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Trump Hush Money
Judge Juan Merchan ruled last Tuesday that Donald Trump will have to pay $9,000 for gag order violations. Justin Lane/AP

Donald Trump Won’t Stop Posting. The Courts May Not Be Prepared for That.

First Amendment law isn’t as clear around gag orders. “Most people don’t try to piss off their judge,” one litigator said of the unprecedented nature of Trump’s conduct in trials.

Donald Trump’s day in court Thursday began the same way it began on Tuesday: with his lawyer appealing to the judge that the former president’s posts about some key witnesses were not in violation of the court’s gag order.

Prosecutors in the New York criminal hush money case highlighted four posts Trump made this week, two aimed at former lawyer Michael Cohen and two at media executive David Pecker, who testified in the case just last week.

Trump and Pecker have “no animosity,” Todd Blanche argued to the judge. Cohen, on the other hand, has been “inviting and almost daring” the ex-president to respond to his public remarks, he said, arguing that witnesses like Cohen and Stormy Daniels do not “need to be protected.”

It’s certainly not the first time Trump’s conduct in and outside the courtroom has eaten into trial time; Judge Juan Merchan ruled last Tuesday that Trump will have to pay $9,000 for gag order violations. Legal experts and litigators watching the case predict it won’t be the last either.

In short, Trump, known for saying whatever he wants, appears incapable of silencing himself, and that reality is putting the courts in uncharted territory. Attorneys say the judges handling his cases will be breaking new ground as they attempt to stick to procedure in his trials.

“Merchan is operating in this area where First Amendment law is not as well defined as it is in most circumstances,” said Ken White, a First Amendment litigator at Brown White & Osborn LLP. “There is relatively little law on gag orders in trials because most people don’t try to piss off their judge.”

Trump was barred from making statements in public or online about any of the witnesses, counsel or jurors in connection to the hush money case. Earlier this week, prosecutors alleged that he violated that order 10 times, including in posts on Truth Social. Merchan agreed on nine instances, levying the $1,000 fine per violation, as is the maximum monetary punishment under New York state law. By Thursday, Trump had posted about people relevant to the case an additional four times.

Merchan acknowledged in his ruling earlier this week that the fine would do little, though, to “punish the offender” and “compel respect for [the judicial system’s] mandates’” because Trump “can easily afford such a fine.”

“[The court] must therefore consider whether, in some instances, jail may be a necessary punishment,” Merchan wrote on Tuesday.

Attorneys told NOTUS that a case involving gag orders is already unusual. But having someone like Trump, who is inclined to violate them, brings the case to new territory where procedure is not well known.

“It’s complicated in this area. Appeals, bonds and gag orders and the like. They’re unusual, and [Trump] and his lawyers are testing every single thing they can test,” criminal defense lawyer J. Craig Williams said. “So, we’re digging deep into the annals of our Code of Civil Procedures and trying to figure out what happens next.”

Trump has been facing gag orders in many of his legal troubles postpresidency. He paid fines of more than $15,000 when he violated orders in the New York civil fraud case. He’s also subject to another gag order in the D.C. election interference trial, which one attorney says will become a model in handling a case of that circumstance.

“The D.C. Circuit opinion about the gag order in that case is now like one of the leading cases on gag orders around because, generally, it’s something that doesn’t get appealed, and you don’t get court rulings on it,” White said about a December ruling by the D.C. federal appeals court.

In that case, a separate three-judge panel decided unanimously to uphold presiding Judge Tanya Chutkan’s decision to impose a gag order to block speech about witnesses and court staff connected to it. While their ruling regarding Trump’s election interference case held that restricting any speech that “targets” witnesses is too broad, they specified that Trump cannot comment about their participation in the trial. It was the first appellate court to give extensive reasoning for limiting the former president’s speech.

“Mr. Trump is a former President and current candidate for the presidency, and there is a strong public interest in what he has to say,” Judge Patricia Millett wrote in the ruling. “But Mr. Trump is also an indicted criminal defendant, and he must stand trial in a courtroom under the same procedures that govern all other criminal defendants.”

The gag orders have continued rolling in.

“This is all going to continue to be a big problem for Trump, who is not used to the fact that the sanctity of a court proceeding can usurp the First Amendment under certain circumstances,” said Joe Patrice, a former litigator at Lankler Siffert & Wohl LLP. “The odds that he will walk out of the courtroom and create more trouble for himself are high.”

Meanwhile, as Blanche defends Trump against further fines, the former president is taking the opportunity to fundraise simultaneously. In a message sent to supporters, Trump says he’s “been FULLY GAGGED” and “stuck in court all day” rather than on the campaign trail.

On Truth Social Thursday morning, Trump continued to attack Merchan, the presiding judge in his New York criminal case.


Calen Razor is a NOTUS reporter and an Allbritton Journalism Institute fellow.