“Can make his life pretty miserable”: Trump faces “increasingly unpleasant” contempt punishments

Former President Donald Trump faces thousands of dollars in fines and a potential stay in jail if he continues to violate his gag order in his New York criminal case – but legal experts expect the businessman to keep risking the fines as he campaigns as the victim of a vast witch-hunt, and they say flaws in New York contempt laws and the wording of Trump’s gag order could help him fight any potential jail time.

On Tuesday, New York Judge Juan Merchan found Trump in "criminal contempt for willfully disobeying a lawful mandate of this Court" and ordered Trump to pay a total of $9,000 in fines.

The former president is fighting 34 felony charges of falsifying business records. Manhattan District Attorney Alvin Bragg alleges that Trump concealed payments made in a scheme to kill stories about his extramarital affairs before and after the 2016 election. Trump’s former special counsel Michael Cohen pleaded guilty in federal court to campaign finance violations for his role in those payments, which federal prosecutors said were to influence the election.

Under the gag order in the New York, Trump is directed to refrain from:

• “Making or directions others to make public statements about known or reasonably foreseeable witnesses concerning their potential participation in the investigation or in this criminal proceeding;”
• “Making or directing others to make public statements” about counsel other than the District Attorney, as well as counsel, court and DA staff and their family members – if he does so with the intent to, or knowledge that the statements would, materially interfere with “counsel or staff’s work in this criminal case.”

The gag order has a broader ban when it comes to jurors, prohibiting him from making “public statements about any prospective juror or any juror in this criminal proceeding.”

Criminal contempt in New York is punishable by a $1,000 fine or up to 30 days in jail – or both. 

Trump can appeal the $9,000 fine – and Gregory Germain, a law professor at Syracuse University, expects he will do so.

“It’s not earth-shattering, considering his wealth, it’s a relatively small amount of money,” Germain said.  “The bigger issue is, you know, what happens next? He's trying to control the proceeding. And the judge is trying to control the proceeding.

“I just don't see him shutting up,” Germain said. “And so he's going to keep pushing the issue. And the question is what does the judge do about it?”

In the Tuesday order, Judge Merchan pointed out that New York’s Judiciary Law doesn’t give him the “authority to craft an appropriate punishment when a $1,000 fine will not achieve the intended purpose.”

Namely – “where the contemnor can easily afford such a fine.”

Judge Merchan has said he’s open to the idea of jail time. 

“Because this court is now cloaked with such discretion, it must therefore consider whether in some instances, jail may be a necessary punishment,” Merchan wrote.

Trump wouldn’t be the first presidential candidate to run for office from behind bars. And the Secret Service has reportedly planned for Trump's potential imprisonment, according to ABC News. 

NYU Law emeritus professor Stephen Gillers said that jail time could be as short as an hour – potentially, a one-hour incarceration period on the morning of a trial day at the courthouse jail. 

“Merchan has a series of escalating incarceration options that will become increasingly unpleasant if Trump continues to violate the gag order,” Gillers said.

“The court holds over cards and can make his life pretty miserable for the duration of the trial through escalating contempt citations and jail time,” he added. “Now, he may see that as a sign of victimization that will endear him to his supporters. But he'll have to pay the price of the escalating jail time.”

But Germain said such a move would likely be risky, cause a lengthy legal fight and jeopardize the ongoing trial. 

“Push may come to shove, and the courts are going to have to make a decision what to do,” Germain said. “And I think the judge should try real hard not to put them in jail, because that would be crossing a line that the judicial system can't really handle.”

He added: “In the underlying case, I think it would be extraordinary to sentence a first time offender on a Class II non-violent felony to jail. I mean, it just isn't done.”

The gag order does provide Trump leeway when it comes to political attacks: the order said it “in no way prevents Defendant from responding to alleged political attacks.”

Trump has argued that he made the Truth Social posts at issue in Tuesday's order in response to political attacks.

Germain said he thinks it's unlikely that Trump will now “flagrantly violate the order" by naming jurors, for example.

"At the same time, I think he with some justification, feels that the order with respect to witnesses who are out on the talk show circuit lambasting him, that he should be able to respond to them," Germain said. "And it is kind of hard to explain why the court issued the order in a unilateral way saying he cannot criticize the witnesses, but they can criticize him.”

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Judge Merchan in his order said it’s possible that one of Trump's posts was a response to witness, and former Trump lawyer, Michael Cohen’s early April posts about Trump’s presidential run and potential pardons.  But for the other nine violations of the gag order, Judge Merchan said Trump can’t avoid the gag order by posing that argument. 

Those social media posts include seven instances where Trump re-posted other people’s content and shared them with his audience.

Gillers said it’s “easy” to argue such re-posts violate the gag order. 

“Given the fact that Trump's tweets and re-tweets reach a massively broader audience than the original tweet says that the court needs to be able to contain and restrict retweets because they can do as much damage as the original by the criminal defendant,” Gillers said.

However, Santa Clara University School of Law professor Eric Goldman – who also is co-director of the High Tech Law Institute – says it’s an open question whether Trump is legally protected when he shares third-party comments online. 

“It is possible that what he did in this circumstance was actually legally permitted,” Goldman said. “As much as that pains me to say it.”

In a blog post, Goldman cited cases involving Section 230 of the Communications Act of 1934, which says: “no user of an inactive computer service shall be treated as the publisher or speaker of any information provided by another information content provider.” 

He said it’s unclear whether Section 230 – which Trump has demanded be repealed – could apply to a court gag order. And Trump’s team hasn’t raised Section 230 as a defense in this case, though a court recently held that Section 230 protected Trump and Eric Trump’s tweets in a defamation case launched by a Dominion Voting employee.

“It's so frustrating to me because we all know what Trump's doing, but the law might nevertheless permit that, in this particular circumstance and in that particular way he did it,” Goldman said. “And Trump is a master at finding those soft spots of figuring out where there are gaps in the laws and then using them to his advantage.”

Germain said he also has concerns about the wording of the gag order itself.

It’s not Trump’s first gag order – in December, the U.S. Court of Appeals for the D.C. district narrowed the gag order in the federal case alleging he conspired to overturn the 2020 presidential election.

Judge Merchan’s gag order is highly similar to that appellate order:

• “...it prohibits all parties and their counsel from making or directing others to make public statements about known or reasonably foreseeable witnesses concerning their potential participation in the investigation or in this criminal proceeding.”
• “...it prohibits all parties and their counsel from making or directing others to make public statements about” counsel, court and counsel staff and their family members “with the intent to materially interfere with, or to cause others to materially interfere with, counsel’s or staff’s work in this criminal case, or with the knowledge that such interference is highly likely to result.”

Germain called the “potential participation” wording “weird.”

“That leaves him open to argue that he isn't talking about witnesses’ participation in the case, he's talking about their character, their credibility, or whatever,” Germain said.

“If he said this person shouldn't be a witness at the hearing, I guess that would concern their participation in the case,” Germain said. “But if he's not talking about their participation in the case, he's talking about them generally. I think there's an argument that it doesn't violate the language.”

Germain added: “I don't know how you could convict someone of a crime for doing something that doesn't clearly violate that language.”

“You know, it's not a perfect order,” he said. “There are very, very strong free speech, constitutional issues at stake, when you gag a political candidate in the middle of an election, a leading political candidate for president in the election.”

Another potential legal strategy for Trump's team: pointing to holes in New York's criminal and civil contempt laws.

Germain said unlike states like California that regularly update their statutory laws, New York’s contempt laws are “very restrictive” and old.

New York has a criminal statute on contempt in criminal law – and a separate Judiciary Law contempt provision that Germain said lacks typical protections for criminal defendants.

“It's really an amalgam of civil and criminal contempt,” German said. “And since it's not really criminal, they don't have to give a defendant all the normal criminal protections like a right to a jury trial.”

Germain said courts more frequently handle direct contempt cases – when a criminal defendant may spit in a judge’s face and wind up in jail overnight, for example. 

He says many of those cases never wind up in written appellate decisions. 

Germain said Trump's conduct fits into the bucket of indirect contempt. He said outside of New York, defendants in indirect contempt cases often receive more criminal protections.

“I think that's an area where the New York law is vulnerable to a constitutional challenge,” Germain said. “That in an indirect contempt, you don't have a right to a jury trial under this Judiciary Law provision. And the judge who's mad at you for not following the order is the one that has control over deciding whether you're guilty or not, instead of having a jury.”

He added: “Maybe if they send Trump to jail and the Supreme Court rules that it's unconstitutional, they'll then have to clean it up. I don't know. You know, it takes a crisis sometimes to get these laws modernized.”

Following Judge Merchan's order, Trump took down the specified social media posts just before the judge’s Tuesday 2:15 p.m. EDT deadline.

That same day, Trump used his social media platform to claim that the judge is rigging the election by taking away his constitutional right to free speech.

"Attacking judges is an integral part of his strategy and has been for many years," Goldman said. "It allows him to control the narrative and the outcome."

Whether courts will weigh in on Trump's tweets about judges is unclear.

“Trump will continue to experiment with a variety of different messages and tests where the judge’s limits really are," Goldman said. "And each time Trump does so we should acknowledge that's a financially advantageous movement, as part of his campaign coffers benefit with each time he claims the process is rigged.”