The Supreme Court opened its annual term Monday, with the justices returning to the bench for the first time since issuing a string of weighty decisions at the start of the summer.

After Chief Justice John Roberts officially opened the 2023 term in the courtroom, the justices heard oral arguments in a criminal sentencing case with implications for thousands of nonviolent drug offenders that turns on a grammatical debate over the meaning of “and.”

It is one of more than 30 cases the high court has already agreed to hear this term, including disputes on major issues like gun rights, social media and the administrative state. Other cases are likely to be added to the court’s docket in the coming weeks.

Monday’s ritual made clear the justices are continuing their post-pandemic tendency of stretching the length of oral arguments. The argument was scheduled for just one hour, yet lasted nearly double that.

At stake in Monday’s case was which defendants are eligible for lesser sentences under the First Step Act, a major criminal justice reform bill signed into law by then-President Trump.

The law expanded safety valve relief, which instructs courts to disregard mandatory minimum sentences when a defendant meets certain criteria.

Mark Pulsifer, who pleaded guilty to one count of distributing at least 50 grams of methamphetamine, believes he qualifies. He appealed to the justices after a lower court disagreed.

To be eligible, a defendant cannot have “(A) more than 4 criminal history points, excluding any criminal history points resulting from a 1-point offense, as determined under the sentencing guidelines; (B) a prior 3-point offense, as determined under the sentencing guidelines; and (C) a prior 2-point violent offense, as determined under the sentencing guidelines.”

At issue is how to apply the word “and” in the provision.

The Justice Department argues that “and” means “or,” so defendants are ineligible if they fail any of the three subparts. 

“It joins together three independently disqualifying conditions by distributing the phrase ‘does not have.’ That’s the only interpretation that avoids rendering the first subparagraph entirely redundant,” Frederick Liu, arguing for the government, told the justices.

But Pulsifer, who only fails two conditions, contends that “and” means he must fail all three to be ineligible.

“Letting the government get to ‘or’ when Congress said ‘and’ would encourage Congress to be sloppy with the most basic English words, leaving square corners far behind, and in the criminal context, where fairness matters most. The Court should hold Congress to what it wrote,” Shay Dvoretzky, Pulsifer’s attorney, told the justices.

Conservative Justice Neil Gorsuch and several other justices seemed sympathetic to Dvoretzky’s argument, while others’ views were more opaque.

“I think it’s a very hard case, so I don’t mean to suggest that it’s clear,” conservative Justice Amy Coney Barrett said at one point.

Liberal Justice Elena Kagan, who at times seemed sympathetic to the government’s argument, proposed a hypothetical to Dvoretzky about a doctor who advises a patient receiving a medical test to not eat, drink and smoke.

Dvoretzky conceded that “and” would effectively mean “or” in that situation, but he said it was a different context.

Kagan also made a distinction between a phrase like “don’t drink and drive” and the one used in the First Step Act.

“There’s something that connects those two things so that we know that the harm comes from the relationship between the two, whereas, in this case, we know that the harm follows from any one of the things,” Kagan said.

A decision in the case, Pulsifer v. United States, is expected by next summer.