United States v. Windham: Second Plea Hearing as Cure for Judicial Participation Errors and the Breadth of Sentence Appeal Waivers

Introduction

United States v. Eric Alonzo Windham, No. 22-11622 (11th Cir. Jan. 2, 2025), addresses the interaction of Federal Rule of Criminal Procedure 11 with plea-hearing procedure, the “safety valve” in federal sentencing, the plain-error standard on appeal, and the enforceability of sentence appeal waivers. The defendant, Eric Alonzo Windham, was charged with conspiracy to possess with intent to distribute more than five kilograms of cocaine. He went through two plea hearings before entering his final guilty plea, challenged the voluntariness of that plea based on alleged judicial participation in negotiations and misinformation about safety valve eligibility, moved to suppress evidence, and objected at sentencing that discretionary conditions of supervised release were not orally announced. On appeal, the Eleventh Circuit affirmed in full.

Summary of the Judgment

The Court of Appeals held:

No plain error occurred in the plea negotiations: Although the first plea hearing included improper judicial comments about sentencing options, that hearing did not culminate in a plea, a week later a different judge conducted a full Rule 11 colloquy, and the second plea was knowing, voluntary, and uncoerced.
The defendant’s guilty plea was knowing and voluntary under Rule 11 despite prior comments about safety valve eligibility, because the second hearing, the plea agreement and colloquy addressed all core Rule 11 concerns, and no “reasonable probability” existed that Windham would have gone to trial.
He waived any challenge to the denial of his suppression motion by pleading unconditionally; no conditional plea preserved that issue.
The sentence appeal waiver in his plea agreement bars his due-process claim that the district court failed to orally pronounce discretionary supervised-release conditions, even though the written judgment included them.

Analysis

Precedents Cited

Rule 11 Participation Prohibition: Corbitt (996 F.2d 1132), Casallas (59 F.3d 1173), Davila (569 U.S. 597).
Second Plea Hearing Cures: Casallas v. United States, 59 F.3d 1173 (11th Cir. 1995).
Plain-Error Standard: Monroe (353 F.3d 1346), Castro (736 F.3d 1308), Cruickshank (837 F.3d 1182).
Plea Voluntariness & Core Rule 11 Principles: Dominguez Benitez, 542 U.S. 74; Moriarty (429 F.3d 1012); Telemaque (244 F.3d 1247).
Plea Agreement Waiver of Non-Jurisdictional Challenges: Yunis (723 F.2d 795), McCoy (477 F.2d 550).
Sentence Appeal Waiver Enforcement: Bushert (997 F.2d 1343), Howle (166 F.3d 1166), Bascomb (451 F.3d 1292), Read (118 F.4th 1317).
Supervised Release Conditions & Oral Pronouncement: Rodriguez, 75 F.4th 1231; Bates (213 F.3d 1336).

Legal Reasoning

1. Prohibition on Judicial Participation: Federal Rule 11(c)(1) forbids any judge from taking part in plea negotiations. A district judge’s comments urging a defendant to plead guilty or describing sentencing advantages (e.g., safety valve) may violate the rule. But when a first plea hearing ends in no plea, and a second hearing before a different judge follows a voluntary written plea agreement, Eleventh Circuit precedent holds that the initial error does not taint the ultimate plea.

2. Plain-Error Review: When a defendant neither objects in district court nor reserves an issue, relief is available only for “plain error”: an unpreserved legal error that is obvious, affects substantial rights, and “seriously affect[s] the fairness, integrity, or public reputation of proceedings.” Windham could not show that, but for the first judge’s remarks, he would have gone to trial rather than pleading guilty a week later.

3. Plea Voluntariness and Safety Valve Information: Rule 11 requires courts to ensure pleas are uncoerced and that defendants understand charges, rights waived, direct consequences, and potential penalties. Here, the second plea colloquy and plea agreement together demonstrated a voluntary, knowing plea. Misinformation or loose language about possible safety valve eligibility did not prejudice Windham, who reiterated his guilt and desire to avoid trial, never conditioned his plea on safety valve relief, and later sought to withdraw without contesting voluntariness.

4. Suppression Waiver by Unconditional Plea: Challenges to nondispositive, non-jurisdictional rulings (such as denial of a suppression motion) are waived by an unconditional guilty plea. Since Windham did not enter a conditional plea preserving the suppression issue, he lost the right to challenge it on appeal.

5. Scope of Sentence Appeal Waivers: A knowing and voluntary sentence appeal waiver bars most post-conviction challenges, including constitutional arguments and contested legal questions. Windham explicitly waived his right to appeal any aspect of his sentence, including supervised release conditions. His claimed due-process violation—failure to orally pronounce discretionary conditions—falls squarely within the waiver. Read confirms that even a meritorious due-process claim on appeal is barred when covered by a valid waiver.

Impact

Reinforces that preliminary judicial remarks, even if improper, do not automatically invalidate a later plea if a full Rule 11 colloquy cures any defect and the plea is voluntary.
Affirms the high hurdle of plain-error review: defendants must show a reasonable probability of going to trial but for the error.
Clarifies that misinformation about safety valve does not automatically render a plea involuntary absent prejudice.
Emphasizes that unconditional guilty pleas waive pre-trial motion challenges unless preserved by conditional plea.
Strengthens the binding effect of sentence appeal waivers, including for due-process arguments about supervised-release conditions not orally pronounced.

Complex Concepts Simplified

Plain Error: An appellate doctrine requiring an obvious, uncorrected error that changed the outcome to justify reversal when the defendant failed to object below.
Rule 11 Colloquy: The in-court questioning of a defendant by a judge to ensure a guilty plea is voluntary, informed, and supported by facts.
Safety Valve: A Sentencing Guidelines mechanism allowing below-mandatory-minimum sentences if strict criteria are met, including truthfully debriefing authorities.
Conditional vs. Unconditional Plea: A conditional plea reserves specific appellate rights (e.g., suppression rulings), whereas an unconditional plea waives most non-jurisdictional issues.
Sentence Appeal Waiver: A contractual agreement in a plea to forgo appellate review of a sentence, enforceable if knowing and voluntary.
Supervised Release Conditions: Post-sentencing restrictions; if discretionary (beyond statutory requirements), they must be orally pronounced or risk due-process challenge.

Conclusion

United States v. Windham clarifies important procedural aspects of federal plea practice. First, improper judicial comments in a non-conclusive plea hearing can be cured by a subsequent, full Rule 11 colloquy before a different judge. Second, a defendant bears the heavy burden of showing plain error—an obvious error that changed the plea decision. Third, unconditional guilty pleas waive collateral challenges such as suppression motions. Finally, knowing and voluntary sentence appeal waivers remain powerful shields against direct appeal of sentencing issues, including due-process claims about supervised-release conditions. Together, these principles provide practitioners and lower courts with clear guidance on the boundaries of judicial participation, plea voluntariness, and enforceability of waivers in the federal system.