How Trump's 'I'm rich!' boasts are coming back to bite him in court

• Before its $83M verdict, the Carroll defamation jury watched Trump brag on tape about his wealth.
• "We have a lot of cash," the jury watched Trump boast.

When seven men and two women put their heads together in a Manhattan federal courthouse last week, to decide how much of Donald Trump's money to give E. Jean Carroll, they had the benefit of guidance from a top expert on the former president's finances.

That expert was Donald Trump.

The day before awarding Carroll $83.3 million in damages — Trump's penance for calling her a lying "whack job" when she told the world he'd sexually assaulted her — jurors heard, firsthand, how rich he was.

In fact, one of the last things Carroll attorney Roberta Kaplan did before resting her defamation case against Trump was to hit play on a video of him bragging about his stacks of cash.

It was as good as parading Trump before the jury with a "kick me" sign taped to his back.

"We have a lot of cash," Trump boasted in the clip that Carroll's jurors saw last Thursday morning.

"I believe we have substantially in excess of $400 million in cash, which is a lot for a developer," Trump bragged, leaning toward the camera from his seat at a conference table.

"Developers usually don't have cash," Trump eagerly went on. "We have, I believe, 400 plus, and going up very substantially every month."

The clip was from Trump's April deposition in a separate case. It showed him being questioned about his finances by lawyers for the New York Attorney General's office.

"We have great assets," he said in the short deposition clip that jurors saw. "And we have a very valuable company."

Not the smartest legal strategy

Boasting about his tremendous wealth was a questionable legal strategy even back in April, when he was taped doing so.

Most people sitting for depositions speak carefully. But Trump was feeling boast-arous.

His defense against New York's accusations that he fraudulently inflated his wealth to banks was to insist, under oath and on tape, that his numbers should have been even higher.

"You're saying I built up numbers," Trump told state officials in the deposition. "Well, it turned out I didn't because the numbers are much higher than they were."

AG Letitia James has accused Trump of exaggerating his net worth by as much as $3.6 billion a year in a decade's worth of annual financial statements, thereby tricking banks into cutting him a $168 million break in loan interest.

"He's basically sticking his gold-plated foot in his mouth — though I'm not sure it's real gold," said Tristan Snell, who was the lead prosecutor on the New York Attorney General's successful investigation into Trump University.

Trump's "I'm rich" boasts hurt him in both the Carroll verdict and the upcoming fraud trial verdict, Snell said.

In the fraud case, Trump's boasts showed him doubling down on his fuzzy math, he noted. And the same boasts made it easier for Carroll's jurors to hit him up for some of those riches.

Carroll's verdict needed to hurt — or else it would be pointless

In her closing argument, Kaplan said that to deter Trump from continuing to defame Carroll, the jury ought to impose massive punitive damages that would hit Trump where it hurts. After all, Trump didn't deign to show up at last year's trial, where a jury agreed he sexually abused Carroll. He only showed up at this year's trial, where the jury deliberated monetary damages.

"While Donald Trump may not care about the law, while he certainly doesn't care about the truth, he does care about money," Kaplan told the jurors. "As a result, your decision to award a large amount of punitive damages may be the only hope that E. Jean Carroll has to ever be free from Donald Trump's relentless attacks ever again."

When the jury returned a verdict later that day, ordering Trump to pay $83.3 million to Carroll, the vast majority of the sum — $65 million — was in punitive damages. It was significantly higher than last May's verdict, where a different jury said Trump owed Carroll $5 million for both defaming and sexually abusing her. Of that amount, only $280,000 was for punitive damages for the defamation claims.

As Kaplan noted in her closing argument, she wanted the jury to show Trump that he could not "use his wealth and power to defame people whenever he wants."

Punitive damages in defamation cases are supposed to have a deterrent effect, to stop the defamation from happening again. J. Erik Connolly, a defamation attorney representing Smartmatic in its defamation lawsuits over 2020 presidential election conspiracy theories, and who secured the $177 million Disney paid to settle the infamous "pink slime" case, told Business Insider that it would make sense for the jury to take Trump's wealth into account. If the jury thinks a defendant has deep pockets, they can force them to dig into them.

"$1 million in a punitive damages award against the average person could be crushing, but $1 million in a punitive damages award against somebody who boasts of having the wealth that President Trump claims to have would not have a deterrent effect," Connolly, a lawyer at Benesch Law, said.

Hearing Trump in his deposition describe having $400 million in cash, just sitting there, almost certainly impacted their decision, said Snell, whose new book is "Taking Down Trump: 12 Rules for Prosecuting Donald Trump by Someone Who Did It Successfully."

It's what behavioral economics calls "anchoring," Snell said. The idea of anchoring is that the first number people see colors, or anchors, any number they see after that.

"There's actually a lot of science to support this," said Snell, founder of MainStreet.law and a frequent commentator on MSNBC.

"Trump unwittingly anchored the jury onto a bigger number," he added. "I do think it's a narcissistic compulsion on his part to boast about himself beyond all reason and common sense."

Trump's wealth also illustrates why the jury imposed enormous punitive damages compared to the $18.3 million to compensate Carroll.

The jury could be sending a message that Trump ought to be punished for what they determined was his flagrant and habitual lying which, in their verdict, they unanimously decided was "malicious" in their deliberations at the end, court records show.

Connolly said the jurors may be "disgusted by the lack of civility in our public discourse," which Trump carried into the courtroom as he tried to spar with the judge overseeing the trial.

"We've gone into this stage where everyone is almost numb to lying, and that's not a healthy place to be," Connolly said. "So maybe the jury is trying to send a message that we should get back to something a little bit better than what we are right now."

Jurors and judges want verdicts to have bite

In the April deposition, Trump was sure to point out that his cash was just a small part of his wealth. The Carroll jury also heard Trump boast about the value of his "brand."

His very name — "Trump" — adds "billions and billions" of dollars in value to whatever it's placed on, he said in the deposition.

"I mean, I became president because of the brand, okay?" the clip showed Trump saying. "I became president. I think it's the hottest brand in the world."

Between his properties and brand name, the assets Trump described would theoretically total about $14 billion, if you take the former president at his word.

Trump is, in all likelihood, not actually as wealthy as he claims.

For one, he doesn't own the entirety of the Trump Organization, so the Trump Organization's assets don't match up exactly with his personal wealth.

The Trump Organization is private, which normally makes valuations hard to come by. But a spate of lawsuits, financial disclosures as he runs in the 2024 presidential election, an attempted SPAC deal, and tax return leaks have offered a window into his finances.

He is still very wealthy. A recent exhaustive Forbes analysis put his net worth at $2.6 billion. (In his deposition, Trump belittled the Forbes estimation, saying "Forbes doesn't know about us" and that the magazine "has their own agenda.") In January, Bloomberg estimated that Trump had about $600 million in liquid assets.

The jury in Carroll's trial didn't get a more accurate estimate. But it's clear, according to Chris Mattei, a defamation lawyer who secured a $1.5 billion jury verdict against conspiracy theorist Alex Jones, that they took his self-presentation as a wealthy man into account. The jurors also may have decided that the $18.3 million in compensatory damages alone wouldn't have made a big enough dent into Trump's finances.

"Although they didn't have precise information about what assets were available to Donald Trump, they believed a significant punitive verdict was warranted and also one that he could probably pay," Mattei said.

While Trump tried to make him look wealthier in his deposition — and when he took the witness stand in the New York Attorney General's trial against him — it may just work against him.

Arthur Engoron, the New York judge who oversaw the recently completed fraud case, frequently struck Trump's testimony from the record as he rambled about his high property valuations. Mattei thinks Engoron likely won't credit his testimony at all in his impending verdict.

"To the extent he made admissions about his wealth that are inconsistent with representations his company made to banks and others that they did business with — that I think will matter," Mattei said. "But I doubt very much that the judge is going to be crediting as fact his personal estimation of his overall wealth."