A Justice Department request to impose a narrow gag order on former President Trump is raising a number of sticky issues for the court as it weighs how to address what prosecutors called “disparaging and inflammatory” remarks about nearly everyone involved in the Jan. 6 case.

The Justice Department argues Trump’s comments could taint the jury pool and intimidate witnesses who might be called to testify against him — threatening to damage the case with a series of remarks on social media and along the campaign trail.

But the request, if granted, raises First Amendment issues for the candidate and feeds into Trump’s long-running narrative that the Justice Department’s actions are designed to hamper his electoral prospects.

And the stakes are high for Trump, who has a predilection for making such remarks and ignoring the cautioning of staff, and who could face fines or even jail time for violating such an order.

“The devil will be in the detail. How do you frame an order that, on one hand, preserves the former president’s right to proclaim his innocence, including by making whatever outlandish — risible even — statements he wants, but drawing the line at intimidating statements?” said Jeff Robbins, a former state prosecutor now in private practice.

“The judge has to look down the road, not very far down the road, and have it in her mind, ‘OK, if he does this, I will have to do that.” 

In making its case, the Justice Department cited a number of comments from Trump, from late 2020 in attacking those who challenged his case that the election was stolen, to a series of remarks targeting witnesses, prosecutors, and the judge overseeing the Jan. 6 case.

“Since the indictment in this case, the defendant has spread disparaging and inflammatory public posts on Truth Social on a near-daily basis regarding the citizens of the District of Columbia, the Court, prosecutors, and prospective witnesses,” special counsel Jack Smith’s team wrote in the brief. 

“The defendant knows that when he publicly attacks individuals and institutions, he inspires others to perpetrate threats and harassment against his targets,” they wrote.

Still, Trump would be free to otherwise comment on the case, including proclaiming his innocence.

Laurie Levenson, a criminal law professor at Loyola Law School, said it’s a complex matter – requiring balancing between treating Trump like any other criminal defendant and making due First Amendment considerations. 

“The court cannot give the message that Donald Trump is not subject to the same legal standards. I think that’s very dangerous,” she said.

“Obviously, Donald Trump doesn’t see remarks the same way others do. And so I’m wondering if this sort of gives enough notice to him as to when he would be crossing the line… . He tends to just speak ad hoc in inflammatory phrases.” 

Trump immediately made clear he sees the request as an attack on his free speech rights and his campaign.

“Deranged Jack Smith, he’s the prosecutor, he’s a deranged person, wants to take away my rights under the First Amendment,” Trump said during a speech hours after DOJ filed its motion. “He wants to take away my right of speaking freely and openly.”

“Never forget our enemies want to stop us because we are the only ones that can stop them,” the former president continued. “They want to take away my freedom because I will never let them take away your freedom.”

Still, both Levenson and Robbins said Judge Tanya Chutkan will want to establish a record of setting clear guidelines for Trump and warnings of what statements could jeopardize the case.

“I am concerned [about] what’s going to cross the line into disparaging, inflammatory or intimidating. Now DOJ might say for example, ‘like the things that we filed in our motion.’ But you know, he’ll just find a new phrase, so it’s kind of going to be like Whack-a-Mole,” Levenson said of Trump, adding he may need to be warned before a formal order is issued.

“He’ll make an inflammatory statement, the judge will say, ‘warning, not okay.’ You’ll whack that mole; he’ll make another inflammatory statement … . Trying to get him to behave outside the courtroom in a way that we ask people to behave in a courtroom — it’s a long shot. ”

Robbins noted the issue is also more challenging for Chutkan as Trump has also filed an order asking her to recuse herself from the case.

“One of the things which is lurking in the background — and I’m sure his lawyers are mindful of it; he probably is as well — is this motion that she recuse herself. So he knows and his lawyers know the judge has to be careful that in entering any order or responding to this, she doesn’t do something which gives a motion to recuse legs,” he said. 

“He and his legal team know that she’s got to be — it’s a particular headache for her. It’s an additional headache for her deciding how to deal with this protective order issue.”

Renato Mariotti, a former federal prosecutor, said Chutkan has already previewed a way to address his speech and dodge the issue of a gag order, noting the judge has already warned she may have to bump up Trump’s March trial date if outside factors like his comments jeopardize the ability to carry out a fair trial in the courtroom.

“I actually think she’s more likely to do that because it’s not reviewable, really, on appeal, and she has wide discretion to do so. And I could see her moving up the trial date as a way of sending a message to Donald Trump rather than getting herself in this challenging situation where she’s trying to police his speech, which is always a tricky situation for a judge to be in,” Mariotti said last week during an appearance on MSNBC.

In some ways, the situation could be a win-win for Trump, who has already sought to politically capitalize on the gag order request, sending a fundraiser telling supporters, “If Joe Biden gets his way, this would be the LAST email I ever send you.”

Trump’s description of the order is not accurate, as he would still be able to discuss the case publicly. 

Ford O’Connell, a Florida-based Republican strategist, noted that Trump’s campaign has made a point of pushing the idea that there is a two-tiered system of justice in the country, and a gag order would likely only reinforce the belief among some that he is being unfairly targeted.

“They’ll absolutely rally around him even more than they already have, and he’s essentially the nominee at this point as is,” he said.

While Trump might launch a First Amendment challenge in court and on the campaign trail if an order is issued, Robbins noted the free speech protections are not absolute.

“Although the fact that he’s running for president is extraordinary, it doesn’t change the fundamentals of the precedent: that courts have the inherent authority to protect the fair administration of justice by preventing statements which are reasonably likely to interfere with jury selection, jury seating, or witnesses who are prepared to take the oath and tell the truth,” Robbins said.

Brett Samuels contributed.