FORT PIERCE, Fla. — A federal prosecutor in the classified documents case of former President Donald Trump clashed with the judge Monday as the prosecutor requested to bar Trump from threatening comments about law enforcement agents involved in the investigation.

Special counsel Jack Smith’s team is seeking to make as a condition of Trump’s freedom pending trial a prohibition on remarks that could endanger agents participating in the case. Prosecutors say those restrictions are necessary after Trump falsely claimed last month that the FBI was prepared to kill him when it searched his Florida estate for classified documents two years ago.

But prosecutor David Harbach, a member of Smith’s team, encountered immediate pushback from U.S. District Judge Aileen Cannon, a Trump appointee, whose handling of the case has generated intense scrutiny.

The judge questioned Harbach about how she could fashion an order that did not run afoul of Trump’s First Amendment rights and whether prosecutors could prove a direct link between Trump’s claims and actions that might then follow.

“There still needs to be a correlation between the alleged, dangerous comments and the risk” to public safety, she said.

As he tried despite interruptions from Cannon to rattle off the rationales that he said existed for speech restrictions on Trump, a visibly exasperated Harbach noted acidly that “I’ve got one reason out so far.”

The comment drew a rebuke from Cannon, who said: “Mr. Harbach, I don’t appreciate your attitude.” She said that if he could not behave in a more professional manner, one of his colleagues could take over.

Harbach completed his arguments and apologized to the judge, saying he hadn’t meant to be unprofessional.

Defense lawyer Todd Blanche disputed the idea that Trump’s comments posed an imminent threat to anyone in law enforcement and said prosecutors’ request would have a “chilling” effect. Trump is the presumptive Republican presidential nominee and is set to debate President Joe Biden on Thursday.

Trump’s often-incendiary rhetoric has been limited by courts before.

It was not clear when Cannon might rule.

Trump faces dozens of felony charges accusing him of illegally hoarding top- secret records and obstructing the FBI’s efforts to get them back. Given the breadth of evidence, many legal experts have regarded the case as the most straightforward of the four prosecutions against Trump, who has pleaded not guilty.