Donald Trump Biographer Predicts He'll Be 'Exposed' by Bond Deadline

Tim O'Brien, Donald Trump's biographer, said on Friday that he believes the former president will be "exposed" by having to pay the $464 million he owes to the state of New York after a court found him liable for fraud in a civil case.

New York Judge Arthur Engoron found Trump and some of his business associates had illegitimately inflated the value of his assets to obtain more favorable terms from lenders and insurers. In February, Engoron ordered the former president to pay roughly $355 million in penalties for fraud, plus interest. With this, the payment exceeds $464 million. Trump has always denied any wrongdoing and will appeal the ruling.

Trump, the presumptive 2024 Republican presidential nominee, has until Monday either to put up the cash in full or to secure a bond before New York Attorney General Letitia James can start seizing his property.

Earlier this week, Trump's legal team said that he had faced "insurmountable difficulties" in trying to raise the bond. His properties, including Trump Tower and a number of his golf courses, could be seized, unless he can find a solution over the weekend.

Appearing on MSNBC's The Last Word With Lawrence O'Donnell, O'Brien said Trump is following a pattern that dates back decades.

"Now, here we are in 2024, and he is about to get exposed," he said. "It is going to be a slow grind. I don't think there's going to be a lot of drama on Monday. But the process of opening the kimono and discovering indeed Donald Trump has no financial clothing, at least not the kind of financial clothing he claims he's had, begins."

O'Brien, who is currently a senior executive editor at Bloomberg Opinion, has reported on Trump's financial status for years as he was also a reporter with The New York Times. He's also the author of TrumpNation: The Art of Being the Donald.

Newsweek reached out to the Trump campaign on Saturday morning. This story will be updated with any provided statements.

O'Brien, a critic of Trump, also told O'Donnell about an instance at Mar-a-Lago when the former president told him about his past and regrets about declaring bankruptcy.

"He said, 'You know, my father always said, 'You never personally guarantee any loans.' And I made a mistake. I personally guaranteed too much money in the early 1990s," O'Brien recalled. "'I didn't think it would catch up with me. And it did. And I learned my lesson. I would never personally guarantee a loan after that.'"

O'Brien said he later learned that Trump was allegedly lying in that moment.

"I didn't know it, but it turned out he had personally guaranteed some of the loans on the new building he was developing in Chicago. So, he goes through these searing moments where he almost loses everything he can and has, and he says: 'I learned these lessons; I should've listened to my father.' Lo and behold, he is doing the same thing."

O'Brien believes the civil fraud case and its fallout is a demonstration that Trump "doesn't learn his lessons."

"He does not anticipate problems properly. He doesn't do it because he is a juvenile delinquent; he lacks the maturity, wisdom and strategic insight of an adult," he said.