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In Judge Kaplan’s court, Trump plays with fire

A misbehaving defendant claims to want a showdown Monday with a judge who has a unique track record on contempt

Former president Donald Trump's lawyer Alina Habba cross-examines E. Jean Carroll on Thursday at a Manhattan federal court. (Jane Rosenberg/Reuters)
6 min

In the high-stakes world of presidential trials, there are no judges like Lewis A. Kaplan.

At 79, after decades on the bench, the senior judge is one of the most well-regarded legal minds in New York. And he has a unique history that makes Donald Trump’s courtroom behavior over the past week potentially dangerous for the former president of the United States.

Trump is on trial in a civil case as writer E. Jean Carroll seeks damages from Trump, who has been found liable for defaming her when he made disparaging remarks denying he sexually assaulted her decades ago in a department store.

Trump has claimed that he intends to testify in the case on Monday — which would probably produce a dramatic courtroom showdown. But it’s unclear whether Trump will really show up. For one thing, he has made similar claims in the past, then not appeared. For another, Tuesday is the New Hampshire primary, and Trump is again running for president.

If he does testify, legal experts said, his time on the witness stand could be something akin to a suicide mission.

Over the past week, Kaplan’s handling of the damages trial in Lower Manhattan shows how different a federal courtroom is from most other parts of public life — even state court, where Trump and his lawyers had more leeway to squabble with a judge overseeing a different civil trial in another New York courthouse over the past several months. Kaplan has not tolerated similar behavior, and Trump has railed on social media that the federal judge is “a totally biased and hostile person.”

The former president claimed that he only lost a previous lawsuit brought by Carroll over the sexual assault and a different set of defamatory comments because he didn’t appear in court personally. Kaplan oversaw that lawsuit, too.

See how Trump is is making his court appearances seem like campaign stops

In recent weeks, Trump has been attending more court hearings than he needs to, seemingly deciding that the best way to fight his legal critics — and win the GOP nomination — is to try to shout them down. He has spoken out of turn in the courtroom and denounced the proceedings.

Legal experts warn that if he does so on the witness stand in Kaplan’s courtroom, he could end up humiliated and threatened with contempt of court.

Robert Katzberg, a veteran New York white-collar criminal defense lawyer, said Kaplan is “the worst possible draw for Trump,” not because of any personal or political bias, but because of the type of judge he is.

“He’s really smart and takes no guff from either side. He expects lawyers to be professional and toe the line, and if they do not, holds them accountable,” said Katzberg, who is now consulting counsel for Holland & Knight.

“Even if you had the most pro-Trump judge in America overseeing the trial, Donald Trump should not testify. Multiply that by a million with Lewis Kaplan on the bench,” he said. “Given both his lack of any relevant facts as to the only issue remaining — the damages suffered by Ms. Carroll — and Donald Trump’s inability to control himself emotionally, he is begging not only to be debased before the jury, but contempt citations will be looming large.”

Kaplan’s history with contempt is unique among the federal judiciary. In 2019, Kaplan sought to persuade federal prosecutors to charge a lawyer, Steven Donziger, with criminal contempt of court after he refused to give access to his communications.

When prosecutors declined, the judge took the rare step of appointing a private law firm to prosecute Donziger. The attorney was ultimately convicted and served 45 days in jail after already having spent more than two years under house arrest.

In court last week, Kaplan dropped the hammer on Trump when the former president flouted the rules of courtroom behavior.

After being told that Trump, sitting at the defense table, was denigrating Carroll loudly enough for the nine-member jury to hear, Kaplan ordered him to cut it out.

“Mr. Trump, I hope I don’t have to consider excluding you from the trial,” the judge said, adding that Trump has a right to be in court, but “that right can be forfeited … if he is disruptive.”

Trump threw his hands up in an animated show of disapproval.

“I would love it! I would love it!” he said.

Kaplan said Trump appeared unable to control himself.

“You can’t, either!” the former president retorted.

Outside court, Trump has fired off a relentless barrage of social media posts about Carroll.

Inside the courtroom, Kaplan has chided Trump’s lead lawyer, Alina Habba, who has little trial experience, for not knowing proper procedures and rules.

One exchange, about a defunct New York restaurant, sounded more like a scene from a Marx Brothers movie than a “Law & Order” episode.

Habba asked Carroll whether she was a regular at a Manhattan restaurant called Elaine’s.

“Yes,” Carroll replied.

“It’s incredibly hard to get into, correct?” asked Habba.

“Not [hard]. You can get into Elaine’s,” she replied, at which point Kaplan jumped in to say: “Ms. Habba, it hasn’t existed for years, if I’m not mistaken. … That may be on account of its being closed.”

Kaplan is asserting more control over the proceedings in this trial than was seen in recent months in a nearby state courthouse, where trial judge Arthur Engoron was more permissive toward Trump and his defense team in a civil case involving allegations of business fraud.

In Engoron’s court, multiple lawyers for Trump raised objections simultaneously — something generally unheard of in federal court, which tends to be more staid and subdued.

Kaplan immediately shut down similar efforts last week.

“Let’s just get this clear for both sides right now,” he said Wednesday. “The first lawyer who says anything when a witness is on the stand says everything there is to be said for that side. This is not a tag-team lawyering.”

In addition to her legal role, Habba serves as a publicist for Trump. She is also a regular on the social scene at Mar-a-Lago, Trump’s Florida home and private club, and joined Trump’s entourage at a UFC event in Las Vegas in December.

At the Carroll trial, Habba has repeatedly incurred the wrath of Kaplan for, among other things, not knowing or quickly forgetting how to question a witness or refer to exhibits.

She complained to the judge about this treatment, and about the limitations imposed on her questioning of Carroll, to no avail.

When the judge halted her questions about tweets, Habba bristled and said, “I can’t ask about them? With all due respect …” The judge quickly cut her off.

“All due respect,” the judge replied, “means that when I issue a ruling, you say next question.”