Enforcing Appeal Waivers Absent Government Breach: Government May Characterize Offense Conduct and Argue § 3553(a) Factors Within a Stipulated Guidelines Range

Case: United States v. Handler (2d Cir., Summary Order)
Court: United States Court of Appeals for the Second Circuit
Panel: Circuit Judges Denny Chin and Myrna Pérez (decided by a two-judge panel pursuant to IOP E(b))
Disposition: Appeal dismissed pursuant to appellate waiver; no breach of plea agreement by the government.
Note: This is a nonprecedential Summary Order (see Fed. R. App. P. 32.1; 2d Cir. Local Rule 32.1.1). It does not have precedential effect but offers practical guidance.

Introduction

In this sentencing appeal, Defendant-Appellant Martin Handler challenged the government’s sentencing advocacy as a breach of his plea agreement, seeking vacatur and resentencing before a different judge. The Second Circuit dismissed the appeal because Handler had agreed to a broad appellate waiver covering sentences “within or below” a stipulated Guidelines range of 51–63 months, and the court found no breach that would defeat the waiver.

The case arises from a multi-defendant prosecution involving misuse of federal funds tied to the U.S. Department of Health and Human Services (HHS). Handler pleaded guilty to conspiracy to defraud HHS (18 U.S.C. § 371), misapplication of federal funds (18 U.S.C. § 666), and tax evasion (26 U.S.C. § 7201), and received a 58-month sentence—within the stipulated range. His central appellate claim was that the government’s characterizations of his conduct (e.g., that he “stole” or “embezzled” federal funds) and references to additional facts (e.g., a “bag of cash” incident) contradicted the plea’s stipulations and thus breached the agreement.

The appeal presented two key issues:

• Whether the government’s sentencing advocacy—particularly its characterization of the offense and references to facts not spelled out in the plea—breached the plea agreement.
• Whether any breach, if established, would render the appellate waiver unenforceable.

Summary of the Opinion

The Second Circuit dismissed the appeal, holding that:

• The appellate waiver is enforceable because the government did not breach the plea agreement.
• The plea agreement expressly allowed both parties to:
  • Seek a sentence outside the stipulated Guidelines range based on 18 U.S.C. § 3553(a); and
  • Make “any arguments” regarding where within the stipulated range the defendant should be sentenced and “any facts relevant to sentencing.”
• The government’s characterizations of Handler’s conduct (including terms like “defraud,” “stole,” or “embezzled”) did not contradict any Guidelines stipulation (such as a stipulation to no economic loss for Guidelines purposes) because the agreement did not restrict § 3553(a) advocacy or offense characterization.
• The government’s mention of an alleged “bag of cash” kickback was in direct response to the district court’s restitution inquiry and fell within the agreement’s allowance to present “any facts relevant to sentencing.” The district court also clarified that the incident was material only to restitution, not to the sentence length.

Because no breach occurred, the appellate waiver barred Handler’s appeal from his within-range 58-month sentence.

Analysis

Precedents Cited and Their Role

• United States v. Brumer, 528 F.3d 157 (2d Cir. 2008) and United States v. Griffin, 510 F.3d 354 (2d Cir. 2007): The court reaffirmed that plea agreements are reviewed de novo and interpreted under ordinary principles of contract law. This frames the inquiry: start with the agreement’s text to determine the parties’ rights and limits at sentencing.
• United States v. Burden, 860 F.3d 45 (2d Cir. 2017): Establishes that appellate waivers are presumptively enforceable but may be set aside if the government breaches the plea agreement. The breach inquiry is thus dispositive of the waiver’s enforceability. Applying Burden, the panel analyzed whether the government’s statements crossed contractual boundaries; finding no breach, it enforced the waiver.
• Murphy v. Institute of International Education, 32 F.4th 146 (2d Cir. 2022): Although a civil contract case, Murphy underscores a core contract-law tenet: “We start with the text of the agreement,” which is “the most important consideration” in discerning the parties’ intent. The panel relied on this principle to give effect to the plea’s explicit clauses permitting broad § 3553(a) advocacy and factual presentations at sentencing.

Legal Reasoning

The court’s reasoning turns on the precise terms of the plea agreement and the distinction between Guidelines calculations and § 3553(a) sentencing advocacy:

1. Contractual text controls. The plea agreement did two critical things:
   • It set a Stipulated Guidelines Range (51–63 months) and prohibited either party from seeking unlisted Guidelines “departures or adjustments.”
   • But it simultaneously preserved broad § 3553(a) advocacy, explicitly allowing either party to seek a sentence outside the stipulated range based on § 3553(a), to argue for a particular sentence “within” the range, and to present “any facts relevant to sentencing” (subject to any proffer-agreement limits not at issue here).
   This architecture forecloses the claim that the government’s high-end recommendation or offense characterizations breached the agreement. The text affirmatively authorized those actions.
2. Guidelines stipulations vs. § 3553(a) characterizations. Handler argued that the government’s use of terms like “stole” or “embezzled” and its assertion that HHS was “defrauded” contradicted a Guidelines stipulation that HHS suffered no economic loss. The panel rejected this, emphasizing that:
   • The “no loss” stipulation is a Guidelines calculation point (affecting offense level), not a gag on § 3553(a) advocacy.
   • No clause barred the government from describing the offense’s nature or harm for § 3553(a) purposes, nor from urging the top of the stipulated range.
   • The agreement’s “any arguments” language expressly permitted such advocacy concerning both the § 3553(a) factors and placement within the range.
3. Responding to the court’s restitution inquiries is permitted. The district court asked about restitution and third-party knowledge. The government referenced a “bag of cash” incident to address those inquiries. The plea expressly allowed the parties to present “any facts relevant to sentencing.” The panel found this squarely within the agreement and noted the district court’s clarification that the incident was not material to the custodial sentence, only to restitution.
4. Appellate waiver enforced. Because there was no breach, the appellate waiver remained effective. Handler’s sentence (58 months) was within the stipulated range, and his waiver foreclosed a direct appeal. Result: dismissal.

Impact and Practical Implications

While nonprecedential, this order provides clear practical guidance for federal sentencing and plea drafting in the Second Circuit:

• Broad § 3553(a) rights mean broad advocacy latitude. If a plea preserves the parties’ rights to argue under § 3553(a) and to present “any facts relevant to sentencing,” courts will permit robust offense characterizations—even when the parties have stipulated to certain Guidelines calculations (e.g., zero loss). To limit such advocacy, the plea must expressly do so.
• “No departures/adjustments” does not equal “no variances.” A clause barring unlisted Guidelines departures or adjustments does not bar arguments for a variance under § 3553(a) unless the agreement clearly says so. Here, the plea explicitly permitted seeking a sentence outside the range based on § 3553(a), reinforcing that the two concepts are distinct.
• High-end recommendations within a stipulated range are typically safe. When the plea allows “any arguments” about where within the range to sentence, the government’s recommendation of the top of the range is ordinarily consistent with the agreement.
• Restitution-oriented facts are “relevant to sentencing.” When a court asks for restitution-related facts (e.g., third-party knowledge), the parties may present them, even if the facts are not recited in the plea stipulations. That does not, by itself, constitute a breach.
• Appeal waivers will be enforced absent a breach. Under Burden, appellate waivers are presumptively enforceable. Defendants seeking to avoid a waiver must demonstrate a breach. Where the plea’s text permits the advocacy in question, the waiver will bar an appeal from a within-range sentence.
• Plea drafting lessons.
  • Defense counsel: If the goal is to limit the government’s characterizations or use of certain facts, negotiate explicit constraints on § 3553(a) advocacy and on the scope of “facts relevant to sentencing,” or include a clause barring offense descriptions inconsistent with stipulated facts.
  • Prosecutors: To preserve flexibility, retain broad § 3553(a) language and the right to present “any facts relevant to sentencing,” and avoid clauses that convert Guidelines stipulations into global factual gag orders.

Complex Concepts Simplified

• Appellate waiver: A defendant’s agreement not to appeal a sentence that falls within specified parameters (here, within or below 51–63 months). Such waivers are generally enforceable unless the government breaches the plea agreement.
• Guidelines departures/adjustments vs. § 3553(a) variances:
  • Departures/adjustments are changes within the Guidelines framework (e.g., applying or not applying specific offense characteristics or departures authorized by the Guidelines manual).
  • Variances are sentences above or below the Guidelines range based on the statutory sentencing factors in 18 U.S.C. § 3553(a), which include the nature of the offense, deterrence, just punishment, and the history and characteristics of the defendant.
• “Loss” vs. “harm”: “Loss” is a term of art in the Guidelines affecting offense levels. A plea may stipulate zero “loss” for Guidelines purposes. That does not preclude the government from arguing that the offense caused “harm” or was serious for § 3553(a) purposes, unless the plea expressly forbids such characterization.
• “Any facts relevant to sentencing”: Language commonly used in plea agreements to allow both sides to present facts at sentencing (including for restitution) beyond those specifically set out in the agreement, absent restrictions such as a proffer agreement.
• Standard of review for plea agreements: De novo review, applying contract law principles. Courts look first and foremost to the written text to determine the parties’ intent.

Key Provisions of the Plea Agreement (as interpreted by the Court)

• Stipulated Guidelines Range: 51–63 months.
• No unagreed Guidelines departures/adjustments; no suggestion that the court or Probation consider such.
• Both sides may seek a sentence outside the stipulated range based on § 3553(a).
• Both sides may present any facts relevant to sentencing and make any arguments about:
  • Where within the stipulated range (or any range the court determines) to sentence; and
  • The § 3553(a) factors.
• Appeal waiver:
  • Defendant will not appeal a sentence within or below 51–63 months.
  • Government will not appeal a sentence within or above the range.

What the Court Did Not Decide

• The court did not need to resolve whether the government actually sought a sentence above the range; the record reflected a request for 63 months (the top of the range). In any event, the plea text permitted either party to seek a sentence outside the range based on § 3553(a).
• The court did not address any challenge to the underlying Guidelines calculations themselves; the dispute was about alleged breach and the scope of permitted advocacy.

Conclusion

The Second Circuit’s dismissal underscores a straightforward but powerful message: when a plea agreement preserves broad § 3553(a) advocacy and the right to present “any facts relevant to sentencing,” the government may characterize the offense conduct and argue for a high-end sentence within the stipulated range without breaching the agreement—even where the parties have stipulated to particular Guidelines calculations like zero loss. Absent a breach, appellate waivers remain enforceable and bar appeals from within-range sentences.

For practitioners, the decision highlights the primacy of the plea’s text: precise drafting is decisive. Defendants seeking to cabin sentencing advocacy must negotiate explicit constraints; prosecutors seeking sentencing flexibility should preserve expansive § 3553(a) and factual-presentation rights. Even as a nonprecedential summary order, United States v. Handler serves as a clear reminder that courts will enforce what the parties actually wrote.