Trump Might ‘Wipe His Ass’ with the Next Judge’s Gag Order: Insiders

After Donald Trump was gagged by court order Tuesday, legal experts and confidants of the former president predicted it would happen again.

But next time, Trump isn’t expected to comply.

“The boss is probably gonna wipe his ass with it. And then who knows what happens?” said a Trump insider who, like three others quoted in this story by The Messenger, declined to speak on the record for fear of stoking the ire of either Trump, prosecutors or both.

Some in Trump’s orbit worry he’ll wind up in jail and damaged by his incarceration if he violates a judicial gag order. Others say the gag order – and even the threat of jail -- could be the best thing for him politically, viewing his legal fights as consubstantial with his campaign.

Nobody close to Trump expects him to be quietly gagged.

Until Tuesday, Trump experienced no judicial checks on his incendiary commentary on the presidential campaign trail or on his Truth Social media account as he attacked prosecutors, witnesses and judges in his various criminal and civil cases.

But after a New York judge Tuesday issued a gag order after Trump posted an inaccurate claim about a court clerk, it was clear to Trump’s campaign and legal team that a potential gag order also looms in the January 6 criminal case presided over by U.S. District Judge Tanya S. Chutkan, a nominee of former President Barack Obama’s.

“The Obama judge is going to make him a martyr,” said one longtime adviser. “The judge is going to say in the middle of a campaign ‘I’m going to tell you what you can’t say, and that you can’t defend yourself except in the limited way we allow you to in court’? The majority of Americans aren’t following this, but they know that isn’t fair, that this is draconian.”

Trump’s lawyers have come under fire from critics for telling Chutkan to just ignore the Department of Justice’s request for a gag order. But insiders say the attorneys are just executing Trump’s will. And, they say, he sees the court of public opinion and the court of law as essentially indistinguishable.

“A gag order would have the added effect of bolstering his public argument that this is not a prosecution, but a political persecution by his opponent’s administration,” longtime Trump adviser Roger Stone told The Messenger in June.

“I think he has to keep talking in order to make his case in the court of public opinion,” said Stone. Stone himself was gagged by a court in 2019 and convicted of witness tampering and lying to Congress in the Russia probe of Trump, who then commuted his sentence.

Trump has called the criminal cases against him “election interference” and told crowds that the Democratic and Democrat-appointed prosecutors are “not coming after me. They're coming after you — and I'm just standing in their way."

Trump’s critics have long maintained that he should have been gagged long ago for making public statements that threaten potential witnesses and poison the jury pool. They want Chutkan to gag him.

“Trump’s plan is (1) to gloat if he gets away with trashing witnesses in defiance of the judge’s orders and (2) to play victim and make the judge’s life a living hell if she imprisons him to enforce her mandate,” longtime Harvard legal scholar Laurence Tribe posted on X in August.

“She should call the coward’s bluff.”

But if that happens, what would happen to Trump?

“The Secret Service is never going to let the court put a former president and presidential candidate in jail, but I guess stranger things have happened,” said another longtime Trump adviser. “What are they going to do? Put him on house arrest? Make him wear an ankle monitor?”

There are less-swaggering Trump insiders, though, including those who believe that Trump can’t sustain a campaign if he’s fighting to stay out of jail or on house arrest because he can’t stop trash-talking on social media.

“Trump’s power is his voice and any real legal threat of taking that away is just a problem,” a fourth insider said.

Beyond the legal complications, the controversy served as a reminder to the campaign that Trump’s social media activity has long been viewed as a negative by a majority of the electorate, according to numerous polls.

After Trump was kicked off Twitter in the wake of the Jan. 6 riots, he founded his own Truth Social media company and has been posting extreme and incendiary content and commentary since and before he announced his presidential bid in November. He has only posted one time on X, the site formerly known as Twitter: a fundraising pitch for his mugshot.

Trump seems willing to keep talking, if his Sept. 15 post on Truth Social is any indication.

"So, I’m campaigning for President against an incompetent person who has WEAPONIZED the DOJ & FBI to go after his Political Opponent, & I am not allowed to COMMENT?" Trump wrote. "They Leak, Lie, & Sue, & they won’t allow me to SPEAK? How else would I explain that Jack Smith is DERANGED, or Crooked Joe is INCOMPETENT?"

Until Tuesday’s gag order and deleted post, Trump campaign insiders said Truth Social was a happy medium: it gave Trump an outlet to post his thoughts, but it didn’t have far enough reach to cause constant headaches the way his Twitter feed used to.