” but would find plain error and remand for resentencing. He emphasizes:

The integrity of the plea-bargaining system depends on good faith; ambiguities are construed against the government as the drafter (citing Petties, Barefoot, Wood).
Fact-based stipulations to offense levels implicitly restrain contradictory advocacy; the government’s reliance on broader drug quantities and leadership to secure an upward departure undermined the bargain’s core benefit.
Prejudice and the fourth prong of plain error are satisfied because the court might not have departed upward had the government honored the stipulations, and government breach “seriously affects the fairness, integrity, or public reputation of judicial proceedings” (quoting Edgell and Puckett).
Case-specific circumstances (change of counsel and failure to preserve) should not insulate a breach undermining the plea’s integrity.

Impact and Practical Implications

This published decision is an important clarification for the Fourth Circuit:

Reservation clauses matter. Where a plea agreement reserves the government’s right to present “any information” under § 3661 and to make a sentencing recommendation—and does not expressly promise to recommend within a stipulated range—the government may advocate for upward departures/variances even when that advocacy creates “tension” with Guidelines stipulations.
Stipulations are not self-executing gag orders. Absent explicit language, stipulations to drug quantity or role do not silently bar the government from presenting broader relevant conduct at sentencing or from urging an upward variance.
Preservation is critical. Alleged breaches must be objected to at sentencing to avoid the formidable plain-error standard. Even “troubling” conduct will often not be “plain” where the agreement includes broad reservation language.
Drafting discipline is decisive. If defendants seek to constrain the government’s sentencing advocacy, they must negotiate explicit commitments, such as:
- The United States will recommend a sentence within—and at the low end of—the Guideline range produced by the stipulated offense levels.
- The United States will not seek any upward departure or variance.
- The United States will not present or argue facts inconsistent with the factual stipulations for any departure or variance purpose.
- Limitations or tailoring of § 3661 language (for example, agreeing that the government will furnish materials to probation but will not rely on non-stipulated relevant conduct to seek a higher sentence).
Prosecutorial caution remains wise. The court notes the risk of “misleading defendants” where stipulations are later sidestepped in advocacy. Even if not “plain error,” prosecutors should balance candor and commitments by continuing to “advocate for acceptance of the agreement” (per Edgell), and avoid rhetoric that appears to convert a “manager/supervisor” stipulation into an “organizer/leader” case by another name.
Contours of Edgell and Johnson. The case harmonizes these decisions: Edgell controls when the government promises a specific recommendation tethered to the stipulated range; Johnson applies where the government made no such promise and retained broad sentencing-advocacy rights.

Complex Concepts Simplified

Plain error review: Applies when an issue was not preserved below. The appellant must show (1) error, (2) that is clear or obvious, (3) affecting substantial rights (prejudice), and (4) seriously affecting the fairness, integrity, or public reputation of judicial proceedings.
Guidelines “stipulations”: Plea-agreement provisions where parties agree to certain Guidelines factors (like drug weight or role). They typically inform the advisory range but do not bind the court unless the plea is of a type that binds the court (e.g., Rule 11(c)(1)(C) agreements).
Departure versus variance: A departure is a Guidelines-authorized adjustment (e.g., criminal history inadequacy under U.S.S.G. § 4A1.3). A variance is a non-Guidelines adjustment based on 18 U.S.C. § 3553(a) factors.
18 U.S.C. § 3661: Provides that no limitation shall be placed on the information the sentencing court may receive and consider about a convicted person’s background, character, and conduct. Pleas often incorporate this concept to permit broad advocacy.
U.S.S.G. § 3B1.1 roles: “Organizer/leader” (4-level enhancement) versus “manager/supervisor” (3-level). Distinctions turn on decision-making authority, recruitment, planning, control, and the number of participants.
Construing ambiguity against the drafter: In plea agreements, ambiguities are generally construed against the government as drafter. The dissent would have applied this principle to find a breach; the majority concluded any breach was not “plain” in light of the agreement’s express reservations and current case law.
Appeal waivers and breach: A defendant’s waiver of appellate rights does not bar claims that the government breached the plea agreement, but unpreserved breach claims face plain-error review.

Key Takeaways

In the Fourth Circuit, plea stipulations to Guidelines components do not, by themselves, restrict the government’s sentencing advocacy where the agreement reserves § 3661 rights and contains no explicit promise to recommend within the stipulated range.
To meaningfully cabin the government’s ability to argue upward based on broader relevant conduct, defense counsel must secure express, unambiguous limits in the plea agreement.
Defense counsel must object contemporaneously to any perceived breach to avoid the steep hurdles of plain-error review.
The decision leaves room for a different outcome if a breach is preserved or if the plea contains more specific government commitments (as in Edgell).

Conclusion

United States v. Wilson is a consequential, published clarification of plea-agreement dynamics in the Fourth Circuit. It reaffirms that, absent explicit contractual limits, the government’s broad reservation-of-rights—especially a § 3661 clause—permits robust sentencing advocacy, including arguments for upward departures or variances grounded in relevant conduct beyond the stipulations. At the same time, the court underscores the need for careful drafting: if defendants want the benefit of stipulations to extend beyond the Guidelines calculation and constrain the government’s advocacy, those limits must be said, not assumed. Finally, the case is a cautionary tale on preservation: even “troubling” government tactics will be hard to undo on appeal under the plain-error standard. The dissent’s forceful reminder about good faith and the integrity of pleas ensures the debate will continue, but Wilson sets the operative rules for now.