• Trump’s legal team is battling prosecutors over a gag order issued this week in his hush-money case.
  • Legal experts told BI how the judge could respond to Trump’s continued challenges of the order.
  • On the extreme end, if Trump continues to push the limits, he could end up in jail, an expert said.

Trump is playing with fire with his social media posts these days.

As his legal team dukes it out with Manhattan prosecutors over the scope of a gag order issued this week in his hush-money case, the former president hasn’t slowed his virtual attacks on the judge overseeing the proceedings or stopped taking jabs at the judge’s daughter.

The continued remarks, two legal experts told Business Insider, could result in Trump being held in contempt of court — which means he could face additional charges, fines, or even jail time.

A gag order under review

Judge Juan Merchan on Tuesday issued the order barring Trump from making public comments about witnesses, court staff, and jurors in light of his previous "threatening, inflammatory, denigrating," remarks during the civil and criminal cases against him.

Trump made it less than 24 hours after the order was issued before making a post on Truth Social aimed at Judge Merchan and his daughter, Loren Merchan, who is president of the progressive political consulting firm Authentic Campaigns.

Judge Merchan, Trump wrote early on Wednesday, suffers "from an acute case of Trump Derangement Syndrome " and his daughter Loren, he added, "just posted a picture of me behind bars, her obvious goal," referring to a social media account apparently associated with the judge's daughter.

The account, which once belonged to Loren Merchan, had been deleted over a year ago and revived by someone else, but it is unclear who. A court spokesperson told The New York Times that the account's reactivation under an email address not affiliated with Loren Merchan was a "manipulation of an account she long ago abandoned."

In a series of back-and-forth letters to Judge Merchan on Thursday and Friday, prosecutors and Trump's legal team argued over whether the gag order "protects family members of the Court," or simply those listed in the order.

On Saturday, Trump continued his jabs at the Merchan family, posting a link to a New York Post article containing photos of the judge and his daughter. The article focused on how clients of Loren Merchan's company, Authentic Campaigns, used Trump's legal battles to fundraise.

While not illegal, some critics argue Loren Merchan's role in promoting progressive politics creates an appearance of a conflict of interest for Judge Merchan. Trump's legal team last year filed a motion urging Judge Merchan to recuse himself due to his daughter's work, per The Times. Still, the outlet reported the judge declined, citing a judicial ethics committee's findings that his impartiality could not "reasonably be questioned."

"This is a disgrace to our Legal System," Trump captioned the post. "Judge Merchan should be immediately sanctioned and recused, and this fake "case," only kept alive by the Highly Conflicted Judge, should be completely dismissed right away - THERE IS NO CASE, THERE IS NO CRIME."

Though he has repeatedly lambasted Judge Merchan's daughter for working with politicians who have used Trump's legal woes to fundraise, the former president also uses his court battles as a reason his supporters should donate money to him.

Reuters reported fundraising groups — including some associated with the Republican National Committee — have urged donors to fund Trump's legal fights directly and have spent tens of millions of dollars on his legal fees.

On Monday, Judge Merchan is expected to address the dispute over whether Trump's continued statements about Merchan or his daughter violate the gag order. He is also expected to notify Trump's legal team of possible sanctions should his inflammatory remarks online be determined to violate the order.

Todd Blanche, a lawyer for Trump in the case, did not immediately respond to a request for comment from Business Insider.

A 'win-win' for Trump either way

Neama Rahmani, a trial lawyer and former federal prosecutor, told Business Insider that, while it's unlikely Merchan will expand the gag order to include his daughter, having already allowed Trump to criticize himself and District Attorney Alvin Bragg, "seemingly because they're public figures," there are potential consequences the former president could face for his remarks — if Merchan is bold enough to enforce the gag order.

"The problem with the gag orders in Trump's previous civil trials is they had no teeth. The judges didn't enforce them, aside from imposing nominal fines," Rahmani said. Trump faced a $10,000 fine in October for violating the gag order in his New York civil fraud trial.

Rahmani continued: "It's too early to tell if Merchan will actually enforce his order and hold Trump in contempt if he violates it, but otherwise, it's not worth the paper it's written on."

Andrew Lieb, a litigation attorney and legal analyst, told Business Insider he expects a tighter gag order to be issued and, based on that clarified order, Trump might be held in criminal contempt if he violates it.

"Trump loves to play the game of pushing the envelope to show what he can get away with," Lieb said. "And he feels like it's win-win either way because on one hand, if they hit him with contempt, then he's a martyr, and on the other, if they let him keep doing what he's doing, then he shows that he can get away with anything. But if it were you or I, I would never be playing the games he's playing — he's playing with his freedom."

Being held in contempt of court is no small matter, Lieb noted, and the average defendant would have likely already been smacked with a charge or significant fine if they acted as Trump has been acting in court.

And while Trump is no average defendant, Lieb said continuing to target the judge or his daughter may prove to be too much for the court to tolerate, especially in light of escalating threats against judges associated with Trump's legal battles and their families.

"I think the next step is to make the order a clear, expressed, and unambiguous order of the court," Lieb told Business Insider. That means clarifying exactly who is protected by the gag order's restrictions. "The step after that is probably a fine, then after that probably either a much bigger fine or putting him in jail for a short period of time to see if he gets the hint. I could see the judge putting him in jail for lunch, to be honest with you, just to make the point."

Lieb added: "I think this is going to escalate. Trump may not lose a trial that isn't appealable before the election, but I think he's gonna go to jail for contempt at one of these points because he keeps pushing the envelope. And as they say, when you play with fire enough, you get burned."

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