Demasi and the Expansive Reach of Appeal Waivers: Sixth Circuit Bars Pre-Plea Constitutional Challenges on Direct Appeal

Introduction

In United States v. Anthony Demasi, No. 24-1806 (6th Cir. 2025), the Court of Appeals for the Sixth Circuit confronted a familiar but recurring problem: how far an appeal-waiver clause in a plea agreement reaches when a defendant attempts to raise constitutional and contractual claims on direct appeal.

Anthony Demasi, a highly educated entrepreneur with a prior commodities-fraud conviction, pleaded guilty to one count of bank fraud and one count of identity theft. His plea agreement contained both an appeal waiver (forbidding virtually all direct appeals) and a collateral-review waiver (limiting post-conviction challenges to very narrow grounds). After being sentenced to 12 months and one day—below the calculated Guidelines range—Demasi nevertheless filed a notice of appeal alleging prosecutorial misconduct, ineffective assistance of counsel, and unconscionability of his plea agreement.

The government moved to dismiss the appeal, invoking the waiver. The Sixth Circuit agreed, thereby reinforcing a stringent rule: when a plea agreement’s appeal waiver is knowing and voluntary, the waiver will foreclose even constitutional attacks on the conviction that pre-date the plea, forcing defendants to pursue such claims (if at all) via 28 U.S.C. § 2255.

Summary of the Judgment

• The panel (Judges Siler, Kethledge, and Bush) granted the government’s motion to dismiss and dismissed Demasi’s appeal in its entirety.
• The court applied de novo review to the validity of the waiver and found:
  • The claims asserted (prosecutorial misconduct, ineffective assistance, unconscionability) fall squarely within the scope of the waiver clause.
  • The waiver was entered knowingly and voluntarily, as confirmed by a meticulous Rule 11 colloquy.
  • Any exception preserved for sentencing did not apply because the sentence imposed did not exceed the top of the Guidelines range.
• Claims of ineffective assistance or prosecutorial misconduct may still be raised, but only in a § 2255 motion—not on direct appeal.

Analysis

1. Precedents Cited and Their Influence

The court relied heavily on prior Sixth Circuit jurisprudence defining the enforceability of waiver clauses:

• United States v. Smith, 344 F.3d 479 (6th Cir. 2003) – established de novo review for waiver validity.
• Portis v. United States, 33 F.4th 331 (6th Cir. 2022) – reaffirmed that constitutional rights may be waived if the waiver is knowing and voluntary.
• United States v. Milliron, 984 F.3d 1188 (6th Cir. 2021) – articulated the two-prong test: (1) scope and (2) knowing/voluntary nature.
• United States v. Toth, 668 F.3d 374 (6th Cir. 2012) – same two-prong test, applied to sentencing appeals.
• United States v. Lalonde, 509 F.3d 750 (6th Cir. 2007) and United States v. Abdulmutallab, 739 F.3d 891 (6th Cir. 2014) – guilty pleas waive most constitutional claims that precede the plea.
• Brady v. Maryland, 373 U.S. 83 (1963) – Demasi invoked Brady violations, but the panel held those claims barred by the waiver for direct-appeal purposes.
• United States v. Detloff, 794 F.3d 588 (6th Cir. 2015) and United States v. Lopez-Medina, 461 F.3d 724 (6th Cir. 2006) – ineffective-assistance claims ordinarily reserved for § 2255 proceedings where a fuller record can be developed.

By harmonizing these decisions, the panel presented a clear, chronological chain of authority that compelled dismissal.

2. Core Legal Reasoning

1. Scope of the Waiver: The clause barred “any” appeal of the conviction, and permitted a sentencing appeal only if the sentence exceeded the Guideline maximum. Demasi’s sentence did not, thus the gateway was closed.
2. Knowing and Voluntary Standard:
   • Review of the Rule 11 colloquy confirmed that the magistrate judge explained both the direct-appeal waiver and the collateral-review limits.
   • Demasi repeatedly acknowledged understanding and acceptance.
   • No contemporaneous objections or confusion appeared in the record.
3. Pre-Plea Constitutional Violations:
   • Even if Brady or other misconduct occurred, those claims are waived by a valid guilty plea (Lalonde; Abdulmutallab).
   • Because the plea agreement did not reserve such issues for appeal, the waiver is controlling.
4. Unconscionability Argument Rebuffed:
   • The agreement allowed the government to advocate for any lawful sentence; hence its conduct at sentencing did not breach the deal.
   • No legal authority supplied for labeling the contract unconscionable.
5. Channeling of Claims: The panel emphasized that Demasi still possesses avenues of relief—namely § 2255—preserving judicial economy while honoring the bargain struck.

3. Potential Impact of the Decision

This unpublished opinion nevertheless cements a practical rule of thumb in the Sixth Circuit:

The ruling’s ripple effects include:

• Greater Finality of Plea Agreements: Prosecutors and district courts can rely on the finality of waivers, reducing appellate litigation.
• Heightened Defense-Counsel Duties: Attorneys must meticulously explain the difference between direct appeal and collateral review, or risk later ineffective-assistance claims.
• Strategic Choices for Defendants: Defendants must decide whether to insist on preserving certain issues for appeal before signing any agreement.
• Uniformity Across Circuits: The decision aligns the Sixth Circuit with others (e.g., the Fifth, Seventh, and Eleventh) that broadly enforce such waivers, thereby promoting doctrinal consistency.

Complex Concepts Simplified

• Plea Agreement: A contract between the defendant and the government: the defendant pleads guilty; the government often drops charges or makes sentencing concessions.
• Appeal Waiver: A clause whereby the defendant relinquishes the right to appeal the conviction and/or sentence, either in whole or in part.
• Collateral Review: A separate, post-conviction process (often via § 2255) allowing defendants to challenge the legality of their detention based on constitutional or jurisdictional defects.
• Rule 11 Colloquy: The district court’s required, on-the-record dialogue with the defendant ensuring the plea is voluntary, informed, and factual basis exists.
• Guidelines Range: The advisory sentencing range generated by the U.S. Sentencing Guidelines; often used as a benchmark for whether a waiver permits sentencing appeals.
• Brady Violation: The prosecution’s failure to disclose materially exculpatory evidence; ordinarily grounds for reversal, but waivable.

Conclusion

United States v. Demasi solidifies the Sixth Circuit’s stringent enforcement of appeal waivers in plea agreements. The court held that a comprehensive waiver, coupled with a clear Rule 11 inquiry, forecloses direct appellate review of both constitutional and contractual claims arising before the guilty plea. Defendants are steered toward § 2255 as the exclusive channel for residual allegations of prosecutorial misconduct or ineffective assistance. The decision underscores the importance of (1) meticulous drafting of waiver clauses, (2) scrupulous judicial colloquies, and (3) fully informed decision-making by defendants and counsel alike. In the broader legal landscape, Demasi promotes finality in criminal proceedings while preserving limited, but vital, collateral remedies for extraordinary errors.