When Donald Trump appeared last week in a Washington, D.C., courtroom for his arraignment on federal election charges, the presiding judge gave the former president a few simple instructions for staying out of jail while he awaited trial.

Trump could not talk to potential witnesses about the case except through lawyers, Magistrate Judge Moxila Upadhyaya told him, and he could not commit a crime on the local, state, or federal level. Both are standard directives to defendants. But then Upadhyaya added a warning that seemed tailored a bit more specifically to the blustery politician standing before her: “I want to remind you,” the judge said, “it is a crime to intimidate a witness or retaliate against anyone for providing information about your case to the prosecution, or otherwise obstruct justice.”

When Upadhyaya asked Trump if he understood, he nodded. Fewer than 24 hours later, Trump appeared to flout that very warning—in its spirit if not its letter—by threatening his would-be foes in an all-caps post on Truth Social: “IF YOU GO AFTER ME, I’M COMING AFTER YOU!” Over the following week, he attacked a potential witness in the case, former Vice President Mike Pence (“delusional”); Special Counsel Jack Smith (“deranged”); and the federal judge assigned to oversee his case, Tanya Chutkan, an appointee of former President Barack Obama (Smith’s “number one draft pick,” in Trump’s words).

Trump’s screeds highlight a challenge that will now fall to Chutkan to confront: constraining a defendant who’s both a former president and a leading candidate to take the White House—and who seems bent on making a mockery of his legal process.

“She’s in a tight spot,” Barbara McQuade, a former U.S. attorney in Michigan, says of Chutkan. Conceivably, the judge could find Trump in contempt of court and toss him in jail for violating the terms of his pretrial release. But even though in theory Trump should be treated like any other defendant, former prosecutors told me that he was exceedingly unlikely to go to prison over his pretrial statements. And Trump probably knows it. (Whether Trump will go to prison if he is convicted is another hotly debated matter.)

[Read: The humiliation of Donald Trump]

“I’m sure she would be very reluctant to do that, in light of the fact that he’s running for president,” McQuade told me. “So I think as a result, he has a very long leash, and I think he will simply dare her to revoke [his freedom] by saying the most outrageous things he can.”

At a pretrial hearing today, Chutkan issued her first warnings to Trump’s lawyers about their client, according to reporting by Steven Portnoy of ABC News and Kyle Cheney of Politico. “Mr. Trump, like every American, has a First Amendment right to free speech,” she said. “But that right is not absolute.” She said Trump’s presidential candidacy would not factor into her decisions, and she rebuffed suggestions by a Trump lawyer, John Lauro, that the former president had a right to respond to his political opponents in the heat of a campaign. “He’s a criminal defendant,” she reminded him. “He’s going to have restrictions like every single other defendant.”

Chutkan said she would be scrutinizing Trump’s words carefully, and she concluded with what she called “a general word of caution”: “Even arguably ambiguous statements from parties or their counsel,” the judge said, “can threaten the process.” She added: “I will take whatever measures are necessary to safeguard the integrity of these proceedings.”

Chutkan had called the hearing to determine whether to bar Trump and his lawyers from publicly disclosing evidence provided to them by prosecutors—a standard part of the pretrial process. The evidence includes millions of pages of documents and transcribed witness interviews from a year-long investigation, and the government argued that Trump or his lawyers could undermine the process by making them public before the trial. Despite her warnings to Trump’s team, she sided with the defense’s request to narrow the restrictions on what they could disclose, and she did not add other constraints on what he could say about the case.

Yet the effect of Chutkan’s courtroom comments was to put Trump on notice. If he continues to flout judicial warnings, she could place a more formal gag order on him, the ex-prosecutors said. And if he ignores that directive, she would likely issue additional warnings before considering a criminal-contempt citation. A further escalation, McQuade said, would be to hold a hearing and order Trump to show cause for why he should not be held in contempt. “Maybe she gives him a warning, and she gives him another chance and another chance, but eventually, her biggest hammer” is to send him to jail.

Judges have sanctioned high-profile defendants in other cases recently. In 2019, the Trump ally Roger Stone was barred from posting on major social-media platforms after Judge Amy Berman Jackson ruled that he had violated a gag order she had issued. (Stone did honor this directive.) The Trump foe Michael Avenatti, who represented Stormy Daniels in her case against Trump and briefly considered challenging him for the presidency, was jailed shortly before his trial on extortion charges after prosecutors accused him of disregarding financial terms of his bail. “He was just scooped up and thrown into solitary,” one of his former lawyers, E. Danya Perry, told me. She said that Avenatti was thrown into the same jail cell that had held El Chapo, the Mexican drug lord. (Avenatti later claimed that his treatment was payback ordered by then–Attorney General Bill Barr; the prison warden said he was placed in solitary confinement because of “serious concerns” about his safety, and Barr has called Avenatti’s accusation “ridiculous.”)

Neither Stone nor Avenatti, however, is as high-profile as Trump, arguably the most famous federal defendant in American history. And Perry doubts that Chutkan would imprison him before a trial. Trump has ignored warnings from judges overseeing the various civil cases brought against him over the years and has never faced tangible consequences. “He has done it so many times and he has managed to skate so many times that he certainly is emboldened,” Perry said.

Indeed, Trump has also suggested he would ignore a gag order from Chutkan. “I will talk about it. I will. They’re not taking away my First Amendment rights,” Trump told a campaign rally in New Hampshire on Wednesday.

Trump’s political motives for vilifying his prosecutors and once again portraying himself as the victim of a witch hunt are obvious: He’s trying to rile up his Republican base. Trump also seems to be executing something of a legal strategy in his public statements about the trial. He’s called Washington, D.C., “a filthy and crime-ridden embarrassment,” possibly reasoning that these remarks will force the court to agree to his request to shift the trial to a venue with a friendlier population of potential jurors, such as West Virginia.

[David A. Graham: Trump is acting like he’s cornered]

That’s less likely to work, according to the former prosecutors I interviewed. “I’d be shocked to see that be successful,” Noah Bookbinder, a former federal prosecutor who heads the anti-corruption advocacy group Citizens for Responsibility and Ethics in Washington, told me. “It’s sort of like the old joke about the child who kills his mother and father and then asks for mercy because he’s an orphan. I just don’t see a court going for that.”

Trump’s attacks also present a problem for Smith, the special counsel. On one hand, prosecutors have a clear interest in ensuring that their witnesses do not feel intimidated; on the other, Smith could feel that trying to silence Trump would play into the former president’s victim narrative. Justice Department prosecutors alerted Chutkan to Trump’s “I’m coming after you” post in a court filing, and during today’s hearing they voiced concerns that if not restricted, Trump could disclose evidence to benefit his campaign. (A Trump spokesperson said the former president’s warning was “the definition of political speech,” and that it referred to “special interest groups and Super PACs” opposing his candidacy.) But Smith’s team did not ask Chutkan to fully gag Trump or even admonish him. “You see the prosecutors being very, very restrained,” Bookbinder said. “With a lot of defendants who were bad-mouthing the prosecutor and witnesses, they would have immediately gone in and asked for an order for the defendant to stop doing that.”

Bookbinder described the citation of Trump’s post as “a brushback pitch” by the government, a signal that they are watching the former president’s public statements closely. But like Chutkan, Smith might be reluctant to push the matter very far. Fighting with Trump over a gag order could distract from where the government wants to focus the case—on Trump’s alleged crimes—and it could indulge his desire to drag out the trial, Bookbinder noted. But the special counsel has to weigh those concerns against the possibility that an out-of-control defendant could jeopardize the safety of prosecutors and witnesses. “My strong suspicion is that Jack Smith doesn’t want to go there,” Bookbinder said. “I think at some point he may have little choice.”

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