Justices Mull Grammar In First Step Act Resentencing Case

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The U.S. Supreme Court grappled with grammar-heavy arguments Monday over whether lighter sentences under the First Step Act should apply to defendants who were sentenced before the 2018 law was enacted but later resentenced after their original sentences were thrown out.

Defendants can benefit from a sentencing relief provision under the FSA for offenses committed before the law was enacted "if a sentence for the offense has not been imposed as of such date of enactment," the statute reads.

The justices are now mulling whether an initial sentence that has been vacated still meets the definition of "imposed" within the context of the FSA. If vacating a sentence means that it is no longer "imposed," the defendant could be resentenced under the FSA's significantly reduced statutory penalties.

"Well, it's always fun to talk about grammar and usage," Justice Samuel Alito quipped during Monday's arguments, eliciting laughter in the courtroom. He went on to ponder whether "present-perfect tense sometimes suggests in context that the past event continues to have present effect."

"So why would the past event have relevance in this situation?" Justice Alito asked. "I could see it where ... the sentence was vacated because it was invalid. But I find it harder to understand why that would be relevant, why a present effect would ... be relevant when the sentence was never invalid?"

Both the government and the defendants — three men convicted in Texas of charges tied to bank robberies — in the consolidated cases before the high court agree that the FSA should apply to post-enactment resentencings.

The defendants have asked the Supreme Court to reverse a Fifth Circuit panel's ruling that they could not benefit from the FSA when they were each resentenced to more than 100 years in prison in 2022 through a practice known as "sentence stacking," a harsh penalty that the FSA scrapped. 

The court's forthcoming decision would directly affect about two dozen defendants, according to Masha G. Hansford of the U.S. Solicitor General's Office, who argued Monday on behalf of the government. But the ruling could have ramifications down the road for many other defendants who were sentenced before the FSA's enactment and are appealing their convictions and sentences. The government did not respond to a request for comment. 

"For the next 20 to 40 years, there could be additional people who might win their attacks on underlying convictions that led to super-long sentences," former federal prosecutor Mitchell Epner, a criminal defense attorney at Kudman Trachten Aloe Posner LLP who has been following the case, told Law360.

"If the Fifth Circuit rule stays in place, it would be fruitless for them to attack those convictions, because they can't get resentenced to terms that they could actually complete," he said.

Arguing Monday for the defendants, Michael B. Kimberly of McDermott Will & Emery LLP asserted that a vacated sentence should be "treated as though it never was imposed," adding that the "rules of statutory construction do not require the court to turn a blind eye to common sense."

Kimberly declined to comment after the hearing.

Justice Ketanji Brown Jackson noted during Monday's arguments that she was trying to "figure out why it makes sense to distinguish in the group of people who still have to be sentenced for this offense between those who previously had one and those who didn't."

"It seems to me that that's the key question that we need to really ferret out when we're trying to understand where the lines are being drawn in this statute," she said.

The Supreme Court appointed Dechert LLP partner Michael H. McGinley to argue in support of affirming the Fifth Circuit's ruling, which is in line with the Sixth Circuit's stance on the issue but splits with rulings from the Third, Seventh and Ninth circuits.

The "most natural, commonsense understanding of the statute's text read as a whole" shows that it does not apply to defendants who have been sentenced before the law was enacted, even if their sentences were later vacated, McGinley told the justices Monday.

"Indeed, Congress' use of the indefinite article 'a' captures any sentence that has been imposed before enactment, even those that are later vacated," he said.

McGinley told Law360 in an email after the hearing that it "was a great honor to be appointed by the Supreme Court to argue this case, and I look forward to the court's decision." He declined to comment further.

The high court's decision could come down to whether the justices lean toward "emphasizing language" versus "practical effect," said Tama Kudman, who heads the white collar practice at Kudman Trachten. She also is not involved in the case but has been following it closely.

"This is squarely in the heart of the debate between textualism and literalism," Kudman said. "And I think the court has shown itself to be more textualist than literalist."

The fact that the high court agreed to hear the case — over the government's objection — also could be telling.

While the government agreed with the defendants that the FSA applies to post-enactment resentencing, it asserted that the circuit split on the issue was insignificant. The government also noted that pending legislation might lead Congress to resolve any ambiguities in the law and its application.

"The only reason for the Supreme Court to pick this case out of thousands of cases it might choose to review is that it wants to reverse," Epner said. "If it didn't want to reverse, it would have left this case alone."

The consolidated cases are Hewitt v. United States, case number 23-1002, and Duffey et al. v. United States, case number 23-1150.

--Additional reporting by Katie Buehler and Elliot Weld. Editing by Alanna Weissman.


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