Will Donald Trump Go to Jail for Violating Gag Order? What We Know

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Former President Donald Trump should face indefinite prison time for again breaking a judge's gagging order, a former federal prosecutor has told Newsweek.

On Monday, Trump used the social media site Truth Social to attack a number of key figures involved in his federal election subversion criminal case, just hours after Judge Tanya Chutkan reinstated a gag order. Trump has also been twice fined for breaking a separate gag order in the New York Attorney General's civil fraud trial against The Trump Organization.

Neama Rahmani, a former federal prosecutor and the current president of the West Coast Trial Lawyers legal group, told Newsweek the judges are not enforcing the gag orders strictly enough.

Trump rally
Donald Trump arrives for a campaign event at the Orpheum Theater on October 29, 2023 in Sioux City, Iowa. He is now under gagging orders in both a civil and criminal case taken against him.... Scott Olson/Getty Images

"Trump has clearly and repeatedly violated the gag orders in both the New York civil and Washington, D.C. federal cases, but that doesn't mean anything if a judge won't do something about it," Rahmani said. "Trump can have his bond revoked in the criminal case, or he can be held in contempt in either case. But so far, the judges overseeing Trump's trial have been all bark, and no bite."

Trump was fined a total of $15,000 for twice violating the New York gag order.

"Fines of $5,000 or $10,000 are a slap on the wrist and woefully insufficient to deter someone like Trump. Judges are understandably hesitant to jail a former president, but he is being treated differently than any other criminal defendant. The First Amendment isn't absolute, and Trump's statements are intentional and cross the line of protected speech," Rahmani said.

He contrasted the leniency shown to Trump with the case of Sam Bankman-Fried, whose bail was revoked in August for attempting to contact a witness. Bankman-Fried is on trial for alleged fraud at the now collapsed cryptocurrency firm he established.

If Judge Chutkan revoked Trump's bond, he might remain in prison until the completion of his trial, which is scheduled to begin next March.

Judge Chutkan's gag order was imposed in D.C. federal court after prosecutors raised concerns Trump could intimidate witnesses or encourage harm against prosecutors through his public comments. Under its terms, Trump may not target court personnel, potential witnesses, or special counsel Jack Smith and his staff in public statements.

In one post last Monday, Trump attacked Smith, who is prosecuting the case, and Chutkan. "The Obama-appointed federal judge in D.C., a TRUE TRUMP HATER, is incapable of giving me a fair trial," Trump wrote. "Her hatred of President DONALD J. TRUMP is so great that she has been diagnosed with a major, and incurable, case of TRUMP DERANGEMENT SYNDROME!"

In another post, he attacked his former attorney general and a potential witness, William Barr.

"I called Bill Barr Dumb, Weak, Slow Moving, Lethargic, Gutless, and Lazy, a RINO WHO COULDN'T DO THE JOB," Trump said.

Trump has repeatedly complained about the gag order, which was frozen for nine days when he appealed it before it was reinstated on Monday.

He has said in court that the order infringes on his right to free speech and limits his ability to discuss the case on the campaign trail.

Alina Habba, one of Donald Trump's lawyers, claimed the prospect of the former president being sent to jail is "not even something that we think about" because he hasn't committed a criminal offense.

Habba, the general counsel of the pro-Trump Save America PAC, made the remarks in an interview on Monday with Newsmax host Carl Higbie, who asked whether "they even possibly throw him in jail," in reference to the 2024 Republican presidential frontrunner.

Trump is facing four criminal cases related to claims he orchestrated the payment of hush money to a pornographic actress, mishandled classified documents and broke the law attempting to overturn the 2020 presidential election outcome both across the United States and in the state of Georgia specifically.

The ex-president pled not guilty to all of the charges, which he insists are politically motivated. Trump is also embroiled in a number of non-criminal cases, including a $250 million civil fraud trial resulting from a lawsuit brought by New York Attorney General Letitia James, in which he also denies any wrongdoing.

Newsweek has sought email comment from Trump's legal team.

About the writer

Sean O'Driscoll is a Newsweek Senior Crime and Courts Reporter based in Ireland. His focus is reporting on U.S. law. He has covered human rights and extremism extensively. Sean joined Newsweek in 2023 and previously worked for The Guardian, The New York Times, BBC, Vice and others from the Middle East. He specialized in human rights issues in the Arabian Gulf and conducted a three-month investigation into labor rights abuses for The New York Times. He was previously based in New York for 10 years. He is a graduate of Dublin City University and is a qualified New York attorney and Irish solicitor. You can get in touch with Sean by emailing s.odriscoll@newsweek.com. Languages: English and French.


Sean O'Driscoll is a Newsweek Senior Crime and Courts Reporter based in Ireland. His focus is reporting on U.S. law. ... Read more