Will Donald Trump Go to Jail if He Breaks Gag Order Again? What We Know

Donald Trump faces the very real prospect of becoming the first former president to be jailed if he violates his hush money trial gag order again, a legal expert has told Newsweek.

Andrew Warren, a state attorney for Florida's 13th Judicial Circuit, said the former president should take Judge Juan Merchan "at his word" about serving jail time if he continues to flout the ban on him speaking out about aspects of his trial.

Merchan, who is overseeing the falsifying business records trial in which Trump has pleaded not guilty to 34 charges, fined the former president $9,000 on Tuesday for contempt of court in relation to nine online comments about potential witnesses and others connected to the criminal case in New York.

In his written order, Merchan said that criminal contempt is punishable by a maximum fine of $1,000, and jail time of up to 30 days. The judge also warned Trump that the court will not tolerate "continued willful violations" of the gag order and he would consider "incarceratory punishment" for future violations.

Donald Trump in New York
Donald Trump after a day at Manhattan Criminal Court. Judge Juan Merchan fined the former president on Tuesday for defying a gag order and warned further violations could mean jail time. EDUARDO MUNOZ/POOL/AFP/Getty Images

Warren said that Merchan appeared to be serious about taking the unprecedented and hugely significant decision to jail a former U.S. president.

"We should take the judge at his word," Warren told Newsweek. "He said the court will not tolerate future willful violations of its orders, and he appears to mean it."

"Thousand-dollar fines may not suffice to scare a man who revels in breaking the rules, but a night in the clink just may."

The nine violations for which Trump was fined the maximum $1,000 each were in relation to Truth Social comments and reposts, as well as statements on his campaign website. Many of the comments targeted Trump's former lawyer Michael Cohen and adult film star Stormy Daniels, both key witnesses.

Prosecutors had alleged 10 violations, but Merchan ruled one Truth Social post was not in violation of the gag order as Trump's argument that it was in response to a political attack was "sufficient to give this Court pause" as to whether it met the threshold.

Warren suggested that while Merchan was "clearly displeased" with Trump's conduct, the fact he ruled one of the Truth Social posts was not a violation showed the judge's "objectivity even in the face of Trump's misconduct."

However, Kevin O'Brien, former assistant U.S. attorney, suggested that Trump will still continue to violate the gag order even with the threat of jail looming over him.

"Trump shouldn't test Merchan, but he will, inevitably, as the evidence at trial gets worse and worse for him," O'Brien told Newsweek.

"The question is will Merchan finally pull the trigger. I'm guessing he will not, partly because he wants the trial to stay on track and avoid side shows, partly because the precedent of jailing a former president and presidential contender weighs on him, and partly because of the heat he will take from sectors of the media and Trump supporters."

Trump's office has been contacted for comment via email.

The gag order permits Trump to speak out against Merchan and the case against him.

In a post on Truth Social, Trump claimed that Merchan has "taken away my Constitutional Right to FREE SPEECH" by imposing the gag order.

"I am the only Presidential Candidate in History to be GAGGED. This whole 'Trial' is RIGGED, and by taking away my FREEDOM OF SPEECH, THIS HIGHLY CONFLICTED JUDGE IS RIGGING THE PRESIDENTIAL OF 2024 ELECTION. ELECTION INTERFERENCE!!!" Trump wrote.

In his order, Merchan said he is "keenly aware of, and protective of" Trump's First Amendment rights as he seeks a return to the White House, which is why the gag order had some allowances.

"It's critically important that Defendant' legitimate free speech rights not be curtailed, that he be able to fully campaign for the office which he seeks and that he be able to respond and defend himself against political attacks," Merchan said.

Trump has pleaded not guilty to 34 felony counts of falsifying business records in relation to "hush money" he allegedly arranged for his former lawyer Cohen to pay Daniels, in the run-up to the 2016 election, to keep secret a rumored affair she had with Trump.

The money was listed in Trump's company records as "legal fees," which prosecutors suggest was part of an unlawful attempt to influence the outcome of the 2016 presidential race. Trump denies an affair with Daniels.

Update 05/02/2024, 9:52 a.m. ET: This article has been updated with comment from Kevin O'Brien.

Uncommon Knowledge

Newsweek is committed to challenging conventional wisdom and finding connections in the search for common ground.

Newsweek is committed to challenging conventional wisdom and finding connections in the search for common ground.

About the writer


Ewan Palmer is a Newsweek News Reporter based in London, U.K. His focus is reporting on US politics, domestic policy ... Read more

To read how Newsweek uses AI as a newsroom tool, Click here.
Newsweek cover
  • Newsweek magazine delivered to your door
  • Newsweek Voices: Diverse audio opinions
  • Enjoy ad-free browsing on Newsweek.com
  • Comment on articles
  • Newsweek app updates on-the-go
Newsweek cover
  • Newsweek Voices: Diverse audio opinions
  • Enjoy ad-free browsing on Newsweek.com
  • Comment on articles
  • Newsweek app updates on-the-go