The Supreme Court of the United States late Tuesday morning heard oral arguments in a case that was fundamentally about what happens when a federal judge errs–and what relief a criminal defendant is entitled to based on how that error is catalogued under the rules governing federal lawsuits.

In Kemp v. United States, the nine justices were asked to consider the appropriate section of the Federal Rules of Civil Procedure under which an appeal after sentencing should have been filed. One section, if applied, would foreclose against any relief for the inmate. Another section, if applied, would result in a chance for the petitioner to re-litigate his claim at the trial court level.

The petitioner, Dexter Earl Kemp was convicted in 2011 for drug and firearms offenses and sentenced to 35 years in federal prison. After one failed appeal, the government considered Kemp’s judgment final in 2014. He sued again in 2015 claiming ineffective assistance of counsel. His case was dismissed by a district court judge, who followed the advice of the government, for having missed a deadline. All parties now agree that Kemp did not actually miss the deadline.

In 2018, 21 months after the district court dismissed his ineffective assistance of counsel claims, Kemp sued again. After much procedural wrangling, the government admitted the legal error but still said his lawsuit should be dismissed because his claim was filed over a year after the decision that relied on the legal error.

According to the court, under Rule 60(b)(1), which allows relief for “mistake, inadvertence, surprise, or excusable neglect,” Kemp only had a year from the date when his conviction became final to file his appeal. The court reasoned that Kemp’s appeal was based on the trial court having made a “mistake,” and the time for mistake-based appeals had run out.

Kemp, on the other hand argues that the catchall Rule 60(b)(6) should apply. That rule allows relief from a judgment “for any reason that justifies relief” and permits movants to file “within a reasonable time.”

On appeal, a three-judge panel for the U.S. Court of Appeals for the 11th Circuit (which included Barack Obama-appointed Circuit Judge Jill Pryor, and Donald Trump-appointed Circuit Judges Andrew Brasher and Barbara Lagoa) ruled against Kemp. The nation’s high court took up the case in order to resolve a decades-old circuit split on what, exactly, constitutes a “mistake” under the federal rules.

Justice Clarence Thomas started off questioning by asking Kemp’s attorney Andrew Adler if he was was conceding that the “plain meaning” of the word “mistake” doesn’t help the petitioner here.

Adler replied that “plain meaning” can be difficult to ascertain but later did concede the point. Kemp’s actual argument, the attorney said, is that “mistake” cannot mean a judge’s mistake “in this context” based on the “the text, structure, and precedent” of the federal rules.

The heart of Kemp’s argument is based on the principle of noscitur a sociis, a canon of construction that stands for the idea that, as one circuit court explained in 2015, “a word is known by the company it keeps—to avoid ascribing to one word a meaning so broad that it is inconsistent with its accompanying words.”

Essentially, because 60(b)(1) also contains references to “inadvertence, surprise, or excusable neglect,” the word “mistake” doesn’t make sense when applied to federal judges due to the nature of their work.

Kemp’s petition explains:

Those words contemplate relief where some oversight or carelessness by the litigants—not the court—contributed to the judgment. After all, courts do not “inadvertently” enter judgments. Nor are they “surprised” by their own judgments. And the ordinary meaning of the word “neglect” in the phrase “excusable neglect” refers to “inadvertence, mistake, or carelessness” by litigants. … Read in context, “mistake” refers to oversights by litigants that led to the judgment, not to a court’s own legal errors.

“Our position is the only viable position here,” Adler told Thomas–after running though his client’s basic argument. “And our position reads the rules as a coherent whole.”

The court, however, appeared all-but wholly unpersuaded by Kemp’s interpretation–oftentimes rejecting the petitioner’s framework and using the case to discuss ancillary issues entirely.

Justice Amy Coney Barrett disputed the basic premise accepted by both the government and the petitioner–suggesting that maybe it was Kemp’s attorney who made the error and the judge just didn’t catch it.

“You have the difficulty of distinguishing between fact and law, and then you also have the difficulty in identifying whose error was it,” she said. “I mean, I think the government makes a good point, that it can be difficult to figure out if a legal error was by the litigant or by the court.”

“It could be categorized as the counsel’s error,” Barrett added later on–pressing the attorney on the issue. “It could be categorized as the court’s error.”

Adler countered by saying the source of an error doesn’t particularly matter if a court signs off on it.

“I don’t think that’s a difficult distinction when we’re talking about legal errors because the district court has an independent obligation to ascertain and apply the law in every case regardless of what the parties say,” he said. “And so, when there’s a legal error, the only question is, well, did the district court commit an error? It doesn’t matter what the parties say.”

Justice Brett Kavanaugh, directly referring back to Thomas’s questioning, suggested the Second Circuit’s view that 60(b)(1) offers based on a court’s legal error has long been “workable enough” and was based on a plain meaning of the word “mistake.”

“[I]t didn’t conduct a textual analysis,” Adler replied. “It didn’t conduct a structural analysis of the rule.”

Kavanaugh, in the end, sided with Kemp’s position insofar as the plain meaning interpretation creates “overlap” and “redundancies” but remained unconvinced that the Supreme Court can “solve all the problems that are going to be created no matter which interpretation we adopt.”

Justice Stephen Breyer was also mainly concerned with the difficulty of distinguishing between errors of fact and law.

“[L]ook, the judges do make mistakes,” the retiring justice said. “Give them a quick chance to do it, even if it’s one of law. Call it to their attention. Six of one, half dozen of the other because we have problems both ways.”

Justice Sonia Sotomayor outright told Adler that she believed “the rules are in harmony” but that the “more important question” here is that the “circuits are all over the place” in terms of how to apply the rules.

“Only the Fifth and Tenth go the government’s way with an obvious legal error,” she said. “As Justice Kavanaugh pointed out, the Second, Sixth, Seventh, and Eleventh call it any legal error. I’m really not sure what the difference means or why.”

In the end, Sotomayor repeatedly asked Adler how the court should rule if they decide to rule against him in order to avoid rewriting 60(b)(6) in a way that would disallow the use of the rule for courts to address subsequent changes in law.

“I don’t see how the Court can write that opinion without–without throwing the lower courts and litigants into complete chaos,” the attorney said.

Neither Justice Samuel Alito nor Justice Neil Gorsuch spoke during oral arguments. Chief Justice John Roberts asked one question of Adler about the history of the rule.

Justice Elena Kagan only spoke up to ask government attorney Benjamin Snyder one question about the “category of mistakes” the court should embrace if they ultimately decide in the government’s favor.

“[W]e would describe that test as whether the issue is one that the district court just overlooked in entering its original judgment or if instead it’s an issue that the district court considered and just resolved in a way that the movant disagrees with,” Snyder said, offering an extremely narrow way to cabin “mistake” under the rules.

On rebuttal, Adler tried to re-simplify the legal equation:

(B)(1) is about mistakes of fact made by a party or someone in the litigation process. You make a mistake about what the trial date is. You make a mistake about whether you had been served with process. You make a mistake about whether the lawyer agreed to represent you. And then a judgment gets entered against you. The only recourse you have there is to reopen the judgment based on this mistake of fact. You can’t appeal it. It’s a fundamentally different situation where the judgment itself contains a legal error…

So whichever way you slice it, (b)(1) doesn’t cover this case. This case is governed by (b)(6). Mr. Kemp must show extraordinary circumstances on remand to reopen an erroneous final judgment. And that’s a very high bar for a reason because it protects finality.

Mr. Kemp asks only that he be afforded the opportunity to make that showing on remand.

[image via Chip Somodevilla/Getty Images]

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