Trump’s Infamous Trolling Could Now Send Him to Jail

Legal experts have been warning for months that former President Donald Trump’s big mouth could land him in fresh legal trouble—including, possibly, jail. 

On Monday, Trump took a big, new step in that direction. 

A federal judge in Trump’s federal 2020 election-subversion case in Washington D.C. slapped the former president with a partial gag order, barring Trump from publicly attacking his prosecutors, members of the court and also potential witnesses over matters relating to the case. The ruling blunts one of Trump’s favorite weapons—personal attacks on law enforcement officials and political enemies. 

The order means that Trump has finally been formally gagged in a meaningful way—one that takes Trump’s personal legal jeopardy to a new level. Now, he has to watch what he says on his Truth Social account, in his rambling speeches at rallies, and in combative press interviews. Running his mouth, in the freewheeling style he’s practiced for years, could now get him into big trouble—including, potentially, pretrial detention. 

“He doesn’t get to use all the words,” Judge Tanya Chutkan said in a combative hearing with Trump’s attorneys in a Washington D.C. federal courthouse on Monday. “He cannot use words that could be considered threats or attempts to influence testimony.”  

Some types of Trumpian invective are still in play.

Judge Chutkan made it clear that Trump could still, for example, insult his own former Vice President Mike Pence in a general way. Trump is currently dominating the race to become the 2024 GOP nominee, a race in which Pence is also attempting his own come-from-behind bid. Judge Chutkan acknowledged that some amount of sparring between them would be considered politics as usual. But Trump must refrain from attacking Pence using insults or threats that pertain to this case, in which Pence is a key player and potential witness. 

The ruling goes far beyond a much more limited order imposed recently by the New York City judge overseeing a civil fraud trial against Trump and his company. In that case, Judge Arthur Engoron ordered all parties to refrain from making verbal attacks on court staff after Trump’s Truth Social account recirculated a post disparaging one of Judge Engoron’s clerks. 

On Monday, Judge Chutkan declared herself “deeply disturbed” by that incident. 

The big question is: If Trump does trample on this order, what happens next?

A violation would put the ball back in Judge Tanya Chutkan’s court. She’d have to decide exactly how to deal with it, and she’d have a lot of options. 

In theory, she could boot Trump completely off social media for the duration of the trial. She could slap him with hefty financial penalties. She could move the date of his trial forward—in a case where Trump has been using every trick in the book to try to delay the trial until after the 2024 election.  

If the violation is severe enough, and if she has the nerve, she could potentially order him detained through the end of his trial in Washington D.C., which is currently scheduled to kick off March 4. 

It’s common for judges to give defendants warnings and to attempt to gradually roll out increasingly escalating punishments before jailing an offender. 

Judge Chutkan acknowledged during the hearing Monday that calibrating her response to a potential violation would be tricky.  

Imprisoning a former commander in chief would be unprecedented—and doubly so in light of Trump’s dominant position in the GOP presidential primary. 

Chutkan wrestled openly with that dilemma in court, asking both prosecutor Molly Gaston and Trump defense attorney John Lauro what her next moves should be if Trump breaks the order. 

“There are realities we have to face because the defendant is a former president,” Judge Chutkan said. 

Gaston responded that she believed the court should impose the order first, and then turn to possible punishments later. Lauro said that he believed putting a gag order on a major party frontrunner during a presidential election would o deeply contradict Trump’s right to freedom of speech. 

Enforcing such a ruling “in the middle of a campaign is impossible,” Lauro said.  

“I can’t conceive of an order that would be lawful; obviously we would appeal it immediately,” Lauro said. “In my view there should not be an order under any circumstances.”

But when Lauro argued that the conditions of release that Chutkan had already put in place were “working,” the judge let loose a hearty laugh.  

“I cannot imagine any other case where a defendant is allowed to call the prosecution ‘deranged,’ a ‘thug’ or anything else,” Judge Chutkan said, citing recent examples of Trump’s attacks on Special Counsel Jack Smith. 

Lauro repeatedly invoked President Joe Biden’s name in arguing that the case against Trump is fundamentally political in nature, while engaging in heated sparring with Judge Chutkan over the course of the two-hour hearing. At one point, he exclaimed that the famous political satirist George Orwell, author of the dystopian novel 1984, “would have a field day” with the proceedings underway in the courthouse on Monday.  

Judge Chutkan responded, calmly, with a note of irony in her voice: “George Orwell would definitely have a field day….”