'He was lying to me': Trump biographer recounts how ex-president misled him about loans

He reportedly keeps lying and never learns his lessons.

Donald Trump biographer Tim O'Brien, appearing on MSNBC's "The Last Word" with Lawrence O'Donnell, recounted a time when he was walking and talking at Mar-a-Lago with former President Donald Trump more than decade before he'd run for office.

The two were talking about the past and regrets especially about declaring bankruptcy.

ALSO READ: Here's why conservative elites are bailing on Trump now

Trump had a few.

"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. 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.'"

Only O'Brien later learned he was being sold a bunch of bad goods.

"I later found out he was lying to me in that very moment," he said. "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."

It was "a few years later" when O'Brien learned he had supposedly been lied to.

"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."

Trump is facing a Monday deadline to come up with $464 million bond as a result of the damages Manhattan Supreme Court Justice Arthur Engoron determined he owed for a case that Attorney General Letitia James prosecuted blaming him and his company, The Trump Organization, for committing years of fraud by hyping up the value of his assets to secure sweet loans and deals.

That decision is being appealed by the former president's attorneys.

O'Brien said it's a long pattern.

"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."

So even if Trump fails to remit the incredible amount that is being asked of him, O'Brien believes the damage has been done to break through the real estate tycoon's Teflon veneer.

"It is a demonstration he doesn't learn his lessons," said O'Brien. "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."

Watch below or click the link.