What Donald Trump Fears More Than Jail, According to His Biographer

Donald Trump may fear the financial impacts of his civil defamation and civil fraud trials more than the possibility of jail time, according to the former president's biographer Tim O'Brien on Friday.

In Trump's second civil defamation trial, a New York City jury ordered last week that he must pay $83.3 million in damages to E. Jean Carroll for statements made in 2019 when he claimed she was lying about allegations that he sexually assaulted her inside a Manhattan department store dressing room in the 1990s. That amount includes $7.3 million in compensatory damages, $11 million for reputational repair, and $65 million in punitive damages. Trump was previously ordered to pay Carroll $5 million in damages last year in another civil defamation trial stemming from a denial he made about her claims in 2022.

In a Truth Social post after last week's verdict, the former president wrote that he disagrees with both verdicts and "will be appealing" them.

In addition, Trump is facing a civil fraud trial brought by New York Attorney General Letitia James. In September, Judge Arthur Engoron issued a partial summary judgment ruling that Trump and top executives at The Trump Organization committed fraud. He held that the former president grossly inflated the value of his assets to obtain more favorable terms from lenders and insurers. James is asking for $370 million and for Trump to be permanently barred from doing business in New York. Trump has maintained his innocence and claimed the case is politically motivated as he is the GOP frontrunner in the 2024 presidential race.

Although Engoron was expected to make a ruling by the end of January, a New York court spokesperson said on Thursday that a verdict will not be reached until early to mid-February, adding that the new deadline is "subject to modifications."

In an interview with former U.S. Attorney Joyce Vance that was published to her Substack on Friday, O'Brien discussed the potential financial impacts of both civil trails, adding that he believes Trump fears the financial ramifications more than the possibility of jail time stemming from his criminal cases.

"The financial judgments absolutely bother him. Trump sees his life, himself, his relationships and the world around him through the lens of money. It animates everything he does," O'Brien said.

He added: "I think these cases might bother him more than the two federal cases connected to the Jan. 6 insurrection and possible misappropriation of classified documents. They also bother him currently more than the voting fraud case in Georgia. And that's because massive amounts of money aren't in play in those cases – just possible prison time."

Newsweek has reached out to Trump's spokesperson via email for comment.

Trump is facing four criminal indictments with a total of 91 charges, all of which he maintains his innocence in, while calling them part of a political witch hunt. One of them is a Georgia racketeering case in which he and 18 co-defendants were charged last year of trying to overturn the results of the 2020 election in the state. While another is his election interference case in Washington, D.C. Special counsel Jack Smith has led the Department of Justice (DOJ) investigation, accusing Trump of attempting to overturn the results of the 2020 presidential election that led to the U.S. Capitol riot on January 6, 2021.

In addition, Trump is facing dozens of felony charges from the DOJ, accusing him of unlawfully retaining classified documents at his Mar-a-Lago estate in Florida after leaving the White House in 2021 and repeatedly obstructing government efforts to retrieve them.

The former president has vowed to stay in the presidential race even if he is convicted of a crime, as he is legally allowed to run.

Although O'Brien, who has reported on Trump's financial status for years as he was also a reporter with The New York Times, said that the financial impact would be "a tough pill to swallow," he believes it doesn't mean the former president doesn't also fear jail time.

"But I don't think that means Trump still doesn't fear and resent the possible outcomes in the federal and state cases; he certainly does. He's afraid of being found guilty and of serving time; hence the carping about being a victim and all of the performance art targeting judges and the system," O'Brien, who is currently a senior executive editor at Bloomberg Opinion, said.

His comments come after attorneys have previously told Newsweek that the defamation damages in combination with potential damages from his civil fraud trial could drive Trump to bankruptcy.

"Only Trump knows for sure what his finances actually are. But the combination of the New York civil fraud case and the E. Jean Carroll cases could be a one-two punch that triggers a bankruptcy. However, I doubt ex-President Trump would want to file for bankruptcy during an election year," Ciara Torres-Spelliscy, an associate professor of law at Stetson University College of Law, said.

Attorney Bradley Moss previously told Newsweek that, while the issue was outside his area of expertise, he doubted the case would bankrupt Trump.

"I do not expect this to bankrupt him," he said. "He does have actual assets."