Justices poised to adopt exceptions to federal criminal defendants’ appellate waivers

The Supreme Court heard oral argument on Tuesday in Hunter v. United States about what exceptions exist to federal defendants’ waivers of their right to appeal. The justices seemed poised to endorse more exceptions than just the two the government endorsed – ones for ineffective assistance of counsel in entering into a plea agreement and for sentences above the statutory maximum. A number of justices also expressed misgivings about relying on contract law to define exceptions to appellate waivers, the framework that both Hunter and the government principally invoked, and a majority seemed likely to hold, at a minimum, that a defendant could escape from an appellate waiver when enforcing it would result in a “miscarriage of justice,” a standard that a number of federal courts of appeals have applied.

Hunter pleaded guilty to one fraud count stemming from his decade-long financial scheme causing losses of nearly a half million dollars. In exchange for his plea, the government dismissed nine fraud counts and secured his agreement to waive his right to direct appeal and collateral review, except for claims of ineffective assistance of counsel. Hunter did not seek to challenge on appeal his sentence of 51 months of imprisonment. Rather, he challenged a special condition of his supervised release that follows his prison sentence, requiring him to take medication that his healthcare provider prescribed for his depression and anxiety. The U.S. Court of Appeals for the 5th Circuit dismissed his appeal under his appellate waiver.

Applying contract law to appellate waivers

Over multiple decades, the court has in a number of cases looked 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.” But as the court’s use of the word “analogy” would suggest, the court has been flexible in applying contract law when construing the terms of plea agreements.

Nevertheless, the emphasis that the court has placed on contract law in this context, and the way in which federal courts of appeals have used contract law for construing appellate waivers in particular, made it understandable that both Hunter and the government framed their arguments about exceptions to appellate waivers in that manner.

Hunter’s counsel, Lisa Blatt, began her argument with a focus on contract law and highlighting the narrowness of the exception to appellate waivers that Hunter sought. “Contract defenses are narrow by design and rarely satisfied,” she noted and continued that many of the claims that appellate waivers seek to bar would be precluded under Hunter’s approach. “Appeal waivers will continue to bar the vast majority of alleged sentencing errors, guidelines miscalculations, insufficient explanations, or misbalancing under [18 U.S.C.] 3553(a).” But she argued that “contract defenses may be satisfied in the rare case of clear legal error and punishment unauthorized by statute or that violates the Constitution.”

None of the justices’ questions, however, allowed her to address in any detail how that standard applies in Hunter’s case. In a theme that a number of justices raised, Justice Elena Kagan stated, “You refer to contract defenses. Then you say or a miscarriage-of-justice exception. In the time you’ve been up there, you’ve said the question is whether [the error the defendant is raising is] outside the realm of plausibility. You’ve referred to constitutional violations.” The justice continued, “I mean, when is it that this would come into play in your view more specifically?” Blatt replied, in keeping with how both sides framed their briefs, “the easiest and the high-level rule statement is it’s subject to contract defenses.”

But Justice Samuel Alito echoed a sentiment that seemed to capture what other justices expressed. “I think you’ve got a strong argument on something like a miscarriage of justice or something that’s shockingly improper, something that would capture the examples that you started out with, where the … sentence is based on race or religion or something like that.” But he continued that if the court were to rely on contract law doctrines like a public-policy defense, “then I get nervous because public policy is very broad.”

At one point, Justice Neil Gorsuch, who raised questions about the validity of all appellate waivers, proposed a test that he attributed to the U.S. Court of Appeals for the 4th Circuit. Under that standard, an appellate waiver would be unenforceable based on violating “a fundamental constitutional or statutory right that was firmly established at the time of sentencing.” Blatt responded, “I like that.”

When the government, represented by Zoe Jacoby, began arguing, the justices sought to clarify whether the government was in fact arguing that a broad appellate waiver like Hunter’s would bar claims like the examples Blatt had cited, such as a sentence imposed because of a defendant’s race. Jacoby answered that the government’s “front-line position is that there should not be an exception for – for even egregious miscarriage of justice because the Petitioner has argued this case based in contract doctrine, and we don’t think there’s a basis in contract doctrine for that.” The government also clarified that it was arguing that the contract defenses failed categorically for appellate waivers, explaining why there would not be a case-by-case analysis for a sentence imposed by, for example, a racist judge. But it was clear that the justices broadly rejected that view.

Justice Kagan perhaps captured the approach a majority of justices may be leaning towards. She asked Jacoby, “Why would it not be sufficient to say miscarriage of justice on the assumption that everybody who’s going to be applying that standard knows it’s a high bar, has seen it before, has thought about it before?”

Justice Kagan also raised a possible source for the court to adopt such a miscarriage-of-justice exception – namely, the Supreme Court’s supervisory powers over lower federal courts. “[W]e don’t need to point to a statute to be able to create a rule that polices the judiciary,” she noted.

Because of the court’s focus on the breadth and source of an exception for appellate waivers, the court did not address in any detail how it thought Hunter’s specific claim would be analyzed under that rule or whether the court would even address that question, instead of remanding his case for the 5th Circuit to perform that analysis in the first instance. The court also addressed only briefly a second question presented by Hunter, which was whether the district court’s statement at the end of sentencing that Hunter has “a right to appeal” made the appellate waiver unenforceable. It seemed plain that the justices would not address that issue in a way that avoided resolving what exceptions exist for federal inmates’ appellate waivers.

The court is expected to decide this case, at the latest, by the end of June or early July.