Back in the 1990s, when he was a smaller public figure, Donald Trump used to tell a story about his brush with financial ruin. It is in his third memoir, Trump: The Art of the Comeback, which covers the period after his massively overleveraged real-estate and casino empire collapsed, leaving him buried in debt. One day, when Trump was at his lowest point, he was walking along Fifth Avenue, holding hands with his second wife, Marla Maples. Trump pointed to a panhandler who was rattling a cup of change. “Do you know who he is?” he asked Maples.
“He’s a beggar,” she replied. “He looks so sad!”
“You’re right,” Trump said. “He’s a beggar, but he’s worth around $900 million more than me.”
Whether it is true or apocryphal, the anecdote tells you a lot about his emotional relationship to money. Here was a man who still lived in an 11,000-square-foot Trump Tower penthouse, still owned his mansion at Mar-a-Lago, and still had a former beauty queen on his arm — and yet in his own estimation, he was worth less than zero. In a 2007 deposition in a libel case he brought against a journalist who dared to question whether he was really a billionaire, Trump testified that much of his wealth was tied to the value of his personal brand, which fluctuated with “attitudes and with feelings, even my own feelings.” His net worth is not just a number. It is an expression of his self-esteem, the radioactive core that makes him run.
Last Friday, a jury of nine New Yorkers struck Trump in his softest spot, awarding $83.3 million to E. Jean Carroll, a writer who sued him for defamation. In her closing argument, Carroll’s lead attorney, Roberta Kaplan, had explicitly told the jury the case was “about punishing Donald Trump for what he has done and for what he continues to do.” What he had done, according to a previous jury verdict, was sexually assault Carroll in a Fifth Avenue department store, right around the same time The Art of the Comeback was published. What he had continued to do — even through the trial itself — was to savage Carroll, the federal judge hearing the case, and the whole “broken and unfair” legal system. Kaplan asked the jury to come up with a seemingly impossible figure: a number large enough to change Trump’s behavior.
“While Donald Trump may not care about the law,” Kaplan said, “while he certainly doesn’t care about the truth, he does care about money.”
Trump does not have to pay anything to Carroll yet. The damages award is certain to be appealed, and he presumably will use every tool at his disposal to thwart collection. (Much of The Art of the Comeback is about his struggles with people to whom he owed money.) And it seems unlikely that the result of the trial — the first of several, both civil and criminal, that Trump could potentially go through this year — will do anything to dent his position in the all-but-over race for the Republican presidential nomination. Yet the verdict does matter. The enormous damages add to the legal and financial pressures that are bearing down on Trump, which will soon grow heavier. As soon as this week, New York state judge Arthur F. Engoron is likely to issue a decision in a civil-fraud case against the Trump Organization. Attorney General Letitia James has asked the judge to assess $370 million in penalties, to place the company under independent monitoring for a period of at least five years, and to ban Trump for life from the real-estate industry and any role in managing his or any other New York company.
“There is no longer Justice in America,” Trump posted on his platform Truth Social after the verdict on Friday. His complaints are a central component of his campaign message, but they are not merely for political show. If he doesn’t have another comeback in him, Trump is in very real danger of being forced to sell assets or even choose bankruptcy. In a deposition in the fraud case last year, Trump testified that his company had $400 million in cash. If his estimate is accurate, he could be facing that much, or more, in legal liabilities by the end of this week. And that is before he even gets to his criminal trials, which might start this spring and could possibly land him in prison.
As he does whenever he loses, Trump complained that the Carroll trial was rigged. In this case, he wasn’t completely wrong. But he is the one who built the trap and sprang it on himself.
How did a fairly everyday dispute — she accuses, he says it’s a lie — turn into an $83 million verdict? In a time of mostly unchecked slander, defamation lawsuits have become a popular way for people who have suffered harm on social media to seek redress, as well an alternative route to accountability for conduct that cannot be criminally prosecuted. Yet the scale of the damages in this particular trial was also the culmination of years of Trump’s self-sabotage.
The legal saga began in 2019, when Carroll published a book containing a nine-page passage making public her rape allegation against Trump. An excerpt was published as a cover story in New York. In it, Carroll frankly acknowledged her reasons for keeping the story to herself for 30 years. “Receiving death threats, being driven from my home, being dismissed, being dragged through the mud, and joining the sixteen women who’ve come forward with credible stories about how the man grabbed, badgered, belittled, mauled, molested, and assaulted them, only to see the man turn it around, deny, threaten, and attack them, never sounded like much fun. Also, I’m a coward.” Within hours, Trump issued the first in a series of attacks on Carroll’s credibility via a statement from the White House press office, implying that the author and New York were being paid by the Democrats and suggesting that “people should pay dearly for such false accusations.” (I had no involvement in soliciting, editing, or publishing the story.)
That November, Carroll filed a defamation lawsuit against Trump over his denials in New York state court. The suit was removed to federal court, and the Justice Department took up his defense on the grounds that Trump had been “acting within the scope of his office” when commenting on a news story. Carroll’s supporters howled in protest, but this was not a completely trivial argument. The line between denial and defamation can be fuzzy. Trump’s initial comments included such assertions as “I have no idea who this woman is,” “it is a totally false accusation,” “it’s an absolute disgrace that she’s allowed to do that,” and — inevitably — “she’s not my type.” Later on, he went way further in maligning Carroll’s character and truthfulness, but in the original lawsuit, Carroll cited only those first statements from the White House.
According to a longstanding Supreme Court precedent, presidents are considered immune from lawsuits for actions taken within the “outer perimeter” of their official duties. The Founding Fathers — who were continually fighting with one another via sympathetic newspapers — had written similar protections for members of Congress into the speech-and-debate clause of the Constitution. They recognized that officeholders have to be able to express their views freely without fear of legal action. The principle applies especially to modern day presidents, who are under constant scrutiny, and who are followed everywhere by members of the press. In 2021, Attorney General Merrick Garland declined to reverse the Justice Department’s previous legal position, telling a Senate hearing that there should “not be one rule for friends and another for foes.”
The whole Carroll matter might have disappeared down the memory hole if Trump had been able to control his temper. In 2022, a divided federal-appeals court panel in New York found that as president he had been covered by a federal law granting civil immunity to executive-branch employees and referred the case to another appeals court in Washington to consider the issue of whether he was speaking in an official capacity. But then Lewis A. Kaplan, the district court judge overseeing the case, issued a ruling that denied Trump a stay of discovery while the appeal was considered, forcing him to sit for a deposition with Carroll’s lawyers. Trump posted a furious statement on Truth Social, calling the lawsuit a “complete con job” and labeling Carroll as a fabulist. “She completely made up a story that I met her at the doors of this crowded New York City Department Store and, within minutes, ‘swooned’ her. It is a Hoax and a lie, just like all the other Hoaxes that have been played on me for the past seven years. And, while I am not supposed to say it, I will. This woman is not my type!”
Carroll’s attorneys promptly sued Trump, now a private citizen, for defamation a second time while adding a claim under a newly passed New York state law that waived the statute of limitations for civil suits involving claims of sexual assault. That case went to trial in May 2023.
Trump was not required to attend the trial, and he decided to stay away. He has since blamed his then-attorney, claiming he advised it was “beneath me.” Because it was a civil case, it was decided under a lower standard of proof than it would have had it been in a criminal sexual-assault trial. The jury found that it was more likely than not that Trump sexually assaulted Carroll and awarded her $5 million — a relatively paltry sum for Trump. (He has filed an appeal.) Judge Kaplan had suggested at one point that it “could prove unnecessary” to hold a second trial. But the day after the verdict, Trump went on a CNN town hall and called Carroll a “whack job” with a “fake story.” Roberta Kaplan — who is not related to the judge — then filed an amended complaint in the original case, asking for millions more in damages. And Garland’s DOJ reversed its position on Trump’s immunity, citing the verdict and his continued verbal abuse. His chance of winning his presidential immunity appeal vanished.
Thus Trump got a second trial — but not a retrial. Judge Kaplan issued a decision declaring that the verdict in the first case would also hold for the sequel. Trump would not be allowed to argue he was innocent of sexual assault, putting him at a gigantic disadvantage. He and his attorneys couldn’t hide their disgust in court. Trump was reprimanded by the judge for muttering epithets like “con job” and “witch hunt” during Carroll’s testimony. As the defendant, he could — and did — take the witness stand, but he was not allowed to say much. Kaplan also ruled against his efforts to undermine his accuser’s credibility by “relitigating his charges of fabrication,” or introducing evidence about her past relationships and donations that helped to fund her lawsuit. (It received support from liberal tech billionaire Reid Hoffman.)
On the first day of the trial, before jury selection began, Trump’s lead attorney, Alina Habba, complained that the judge’s rulings had “gotten rid of any ability to meaningfully defend ourselves and President Trump in this case.” Kaplan was unimpressed. Throughout the trial, he curtly cut off any attempt the Trump legal team made to relitigate or grandstand. At one point, Trump’s three-piece-suited campaign adviser, Boris Epshteyn, stood up and tried to address the judge as his “in-house counsel.” Kaplan told him: “Please have a seat.” The judge repeatedly admonished Habba for making procedural mistakes in introducing evidence and for continuing to argue points that he considered settled. (On Monday, Habba wrote a letter to the judge complaining of his “overtly hostile” attitude and questioning whether he had shown “preferential treatment” to the plaintiffs, citing a New York Post article that reported he had been a “mentor” to Roberta Kaplan earlier in her career. Habba noted that one of Carroll’s other attorneys, Shawn Crowley, also had served as his clerk.) By the time of final arguments, matters between Trump’s legal team and the judge had grown so tense that Kaplan was openly threatening Habba in court. She attempted at one point to go on talking after the judge had ruled against her an evidentiary motion.
“I’m sorry, your Honor,” Habba protested. “I have to make a record.”
“Ms. Habba,” he said, “you are on the verge of spending some time in the lockup. Now sit down.”
“Shocking,” Habba said.
Outside of court, though, there were no such restrictions on Trump, who continued to call Carroll a liar and used his platform to tell his fans a distorted version of events inside the courtroom. He fixated on Carroll’s admission on the stand that she had deleted emails that contained death threats. “She got rid of massive amounts of evidence,” he said at a press event on the second day of the trial. (How it would have benefited Carroll to delete evidence that would have helped her case he never explained.) When she testified that she now sleeps with a gun she inherited from her father next to her bed because she fears someone out there might try to kill her, Trump accused her of being a lawbreaker. “It wasn’t licensed, so I guess she’s got a difficult problem, and that’s going to be her problem.” He called the trial a “totally rigged deal” over a “made-up, fabricated story.”
These and other statements were swiftly introduced into evidence by Carroll’s lawyers, adding to their case for punitive damages. I had witnessed this dynamic before, at the December defamation trial of Rudy Giuliani, whose defiance outside the courtroom created a sort of defamation feedback loop. A jury in that case awarded $148 million to the plaintiffs, a pair of Georgia election workers whom Giuliani falsely accused of election fraud, even during the trial. Watching Trump’s similarly insolent behavior, I could almost hear the meter ticking up.
Trump’s trial strategy was so sure to backfire that you had to wonder whether, on some level, he was inviting the damage. “You can imagine a world where the worse the number, the easier it becomes for Trump to spin his own narrative outside of the courtroom,” said Meryl Conant Governski, one of the Willkie Farr & Gallagher attorneys who represented the plaintiffs in the Giuliani defamation case. “That is what I keep coming back to when I hear about these antics.”
Then again, maybe Trump just can’t help himself. His uncontrolled conduct in the courtroom would seem like a foreboding sign for his defense in his potential criminal trials, where his personal risks will be even higher and where he will be required to be present in court for the duration. The jury in the Carroll trial was supposed to be insulated from news coverage, but of course they all knew who Trump was, and they could read his attitude with their eyes.
On the first day of the trial, before selection took place, Judge Kaplan told the potential jurors about unusual steps he had taken to preserve their anonymity, “to protect all of you from any unwanted attention or harassment.” The seven men and two women were picked from a larger pool of several dozen. Trump was there at the defense table, sizing up the candidates with an upturned chin. I couldn’t tell if these people in their winter coats had been warned ahead of time about the nature of the case when they had arrived for jury duty. One of the candidates, a woman who later made it on the jury, looked at the person next to her and mouthed, “It’s Trump.” But most of them had the impassive look of New Yorkers in the presence of celebrity.
The nine who were selected offered only scant biographical details. Four of them said they were foreign born or spoke with accents. One man was a musician. Another was a respiratory therapist. Another was a retired New York City Transit track supervisor. Another was a newly married 26-year-old who said he was in property management and maintenance. The two female jurors were a schoolteacher from Germany and a publicist for a tech company.
Trump left the courthouse after jury selection in order to attend a campaign rally in New Hampshire, so he was not present for opening arguments. That meant that when Roberta Kaplan delivered her closing last Friday, it was his first time hearing her case against him.
“Typically when someone is held liable in court for spreading false and defamatory lies, they stop,” Kaplan said, referring to the first verdict. “We all have to follow the law. Donald Trump, however, acts as if these rules and laws just don’t apply to him.” Trump was sitting with his arms crossed, glaring, a picture of discontent. Kaplan used him as a sort of exhibit. “Donald Trump spent his entire trial continuing to engage in the very defamation that landed him here in the first place.” As she was saying this, Trump stood up from the defense table, turned on his heel, and walked out. “He continued to defame E. Jean Carroll, proudly and repeatedly.”
Trump was holed up in a court across the hall that the Secret Service was using as a holding room by the time Kaplan started to lay out her case for damages. The plaintiffs had called one expert, Northwestern University professor Ashlee Humphreys, who also testified in the Giuliani trial. Humphreys has developed a model for measuring reputational damage on social media, based on an estimate of the number of views each defamatory message received. She estimated that it would cost as much as $12 million for Carroll to hire social-media influencers to spread corrective messages with similar reach. The plaintiffs asked the jury to give Carroll that much in compensatory damages, plus an additional $12 million for emotional harm. Throughout the trial, Carroll’s attorneys had introduced evidence of the personal harassment she continued to receive from Trump’s followers. In their closing, they displayed a message she posted on X last Christmas Day reading: “Our earth needs care and love. Not war and hatred.”
“We also need fewer money grubbing whores who lie,” read one comment.
“No way Trump touch this mess,” read another.
When it came to punitive damages, Kaplan didn’t cite a figure, only what the jury already knew about his wealth. “Millions of dollars to Donald Trump is just a drop in the bucket,” she said.
Trump strolled back to the courtroom, his right hand balled in the pocket of his suit coat, for his team’s closing argument. A New Jersey lawyer who connected with Trump after she joined his Bedminster golf club, Habba has a sharp-edged, theatrical style that is well suited to Trump’s broader purpose of communicating his resentment toward the legal process to the voting public. It did not go over so well, though, in Lewis Kaplan’s federal courtroom. She opened by playing a video of a Trump press conference that the plaintiffs had introduced as evidence of malice.
“There is no one that can truly express the frustration of the last few years better than my client, the former president of the United States,” Habba said. “They’re right; that’s how he feels. Can you imagine a world where someone can accuse you of a terrible accusation and then you defend yourself, respond to reporters on the South Lawn as the sitting president, and you can’t speak?”
The plaintiffs objected, but Kaplan let Habba continue. She pushed her luck.
“He has said the same thing over and over again, and do you know why he has not wavered? Because it’s the truth.”
“Objection,” Roberta Kaplan said.
“The jury will disregard that assertion,” the judge ruled. “It has been conclusively determined.”
“He’s right,” Habba went on. “A jury made a decision. A jury.”
Habba forged on. “Ms. Carroll cannot prove causation,” she said, her voice rising and elongating the syllables for emphasis. She argued that Carroll had brought the online abuse upon herself by publishing the story, fully knowing the reaction it would inspire. “President Trump has no more control over the thoughts and feelings of social-media users than he does the weather,” Habba said. “He does not condone them. He did not direct them. All he did was tell his truth.”
Habba questioned whether Carroll was really terrorized. “She’s enjoying this,” she said, pointing out that Carroll’s social-media following had grown and she was now friendly with Trump-hating celebrities. “She made an allegation in the most public forum by design, an allegation that my client has continuously and consistently stated his position. It is an American right.”
“Objection,” Roberta Kaplan said.
“Members of the jury,” the judge repeated. “It is conclusively determined who is telling the truth about the event, that is to say, whether Mr. Trump sexually attacked or assaulted Ms. Carroll or not. It’s established. You must accept that.”
“It is established by a jury,” Habba said. “You’re right, your Honor.”
“It is established,” Judge Kaplan thundered, “and you will not quarrel with me.”
In the plaintiff’s rebuttal, Shawn Crowley said Habba’s central argument was yet more proof that Trump was unrepentant. “Ladies and gentlemen, his truth was a lie,” she said. “That may be how Donald Trump lives his life, telling a truth that is a lie, but it is not how it works under the law. The sexual assault happened, and Donald Trump had no right to say otherwise.” She challenged the argument that Carroll should have known what she was in for. “You know what that sounds like. You have heard it before. She asked for it.”
Crowley went on, addressing the jury directly. “I would ask you to think about what Donald Trump wants you to do here,” she said. “Yes, Donald Trump sexually assaulted Ms. Carroll. Yes, he defamed her over and over again. Yes, her reputation suffered. And yes, she gets death threats or, as Ms. Habba called them, mean tweets. But they want you to decide that that’s Ms. Carroll’s fault, that somehow Donald Trump is the victim here.”
Trump’s face contorted, and he appeared to say the word: “True.”
Crowley closed by asking the jury to “make him pay enough so that he will stop.” In the end, they had to deliberate for only a few hours before delivering their reckoning: $18.3 million in compensatory damages, less than what the plaintiffs had requested, but also a staggering $65 million in punitive damages. The punishment was delivered. Perhaps anticipating what was coming, Trump had left the courthouse in his motorcade earlier in the afternoon, so he didn’t hear the verdict. He left it to Habba to address the cameras outside the courthouse, where she complained about an unfair judge and “that ridiculous jury.”
“Don’t get it twisted. We are seeing a violation of our justice system,” Habba said. “Everybody has a right to defend themselves when they are wrongly accused and to be able to say, ‘I didn’t do it.’ And to double and triple and quadruple down, and say, ‘This is wrong.’”
Habba said she was “proud to stand with President Trump.” After the trial, she and other members of his defense team said they looked forward to another verdict from the voters. They pointed to polls suggesting that Trump’s legal troubles were galvanizing to his Republican supporters, who accepted his claims of persecution. “We are in the state of New York,” Habba said. “And that is why we are seeing these witch hunts, these ‘hoaxes,’ as he calls them.”
Trump was already aboard his plane, preparing to transition back from the trial to the trail. His personal stake in the coming election had just risen even higher. If he wins, he will presumably recover his legal immunity, allowing him to squash the criminal prosecutions he faces and possibly complicating the years-long appeals process for his civil cases. If he loses, Trump could also end up being stripped of his fortune, his business, his dignity, and his freedom.
“It will not deter us,” Habba said, sounding like a campaigner. “We will keep fighting. And I assure you we didn’t win today, but we will win.”
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