United States v. Edwards: Seventh Circuit Re-Defines the Boundaries of Appeal-Waiver Exceptions

1. Introduction

On 31 July 2025 the United States Court of Appeals for the Seventh Circuit decided United States v. Kenin Edwards, Nos. 24-2355 & 24-2401. Although the case began as a fairly typical tax-fraud prosecution, it evolved into a procedural labyrinth involving four successive defense attorneys, a mid-stream motion to proceed pro se, repeated efforts to withdraw a guilty plea, and a barrage of pro se filings. The appeal presented three issues:

Whether the district court violated Edwards’s Sixth-Amendment “choice-of-counsel” right by disqualifying attorney William Anderson for a conflict of interest;
Whether forcing (in Edwards’s view) the defendant to proceed pro se at sentencing infringed the right to counsel;
Whether the government breached the plea agreement by recommending a higher sentence than originally promised.

The Seventh Circuit did not reach the merits of any of these arguments. Instead, it dismissed the appeal outright on the ground that Edwards had executed a broad waiver of appellate rights in his written plea agreement—and none of the proffered arguments fit within the narrow exceptions recognized for such waivers.

2. Summary of the Judgment

Writing for a unanimous panel (Judges Ripple, Kirsch, and Kolar), Judge Kirsch reaffirmed three core propositions:

Appeal waivers in plea agreements are enforceable contracts and will be applied according to their plain terms;
The long-recognized “ineffective assistance” exception to an appeal waiver is limited to deficiencies occurring during the negotiation of the plea and waiver itself, not to later Sixth-Amendment complaints;
The circuit’s own precedent is divided on whether an alleged breach of a plea agreement automatically unlocks an otherwise valid appeal waiver, but under either line of authority Edwards’s claim failed because the government had not, in fact, breached.

Consequently, Edwards’s appeal was dismissed without reaching the substantive Sixth-Amendment or breach arguments.

3. Analysis

3.1 Precedents Cited

Garza v. Idaho, 586 U.S. 232 (2019) – confirmed that appeal waivers do not bar claims that fall outside their scope, especially those attacking the validity of the waiver itself.
United States v. Adkins, 743 F.3d 176 (7th Cir. 2014) – baseline enforceability of appeal waivers.
United States v. Bownes, 405 F.3d 634 (7th Cir. 2005) – constitutional limits on waiver; recognized exceptions for illegal sentences and ineffective assistance.
Elliott v. United States, 110 F.4th 974 (7th Cir. 2024) – held that a conflict-free-counsel argument falls within the ineffective-assistance exception when it undermines the voluntariness of the plea.
Whitlow v. United States, 287 F.3d 638 (7th Cir. 2002) & Hare, 269 F.3d 859 (2001) – stand for the proposition that once the district court finds no breach, a waiver prevents further appellate review.
Other Circuits: The opinion collects ten circuits that invalidate waivers when the government actually breaches (e.g., 4th Cir. Tate, 6th Cir. Keller).

3.2 Legal Reasoning

a. Scope of the Ineffective-Assistance Exception

Edwards argued that disqualifying Anderson denied him his “chosen counsel” and therefore should fit within the ineffective-assistance exception recognized in Elliott. The panel disagreed:

The right to choose counsel is distinct from the right to effective counsel; only the latter was previously recognized as overriding an appeal waiver when it taints the plea negotiations.
Edwards’s challenge did not allege that his guilty plea or waiver was involuntary; he affirmatively sought to keep the plea intact. Therefore, the waiver’s knowing and voluntary character remained unchallenged.
Structural error (which presumes prejudice) can still be waived; presumptive prejudice has no bearing on waiver enforceability.

b. Alleged “Forced” Self-Representation at Sentencing

The court treated this as a routine ineffective-assistance-at-sentencing complaint. Because the Faretta colloquy was thorough and the waiver preceded sentencing, the complaint had no effect on the plea’s validity and was therefore barred.

c. Government Breach Claim

The Seventh Circuit acknowledged its own “two lines” of precedent on breach-versus-waiver tension (the “two-step approach” vs. Whitlow/Hare). But it sidestepped the intra-circuit conflict because, under either approach, Edwards would lose: the government had not breached.

Key textual cues the court relied on:

The plea agreement gave the government complete discretion to withdraw the §3E1.1 acceptance-of-responsibility reduction if “new evidence” arose.
Edwards’s post-plea antics (recanting guilt, flooding the docket, alleging prosecutorial misconduct) provided that new evidence.
Once the reduction was withdrawn, the Guidelines range increased to 15–21 months, making a 21-month recommendation “squarely within the bargain” rather than a breach.

3.3 Impact of the Decision

Short-Term: The case closes one loophole defendants frequently try to exploit: re-characterizing post-plea Sixth-Amendment complaints as “ineffective-assistance” claims to evade an appeal waiver. The decision draws a clear line at when the alleged ineffective assistance must occur—during waiver negotiations.

Medium-Term: The Seventh Circuit leaves standing two inconsistent lines of precedent on plea-agreement breaches. While it did not resolve the split, it signaled that clarity may come in a future, cleaner case.

Long-Term / National: The opinion further cements a circuit split over whether a government breach invariably nullifies an appeal waiver. With ten circuits on one side (automatic nullification) and the Seventh offering mixed signals, the likelihood of Supreme Court review inches upward.

4. Complex Concepts Simplified

Appeal Waiver: Language in a plea agreement by which a defendant promises not to appeal the conviction or sentence. Think of it as a “no-return” policy on the deal.
Ineffective-Assistance Exception: A narrow rule allowing appeals when the lawyer who negotiated the plea performed so poorly that the defendant couldn’t make an informed, voluntary decision.
Structural Error: Errors so fundamental (e.g., exclusion of counsel at trial) that courts automatically assume prejudice and reverse; however, they can still be waived if the defendant knowingly signs away the right to complain.
Conflict-Free Counsel vs. Choice of Counsel: The Sixth Amendment guarantees an attorney free from conflicting loyalties and, to a lesser extent, the defendant’s preferred lawyer. Losing the preferred lawyer is not the same as being unrepresented or represented by a conflicted lawyer during plea bargaining.
Faretta Colloquy: A mandatory on-the-record conversation where the judge ensures a defendant understands the dangers of representing himself.

5. Conclusion

United States v. Edwards marks an important reaffirmation—and subtle recalibration—of the law surrounding appeal waivers in the Seventh Circuit. The court:

Tightened the ineffective-assistance exception, making clear it applies only to negotiating the plea and waiver, not to later Sixth-Amendment claims;
Clarified that structural errors, including choice-of-counsel violations, are still waivable;
Highlighted but did not resolve the circuit’s internal split on waiver-versus-breach jurisprudence, while illustrating a textual-contract approach that found no breach in Edwards’s case.

Practitioners should now assume that, in the Seventh Circuit, nearly all post-plea Sixth-Amendment complaints and “breach” allegations will be barred by a properly drafted waiver—unless they directly undermine the voluntariness of the plea itself.