Post-Esteras Clarification: Consecutive Revocation Terms May Rest on Breach of Trust; Appeal Waiver in Rule 11(c)(1)(C) Plea Forecloses Reasonableness Attack on a Within-Range Sentence

Introduction

In United States v. Charles Henry Milton, III, the Sixth Circuit, in an unpublished opinion, affirmed two intertwined district court rulings arising from a combined proceeding: (1) a 108-month sentence for new narcotics and firearms offenses to which the defendant pleaded guilty under a Rule 11(c)(1)(C) agreement, and (2) a revocation judgment imposing 24 months’ reimprisonment for violating supervised release from an earlier felon-in-possession case, ordered to run consecutively.

The appeal presented two principal issues. First, whether the district court’s decision to impose a consecutive 24-month term upon revocation was procedurally and substantively reasonable—particularly in light of the Supreme Court’s decision in Esteras v. United States, 145 S. Ct. 2031 (2025), which confirms that courts may not consider the retributive factors in § 3553(a)(2)(A) at revocation. Second, whether Milton could appeal the reasonableness of his 108-month sentence in the new drugs-and-guns case, notwithstanding his Rule 11(c)(1)(C) plea agreement containing an appellate waiver that capped his appellate rights at the top of an agreed 70–108 month range.

The court held that the revocation sentence was both procedurally sound and substantively reasonable because the district court grounded its decision in the breach-of-trust paradigm and the relevant § 3583(e) considerations, not in disallowed retribution; and that the plea-based appellate waiver foreclosed review of the reasonableness of the within-range 108-month sentence.

Summary of the Opinion

The panel (Moore, Bush, and Davis, JJ.; opinion by Davis, J.) consolidated Milton’s two appeals and affirmed across the board.

Supervised release revocation (Case No. 24-4066):
- Procedural reasonableness: Reviewed for plain error due to a nonspecific objection after sentencing. The district court adequately considered the statutorily permitted § 3553(a) factors incorporated by § 3583(e), Milton’s violation conduct and history, and the applicable policy statement recommending consecutive terms (U.S.S.G. § 7B1.3(f)). The court’s “respect for law” comments, in context, reflected sanctioning Milton’s breach of trust rather than impermissible retribution under Esteras.
- Substantive reasonableness: Reviewed for abuse of discretion. The 24-month term was within the operative guideline range because the statutory maximum displaced the higher advisory range (U.S.S.G. § 5G1.1(a)). A within-range sentence is presumptively reasonable; Milton did not rebut that presumption.
New case sentence and appellate waiver (Case No. 24-4067):
- The court enforced Milton’s appeal waiver, which reserved only the right to challenge a sentence exceeding the agreed 70–108 month range (or above a statutory maximum). Because the district court imposed 108 months—within the range—his reasonableness challenge was barred. The record established the waiver was knowing and voluntary under Rule 11(b)(1)(N).

Analysis

Precedents Cited and Their Influence

Holguin-Hernandez v. United States, 589 U.S. 169 (2020):
Reinforces that a defendant preserves a substantive reasonableness claim by advocating for a shorter sentence; no special post-sentence objection is needed. The Sixth Circuit applied abuse-of-discretion review to Milton’s substantive reasonableness argument accordingly.
United States v. Sherrill, 972 F.3d 752 (6th Cir. 2020); United States v. Coleman, 835 F.3d 606 (6th Cir. 2016); United States v. Bostic, 371 F.3d 865 (6th Cir. 2004):
Together, these decisions govern preservation of procedural challenges. A general objection lacks the specificity required when the district court asks for objections post-sentencing. Because Milton objected to “that imposition” without detail, plain-error review governed his procedural attack.
Esteras v. United States, 145 S. Ct. 2031 (2025):
Clarifies that § 3583(e) excludes § 3553(a)(2)(A)’s retributive considerations—“just punishment,” “seriousness of the offense,” and “respect for the law”—from revocation decisions. The Sixth Circuit held the district court did not transgress Esteras because its rationale centered on breach of trust, deterrence, public protection, and policy statements, not punishment for the violation conduct.
Johnson v. United States, 529 U.S. 694 (2000):
Postrevocation sanctions are part of the penalty for the initial offense, not punishment for new crimes. The court invoked this framework to explain that considering violation conduct to assess the severity of the breach of trust does not amount to punishing the violation conduct itself.
United States v. Morris, 71 F.4th 475 (6th Cir. 2023):
Confirms that sanctioning the “breach of trust” is a proper purpose of revocation sentencing. The panel emphasized that Esteras did not disturb this principle.
United States v. Johnson, 640 F.3d 195 (6th Cir. 2011); United States v. King, 914 F.3d 1021 (6th Cir. 2019):
District courts must consider the Sentencing Commission’s policy statements (notably U.S.S.G. § 7B1.3(f), recommending consecutive revocation terms), but need not cite them expressly if the record shows consideration. The panel found adequate consideration here.
United States v. Vonner, 516 F.3d 382 (6th Cir. 2008) (en banc); United States v. Bradley, 897 F.3d 779 (6th Cir. 2018):
A within-guidelines sentence carries a rebuttable presumption of substantive reasonableness—a “tall order” to overcome. The 24-month term fell within the operative range (after application of § 5G1.1(a)).
U.S.S.G. § 5G1.1(a) and United States v. Pizzino, 501 F. App’x 535, 536 n.1 (6th Cir. 2012):
When the guideline range exceeds a statutory maximum, the statutory maximum becomes the guideline sentence. The district court’s 24-month term was, therefore, “within” the guidelines for presumption purposes.
Appellate waiver cases: United States v. Milliron, 984 F.3d 1188 (6th Cir. 2021); United States v. Pitts, 997 F.3d 688 (6th Cir. 2021); United States v. Sharp, 442 F.3d 946 (6th Cir. 2006); United States v. Presley, 18 F.4th 899 (6th Cir. 2021); United States v. Russell, 26 F.4th 371 (6th Cir. 2022); United States v. Noble, 762 F.3d 509 (6th Cir. 2014):
These authorities frame how and when appeal waivers are enforced. Where the sentence falls within the agreed range and the Rule 11 colloquy establishes that the waiver was knowing and voluntary, the waiver is binding and forecloses appellate review. Failure to brief a challenge to the waiver’s validity waives the issue.

Legal Reasoning

1) Revocation sentence: Procedural reasonableness under plain-error review

The court first sorted preservation and standard of review. Because defense counsel offered only a general objection to “that imposition” when invited to lodge objections, Milton did not preserve a specific procedural claim. Plain-error review applied: he had to show an obvious error that affected substantial rights and the fairness or integrity of the proceedings.

The court then examined the record against the § 3583(e) factors, which incorporate only a subset of § 3553(a). The district court:

Addressed Milton’s history and characteristics, including repeated noncompliance during supervision, positive drug tests, and multiple chances previously extended by the court.
Weighed the need for deterrence and protection of the public, relying on the government’s account of ongoing drug trafficking and Milton’s refusal to abide by supervision conditions.
Considered the guideline and policy framework for revocation, recognizing that the Grade A violation and criminal history yielded 33–41 months but that the statutory maximum capped the term at 24 months, and that policy statements recommend a consecutive revocation term (U.S.S.G. § 7B1.3(f)).
Considered the parties’ mitigation and aggravation arguments, including defense counsel’s emphasis that Milton had only 23 days left on supervision, and the government’s position that a concurrent term would leave the violation “without consequence.”

Responding to Milton’s core claim—that the court improperly focused on the nature and circumstances of the new offenses rather than the original felon-in-possession case—the panel held the record did not support that contention. The court was aware of the original conviction, relied on the violation report listing it, and heard defense counsel’s reminder that Milton had served 63 months for it. The district court permissibly considered the violation conduct to assess the severity of the breach of trust. That is distinct from imposing “just punishment” for the violation conduct, which Esteras forbids.

Although phrases like “respect for the law” can signal retributive reasoning, the panel found that in context the district court’s remarks captured Milton’s repeated squandering of chances and the need to ensure a consequence for the breach—squarely within the breach-of-trust rationale. There was, accordingly, no clear or obvious error—and, in any event, Milton did not show a reasonable probability of a more favorable outcome absent the purported error.

2) Revocation sentence: Substantive reasonableness under abuse-of-discretion

The court then addressed the claim that stacking the full 24 months consecutively to 108 months was “excessive.” Because the statutory maximum supplanted the higher advisory range, the 24-month revocation term was “within the guidelines” and presumptively reasonable. The district court canvassed the relevant factors and policy statements and articulated a coherent rationale for a consecutive term. Milton’s desire for leniency did not overcome the presumption, particularly against the backdrop of repeated violations and prior leniency that proved ineffective. The court therefore rejected the substantive challenge.

3) New-case sentence: Enforcing the appellate waiver

The plea agreement, entered under Rule 11(c)(1)(C), fixed a 70–108 month range. It also contained an appeal waiver reserving review only for sentences exceeding the top of that range (or statutory maxima). The district court imposed 108 months—a sentence at the top but within the agreed range.

Milton did not challenge the waiver’s validity in his briefing, thereby waiving that argument. In any event, the Rule 11 colloquy and the written agreement confirmed a knowing and voluntary waiver: the court explained the waiver in open court, checked Milton’s understanding, and Milton initialed each page (including the waiver) and signed the agreement. Under Milliron and related cases, the waiver “binds and forecloses” appellate review of a reasonableness challenge to a within-range sentence. The panel therefore dismissed the attack on the 108-month sentence as barred by the waiver.

Impact

Post-Esteras revocation practice: The decision underscores that district courts may continue to ground revocation sentencing in the breach-of-trust framework, deterrence, public protection, treatment needs, and the advisory policy statements, so long as they avoid the retributive purposes of § 3553(a)(2)(A). References that might sound like retribution (“respect for the law”) will be tolerated if the record shows the court is using them as shorthand for breach-of-trust concerns rather than to mete out just deserts for the violation conduct.
Consecutive terms for revocation remain the default recommendation: U.S.S.G. § 7B1.3(f) continues to carry persuasive force in favor of consecutive revocation terms. Explicit citation is unnecessary if the record reflects consideration. Defense counsel seeking concurrency must develop concrete reasons tied to § 3583(e)’s factors to overcome this default recommendation.
Preservation matters: Bostic-specificity remains essential. A generic post-sentencing objection will shift procedural challenges to plain-error review—often fatal given the high prejudice showing required. Counsel should identify the precise procedural flaw (e.g., reliance on § 3553(a)(2)(A), failure to address a mitigation argument, failure to consider policy statements) when the court invites objections.
Statutory maximums and the presumption of reasonableness: When the advisory range exceeds the statutory maximum, the maximum becomes the guidelines sentence under § 5G1.1(a). That repositioning confers the within-guidelines presumption on the statutory maximum, making substantive challenges to a full 24-month revocation term especially difficult.
Appeal waivers in Rule 11(c)(1)(C) agreements are robust: Reasonableness challenges to sentences within an agreed range are typically foreclosed. Defendants hoping to retain meaningful appellate review should negotiate narrower waivers, preserve breach arguments, or identify exceptions (e.g., sentences based on constitutionally impermissible factors, government breach, or ineffective assistance claims).
Mitigation based on “time served on supervision” has limited traction: The panel affirmed a consecutive maximum term despite Milton having completed “35 of 36 months” of supervision, indicating that completion of time alone—particularly amid repeated violations—may not carry dispositive mitigatory weight.

Complex Concepts Simplified

Supervised release revocation vs. new prosecution: Revocation punishes the original offense through a sanction for breaching the court’s trust; it is not punishment for the new violation conduct (which may itself be prosecuted separately).
What Esteras changed—and didn’t: At revocation, courts cannot invoke § 3553(a)(2)(A)—“just punishment,” “seriousness,” “respect for the law”—as a basis for the sentence. But courts can still rely on deterrence, public protection, treatment needs, and breach-of-trust rationales.
Procedural vs. substantive reasonableness: Procedural reasonableness asks how the court reached the sentence (consideration of proper factors, explanation, and avoidance of prohibited factors). Substantive reasonableness asks whether the sentence length is too long or too short in light of the factors.
Consecutive vs. concurrent: A consecutive term is served after another sentence; a concurrent term runs at the same time. For revocation, the Sentencing Commission recommends consecutive terms (U.S.S.G. § 7B1.3(f)).
Grade A violation and the statutory cap: Serious violations (e.g., new drug trafficking felonies) are Grade A. Even if advisory ranges exceed 24 months, revocation terms for most supervised-release offenders are capped by statute—often at 24 months. Under § 5G1.1(a), that cap becomes the guideline sentence.
Plain error: When an issue isn’t properly preserved, the appellant must show an obvious error that likely changed the outcome and seriously affected the fairness or integrity of proceedings—a difficult standard.
Rule 11(c)(1)(C) agreements and appeal waivers: In a “C plea,” the parties agree to a specific sentence or range that binds the court once accepted. Appeal waivers that track the agreed range will usually block reasonableness appeals for within-range sentences, provided the waiver was explained and understood at the plea colloquy.

Conclusion

Although not precedential, United States v. Milton offers a clear, post-Esteras roadmap for revocation sentencing and appellate waiver enforcement in the Sixth Circuit. On revocation, district courts may still impose consecutive terms grounded in the defendant’s breach of trust, deterrence, and protection of the public, while steering clear of retributive aims. The court’s acceptance of § 7B1.3(f) as a persuasive default and its recognition that § 5G1.1(a) converts statutory maximums into guideline sentences together make a full 24-month consecutive revocation term difficult to overturn, particularly under plain-error or deferential review.

On the plea side, the opinion reinforces that a knowing and voluntary appeal waiver in a Rule 11(c)(1)(C) agreement will be enforced as written: a sentence at the top of an agreed range is still “within range” and therefore unreviewable for reasonableness. Defense counsel should preserve procedural objections with specificity and carefully negotiate any waiver to preserve room for appellate review where warranted.

The key takeaways are straightforward: breach-of-trust remains a permissible and potent organizing principle for revocation sentencing after Esteras; the advisory policy favoring consecutive terms persists; statutory maximums can become the operative guideline sentence; and well-documented appellate waivers will bar within-range reasonableness challenges. These guideposts will shape district court practice and appellate strategy in supervised release and plea-driven sentencing for the foreseeable future.

Selected Citations

Esteras v. United States, 145 S. Ct. 2031 (2025)
Johnson v. United States, 529 U.S. 694 (2000)
United States v. Morris, 71 F.4th 475 (6th Cir. 2023)
United States v. Johnson, 640 F.3d 195 (6th Cir. 2011)
United States v. King, 914 F.3d 1021 (6th Cir. 2019)
United States v. Vonner, 516 F.3d 382 (6th Cir. 2008)
United States v. Pizzino, 501 F. App’x 535 (6th Cir. 2012)
United States v. Milliron, 984 F.3d 1188 (6th Cir. 2021)
United States v. Pitts, 997 F.3d 688 (6th Cir. 2021)
United States v. Sharp, 442 F.3d 946 (6th Cir. 2006)
United States v. Sherrill, 972 F.3d 752 (6th Cir. 2020)
United States v. Coleman, 835 F.3d 606 (6th Cir. 2016)
United States v. Bostic, 371 F.3d 865 (6th Cir. 2004)
Holguin-Hernandez v. United States, 589 U.S. 169 (2020)
U.S.S.G. §§ 5G1.1(a), 7B1.3(f)