Justices to consider breadth of a federal defendant’s waiver of appeal

In Hunter v. United States, to be argued on Tuesday, March 3, the Supreme Court will address how broad federal defendants’ waivers of their right to appeal can be and the effect of a district court’s statement at sentencing that the defendant may appeal when he previously agreed to an appellate waiver.

Hunter’s plea bargain and sentencing

Munson Hunter committed financial fraud that spanned about a decade, causing losses to his victims of nearly a half million dollars. He used false identifications to open bank accounts in fake names, fraudulently obtained loans and credit cards, and funneled thousands of dollars into bank accounts he controlled.

Hunter ultimately pleaded guilty to one count of aiding and abetting wire fraud, and in exchange, the government dismissed nine other fraud counts. As part of the plea bargain, Hunter agreed to a broad waiver of his right to pursue a direct appeal and a habeas petition, except for claims of ineffective assistance of counsel.

At sentencing, the district court imposed a sentence of 51 months of imprisonment (below the advisory guideline range of 63 to 78 months) and a special condition of supervised release, to follow his prison sentence.

The supervised-release condition at issue in Hunter’s case before the Supreme Court relates to anxiety and depression that Hunter had suffered since he was approximately 10 years old. Because mental illness can impair a defendant’s rehabilitation and increase recidivism, a court may order under 18 U.S.C. § 3583(d) and Section 3563(b)(9) that a defendant “undergo available medical, psychiatric, or psychological treatment” as a condition of supervised release. Given that Hunter in the past had refused to take medication, the district court ordered him to participate in mental health treatment and take medication that his provider prescribed. But the court told Hunter that “[i]f there’s a dispute, you can address it to the probation officer,” and “[i]f the probation officer can’t resolve the dispute, you can address it to me.” Hunter objected to this condition of supervised release, but the court rejected his arguments.

At the end of Hunter’s sentencing hearing, the court said, “All right. You have a right to appeal. If you wish to appeal, [Hunter’s counsel] will continue to represent you.” During Hunter’s earlier plea hearing, the district court had reviewed Hunter’s appellate waiver with him, but the court did not recap or mention that appellate waiver when the court notified Hunter of his right to appeal at the end of sentencing. Under Federal Rule of Criminal Procedure 32(j)(1)(B), “[a]fter sentencing – regardless of the defendant’s plea – the court must advise the defendant of any right to appeal the sentence.” This advisement comes at the very beginning of the 14-day window for a defendant to file a timely notice of appeal.

Hunter timely appealed, arguing that the right to challenge an unconstitutional sentence cannot be waived. The U.S. Court of Appeals for the 5th Circuit rejected that argument and granted the government’s motion to dismiss the appeal because of the appellate waiver. The 5th Circuit also rejected that the district court’s statement that he had a right to appeal made the appellate waiver unenforceable.

Hunter now contends that the 5th Circuit erred in dismissing his appeal.

The arguments before the court

Hunter frames his arguments by contending that the 5th Circuit has adopted an incorrect rule that only two limits on an appellate waiver exist – one for claims of ineffective assistance of counsel and one for sentences above the statutory maximum. (Whether that is in fact an accurate description of 5th Circuit precedent was contested by the parties when Hunter sought Supreme Court review but has largely dropped out of the case.)

In arguing that these two categories do not exhaust the exceptions to appellate waivers, Hunter broadly contends that he should not be held to have waived a claim that he could not have reasonably expected at the time of his plea agreement and that there must be a safety valve for egregious errors.

The Supreme Court has often looked, with caveats, to contract law when interpreting plea agreements. “Although the analogy may not hold in all respects,” the court has said, “plea bargains are essentially contracts.” In addressing the enforceability of his appellate waiver, both Hunter and the government thus argue over four contract-law doctrines – public policy constraints, unconscionability, implied duties of good faith, and frustration of purpose.

Looking to public policy, when a contractual provision is deemed to be unenforceable on this ground, courts will typically rely on some provision of law that the contractual term is deemed to violate. Anticipating the point that Congress has not prohibited appellate waivers, Hunter points to contract-law authority that does not require contractual provisions to be flatly prohibited by law to be deemed against public policy. For its part, the government notes that not only has Congress declined to prohibit appellate waivers, but also that courts permit waivers of rights, even important constitutional rights for guilty pleas even without an appellate waiver, such as the right to a jury trial, the right to confront witnesses, and many others. As the Supreme Court has broadly stated, “[a] criminal defendant may knowingly and voluntarily waive many of the most fundamental protections afforded by the Constitution.”

As to unconscionability (or the idea that some contracts are so unjust that they should not be enforced), Hunter draws on contract law doctrine and analogizes it to the rule some federal courts of appeals apply in saying that an appellate waiver is unenforceable when it would result in a “miscarriage of justice.” In response, the government reviews contract-law doctrine governing procedural unconscionability, which addresses the process in which a contract was formed, and substantive unconscionability, which evaluates whether a provision would be unfair to enforce.

Procedural unconscionability should not apply, the government argues, given the circumstances in which appellate waivers are formed. Defendants have a right to counsel and have the terms of plea agreements reviewed in court with a judge ensuring that the agreement is knowing and voluntary. As to substantive unconscionability, the government invokes the benefits of plea agreements, which here included the dismissal of nine counts in exchange for a plea and appellate waiver. As the government points out, an unconscionability ruling would curtail defendants’ ability to bargain for such advantages.

Hunter next maintains that enforcing an appellate waiver in the circumstances of his case would violate the government’s duties to act in good faith because precluding him from seeking review of the medication provision would exceed his reasonable expectations about the scope of the appellate waiver. In response, the government contends that implied duties of good faith in contract law do not nullify the express terms of contracts, and Hunter cannot point to the district court’s purported bad faith given that the district court is not a party to the plea agreement.

Lastly, Hunter argues that contract law excuses performance if, after the contract is formed, intervening events frustrate a party’s principal purpose in forming the contract. Under his view, avoiding the medication order was a principal purpose he had in entering the plea agreement. In response, the government rejects, among other things, that the absence of a medication condition was a basic assumption on which the contract was made.

As a fallback argument, the government contends that Hunter’s challenge to the special condition of supervised release fails to meet a miscarriage-of-justice standard. Because Hunter brought his appeal immediately after sentencing, he has not begun serving a term of supervised release, and no doctor has prescribed a medication over his objection. Nor has any court ordered him to take a particular medication.

Courts have developed a fulsome body of law governing compulsory medication and compulsory medical care generally, both in institutional settings and on supervised release. That body of precedent is impossible to apply without the specifics of both a defendant’s current medical condition and the proposed treatment. Because of that, as Hunter has acknowledged, under 5th Circuit precedent, his claim is not ripe until he faces an order to take a specific medication. Hunter could then challenge such an order when it arose.

A key question for Hunter’s overall argument is how Rule 32(j)(1)(B) applies when a defendant has waived some, but not all, avenues to appeal. On Hunter’s view, the court erred in saying that he has a right to appeal given the appellate waiver. He asserts that when the government failed to object to the court’s statement at the end of sentencing, that should count as a waiver of the government’s right to assert the appellate waiver altogether. The government responds that the district court’s statement was accurate because Hunter could file an appeal and some avenues to appeal remain despite the appellate waiver. Finally, the government also disputes the appropriateness of the remedy Hunter seeks of being freed from his appellate waiver altogether.