Enforceability of Appeal Waivers in Plea Agreements: Scope and Limited Exceptions under Second Circuit Jurisprudence

Introduction

United States v. Graham, No. 24-292 (2d Cir. Apr. 21, 2025) addresses the enforceability of an appeal waiver in a federal plea agreement and clarifies the narrow circumstances under which such waivers may be set aside. Defendant‐Appellant Lairon Graham (“Graham”) pleaded guilty in the Western District of New York to fentanyl distribution conspiracy and multiple counts of sex trafficking by force or coercion. He received a 264-month prison sentence plus a ten-year term of supervised release, and later had his prison term commuted to 150 months. On appeal, Graham argued that his counsel was ineffective for stipulating that a prior state robbery conviction qualified as a “serious violent felony,” thereby triggering a lengthy supervised‐release term. The Second Circuit dismissed Graham’s appeal, holding that his knowing, voluntary waiver of appellate and collateral rights encompassed his claim, and that he had not shown any exception rendering the waiver unenforceable.

Summary of the Judgment

The Second Circuit, in a summary order, dismissed Graham’s appeal. The court reaffirmed that:

A valid, knowing, and voluntary appeal waiver in a plea agreement is presumptively enforceable.
Such waivers can only be set aside in narrowly defined circumstances, including waivers procured by counsel’s ineffectiveness with respect to the waiver itself, or where a sentence rests on constitutionally impermissible factors.
Graham’s plea agreement expressly waived his right to appeal or collaterally attack any sentence of up to life imprisonment and ten years of supervised release “notwithstanding the manner in which the Court determines the sentence.”
Graham did not contend that the waiver was unknowing or involuntary, nor did he show any breach by the government, racial bias in sentencing, or lack of district court reasoning.
His ineffective‐assistance claim focused on counsel’s stipulation of a prior conviction’s character, not on counsel’s adequacy in negotiating or explaining the waiver itself.

On that basis, the court enforced the appeal waiver and declined to address the merits of Graham’s ineffective‐assistance claim, dismissing the appeal in full.

Analysis

1. Precedents Cited

United States v. Ojeda, 946 F.3d 622 (2d Cir. 2020) – Affirms that a “knowing and voluntary” waiver of appellate rights is presumptively enforceable.
United States v. Borden, 16 F.4th 351 (2d Cir. 2021) – Emphasizes the “very circumscribed area” in which courts will refuse to enforce an appeal waiver.
United States v. Yemitan, 70 F.3d 746 (2d Cir. 1995) – Explains the practical importance of waivers as bargaining tools, and why breaking them undermines plea‐bargaining integrity.
Cook v. United States, 84 F.4th 118 (2d Cir. 2023) – Lists the limited categories justifying waiver unenforceability, including involuntariness, unlawful sentencing factors, government breaches, lack of court rationale, or no consideration.
United States v. Oladimeji, 463 F.3d 152 (2d Cir. 2006) – Describes the “provisional enforcement” rule for ineffective‐assistance‐of‐counsel claims that arise after entry of a plea.
United States v. Monzon, 359 F.3d 110 (2d Cir. 2004) – Holds that a waiver is unenforceable only if the record plainly shows the waiver itself was the result of ineffective assistance.
Pulsifer v. United States, 601 U.S. 124 (2024) – Guides contextual interpretation of contract language (such as “and” vs. “or”) to effectuate the parties’ intent.

2. Legal Reasoning

The Court applied a two‐step analysis:

Validity of the Waiver: Graham’s written plea agreement explicitly and unambiguously waived “the right to appeal and collaterally attack any component of a sentence” within defined bounds. There was no allegation that the plea colloquy or agreement was deficient, nor that counsel’s performance undermined Graham’s understanding of the waiver itself.
Scope of Exceptions: Under Cook, only five exceptional circumstances can void a waiver. Graham alleged ineffective assistance relating to sentencing strategy, not ineffective assistance in connection with the waiver. Thus, his argument fell squarely within the scope of his own waiver.

Because Graham did not—and could not—show that the waiver was unknowing, involuntary, or otherwise invalid, the Court enforced it and declined to reach the substantive ineffective‐assistance claim.

3. Impact on Future Cases

United States v. Graham reinforces several critical points for practitioners and defendants:

Firmness of Waivers: Well‐drafted appeal waivers will be enforced unless a defendant can show a narrow exception.
Strategic Trade-Offs: Defendants must understand that raising sentencing or counsel‐performance issues post–plea may be foreclosed if covered by a waiver.
Crafting Plea Agreements: Defense counsel must ensure that defendants knowingly and competently waive rights, and that any carve-outs for ineffective assistance are carefully tailored.
Courtroom Practice: District courts should continue to conduct thorough colloquies to confirm that plea waivers are voluntary and informed.

Complex Concepts Simplified

Appeal Waiver: A contractual provision in a plea agreement where the defendant gives up the right to challenge their sentence on appeal or through collateral proceedings, provided certain conditions are met.
Ineffective Assistance of Counsel: A constitutional claim under the Sixth Amendment in which a defendant argues that their lawyer’s performance fell below an objective standard of reasonableness and prejudiced the outcome.
Summary Order: A non-precedential appellate decision resolving an appeal without a full published opinion, though it remains binding on the parties and provides guidance on similar issues.
Collateral Attack: A challenge to a conviction or sentence made outside the direct‐appeal process, typically through habeas corpus proceedings.
“Presumptively Enforceable”: The default rule that a valid waiver is accepted unless a defendant can meet a high bar to prove an exception applies.

Conclusion

United States v. Graham crystallizes the Second Circuit’s staunch support for enforcing appeal waivers contained in plea agreements, while delineating the very limited exceptions that might void them. The case underscores the importance of ensuring that defendants enter into waivers knowingly and that counsel adequately explains their consequences. Going forward, both defense attorneys and prosecutors will rely on this decision to negotiate and draft plea agreements, and district courts will look to it when assessing the validity and scope of appeal waivers. Ultimately, Graham reaffirms the balance between efficient resolution of cases through plea bargains and preserving the fundamental right to challenge one’s conviction or sentence under truly exceptional circumstances.