For three decades, US District Judge Lewis Kaplan has tolerated little disorder in his court, whether terrorists, royalty or a president are on the docket

Long before Donald Trump’s current trial for defaming journalist E. Jean Carroll, tensions have boiled over between the former president and the judge presiding over the case.

Since Carroll first sued Trump in federal court in November 2019, Trump has made a slew of insults about senior U.S. District Judge Lewis Kaplan: “Radical Left,” “Trump hating,” a “terrible person,” “completely biased,” and recently, one of the “animals” lined up against him in the U.S. justice system.

After years of simmering antagonism, Trump on Thursday plans to take the witness stand just a few feet away from the Bill Clinton-appointed federal judge — and is widely expected to provoke him. Kaplan tightly constrained the bounds of Trump’s testimony, and the former president has a pattern of flouting court orders. Earlier this month, Trump did not wait for a different Manhattan judge’s permission to speak in court before launching into a five-minute tirade against a separate lawsuit that may end the former president’s New York business empire.

“What's happened here, sir, is a fraud on me,” Trump told Manhattan Supreme Court Justice Arthur Engoron on Jan. 11, 2024, later telling the judge that he had an “agenda.”

Trump delivered that jeremiad in state court, and now on federal turf, Trump has little room to maneuver — and faces a judge with little patience for defiance. Legal experts warn that the Republicans' 2024 presidential frontrunner who has built his whole White House campaign around his courtroom troubles could soon be facing fines, contempt, or worse if he repeats his performance.

“The one thing I can say with certainty is that Judge Kaplan is a judge who sets rules and expects all people in his courtroom to abide by them, and if they don’t, he enforces them,” former federal prosecutor Mimi Rocah, who practiced in the Southern District of New York for a decade and a half, told The Messenger.

Donald Trump and SDNY Judge Lewis Kaplan
Anna Moneymaker/Getty Images; United States Courts /YouTube

Before the trial began, Judge Kaplan ruled that a prior jury’s verdict ordering Trump to pay $5 million to Carroll in damages for sexual abuse and defamation settled the factual record. As a result, Trump and his attorneys can no longer tell her jurors that he did not rape Carroll in the dressing room of a Bergdorf Goodman in the mid-1990s. Trump is also barred from denying on the witness stand that he defamed Carroll by denigrating her and falsely disputing her accusations.

Trump is not currently under any court order blocking him from attacking Carroll on social media or the campaign trial — and the former president does so routinely, a fact that Carroll’s lawyers brought up to jurors last week during opening statements to support their arguments for a significant financial penalty.

“He sat in this courthouse this morning, and while he was sitting there, he posted more defamatory statements, more lies about Ms. Carroll and this case,” Carroll’s attorney Shawn Crowley told the nine-person jury. “By our last count, 22 posts, just today. Think about that. Think about that when you consider how much money it will take to get him to stop.”

But a federal witness stand isn’t a social media platform.

The judge’s three-decade docket: From global terrorists to world leaders

If he fulfills his vow to take the stand, Trump must stick to a narrow range of relevant testimony — or face potential consequences from Kaplan.

Appointed by President Clinton to the lifetime seat on the bench in 1994, Kaplan has steered some of the most significant and high-profile cases in one of the busiest districts of the entire federal judiciary, including ones putting him in conflict with powerful people around the world. In the wake of the 9/11 attacks on the World Trade Center, Kaplan presided over some of the biggest terrorism cases in the proverbial shadow of the Twin Towers, and he closed Osama bin Laden’s docket after SEAL Team Six in 2011 killed the al-Qaida mastermind. Kaplan also oversaw the case of Ahmed Ghailani, the first and only former Guantanamo Bay detainee to be tried in a civilian court.

Upholding U.S. civil liberties, Kaplan excluded evidence from the trial derived from Ghailani’s torture, and a federal jury convicted Ghailani of only one of 285 charges related to the 1998 U.S. embassy bombings in East Africa. The political blow-back from that near-acquittal likely thwarted an effort to prosecute accused 9/11 mastermind Khalid Sheikh Mohammed in New York, but the surprising force of Ghailani’s defense before the jury mattered little for the defendant. Come sentencing time, Kaplan put Ghailani away for life.

Since that time, some of the most storied cases in the Southern District of New York — sometimes called “The Mother Court” because of its status as the nation’s oldest federal district — had a habit of landing on Kaplan’s docket.

Jeffrey Epstein survivor Virginia Giuffre’s lawsuit against Prince Andrew went to Kaplan’s court, and the judge’s refusal to dismiss the royal’s case on immunity or other grounds preceded the confidential settlement (at a reported $16 million) that roiled Buckingham Palace right before Queen Elizabeth II’s 2022 Platinum Jubilee.

That wasn't the only case on Kaplan’s docket that rattled global relations.

For more than a decade, Kaplan presided over a lawsuit filed by Chevron seeking to discredit a $9.5 billion environmental fraud verdict in Ecuador. The case raised contentious questions about a U.S. judge’s ability to sit in judgment over a foreign ruling, but Kaplan ultimately found in favor of the major oil and gas corporation in 2014, declaring the Ecuadorean opinion invalid and uncollectible in the United States. Ecuador's then-president Rafael Correa denounced the verdict as "judicial imperialism," but the aftermath of the case also demonstrated how Kaplan responds to any perception of defiance against his court orders.

After the Ecuadoreans’ lead attorney Steven Donziger refused to turn over certain post-trial discovery, Kaplan referred contempt of court charges to the U.S. attorney’s office, which declined to prosecute. Undeterred, Kaplan then drafted criminal charges against Donziger himself, appointed private prosecutors from a law firm, and transferred the case to a colleague on the federal bench. That maneuver stunned some observers in the U.S. legal community, who noted the rarity of a judge-ordered, private prosecution.

The U.S. Supreme Court nonetheless declined to review the controversial contempt convictions of Donziger, who served a six-month misdemeanor sentence that demonstrated the lengths to which Kaplan would go to control his courtroom.

Disgraced cryptocurrency billionaire Sam Bankman-Fried learned a similar lesson when Kaplan revoked his bail before a trial. Though he has yet to be sentenced, Bankman-Fried’s convictions last November in that case will likely keep the 31-year old fraudster incarcerated for many years.

E. Jean Carroll arrives for her defamation trial against Former President Donald Trump at New York Federal Court on January 16, 2024 in New York City.

Trump warned of consequences

On his website Truth Social, the former president offered a shorter synopsis of Kaplan’s three-decade long career: “Trump Hating, Radical Left Judge.”

After being slapped with a $5 million verdict in Carroll’s favor, Trump criticized Kaplan as a “terrible person, completely biased” — and added a dig for the “partisan” jury. (One of the unanimous jurors in that case was a regular listener and enthusiast of far-right podcaster Tim Pool.) That acrimony had built up over the course of the first trial, which ran last year from April 25 through May 9. Trump never appeared in court, but he attacked the trial participants on social media so often that Kaplan appeared to cryptically warn about the consequences for tampering with justice.

“If I were in your shoes, I’d be having a conversation with your client,” Kaplan told Trump’s then-attorney Joe Tacopina last April, citing “some relevant United States statutes” that could come into play.

Early on in the second trial, Kaplan fired a different shot across the bow, warning that Trump’s right to attend the trial could be “forfeited if he is disruptive.”

"Mr. Trump, I hope I don’t have to consider excluding you from the trial,” Kaplan told the former president one week ago. “I understand you are probably very eager for me to do that.”

"I would love it. I would love it," Trump responded and waved his hands.

"I know you would because you just can’t control yourself in this circumstance," Kaplan responded.

"You can’t either," Trump responded.

Legal expert Mitchell Epner told The Messenger that he “cannot imagine” what Trump might testify about without violating a court order — and he expected Judge Kaplan to act “quickly and decisively” if the former president did so.

“Judge Kaplan does not suffer fools at all, let alone gladly,” Epner said. “I could easily see Judge Kaplan terminating Trump’s direct testimony and holding Trump in contempt. I think a significant monetary fine would be more likely than jail. I could also imagine Judge Kaplan barring Trump from presenting any other evidence.”

Originally expected to testify on Monday, Trump received a reprieve after his lead attorney Alina Habba and one of the jurors fell ill. Habba said that she was exposed to COVID-19 through her parents and experienced a fever but tested negative. A juror who reported feeling hot and nauseous before trial was told to go home and get tested. Kaplan then adjourned the trial for two days, allowing Trump to go to New Hampshire for the GOP primary.

Given an additional day off after a decisive (if narrower-than-expected) victory in the New Hampshire primary, Trump is supposed to appear in court before proceedings begin at 9:30 a.m. EST.

Ben Feuerherd also contributed to this report.

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Trump Relishes in Tormenting Judges — But at E. Jean Carroll Trial That May Be a Dangerous Game