Trump biographer says ex-president is about to be 'exposed' by $454M fine and claims it will 'open the kimono' and reveal Donald to be poorer than he lets on

Donald Trump's biographer claims the former president's finances will soon be exposed as a sham, thanks to a $454m fine he owes the State of New York

Tim O'Brien told MSNBC: 'Now, here we are in 2024, and he is about to get exposed.

'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 has implied Trump - whose net worth is estimated at $2.6 billion - has access to far less liquid cash than he claims. New York Attorney General Letitia James is said to be eyeing up seizing one of the former president's golf clubs and a country estate as collateral. 

Trump was fined $464m for inflating the value of his assets to gain more favorable loan terms. He's appealing that ruling, but must cough-up $557 million bond by Monday, with seizure of his assets likely if he cannot.  

Trump has until Monday to come up with his $454 million bond before the state can start seizing his property

In February, as the highly contentious legal battle drew to a close, New York Judge Arthur Engoron, found that Trump and some of his business associates had illegitimately inflated the value of his assets to obtain more favorable terms from lenders and insurers.

Judge Engoron, who had previously imposed a gag order on Trump after he posted a derogatory comment about the judge's law clerk on social media, ordered the former president to cough up roughly $355 million in penalties for fraud, plus interest. 

With interest, the amount Trump owes is in excess of $464 million. Trump has maintained his innocence and intends to appeal the ruling. 

Tim O'Brien, a senior editor at Bloomberg, wrote TrumpNation, a Trump biography that was published in 2005

AG Letitia James has already initiated the process whereby the state can seize Trump's property

The former president has until Monday to post his nine-figure bond, an eye-watering sum which Trump has had trouble coming up with. Chubb, the insurance company that underwrote Trump's $91.6 million bond in the E. Jean Carroll case, told the Republican frontrunner's legal team that they were not an option.

If Trump doesn't make his payment in full or secure a bond by Monday, New York AG Letitia James can start seizing his property.

On Friday, the New York attorney general's office filed judgements in Westchester County, where Trump's New York golf course and private estate are located.

Entering a judgment is the first step a creditor would take to try to recover a property. AG James' decision to enter a judgement in Westchester is an unmistakable sign that the state is preparing to seize the former president's property.

Judgments have also been filed in New York City, where Trump's other holdings, including his prized possession, Trump Tower, are located.

Trump has this weekend to try to figure out a way to extricate himself from this situation. His lawyers have said that the former president has faced 'insurmountable difficulties' in trying to come up with the bond.

Trump's Seven Springs estate, north of Manhattan, is one of the properties the attorney general's office is prepared to seize

Seven Springs sits on 370 tranquil acres in Westchester County

The attorney general's office is eyeing Trump's New York golf club, also in Westchester

Joining Lawrence O'Donnell on his MSNBC program, Trump's former biographer said that the true state of Donald Trump's financial affairs was about to be revealed.

Trump has tried to counter claims that he doesn't have enough money to pay the bond. Despite his lawyers saying in a court filing on Monday that he had been unable to secure a bond, Trump wrote in a Truth Social post on Friday that he had almost $500 million in cash.

His post, which was written in all caps, said: 'Through hard work, talent, and luck, I currently have almost five hundred million dollars in cash, a substantial amount of which I intended to use in my campaign for president.'

O'Brien, who is currently a senior executive editor at Bloomberg Opinion and was previously a reporter for the New York Times, wrote TrumpNation: The Art of Being the Donald, a biography that was written with Trump's cooperation and was published in 2005.

In his television appearance on Friday, O'Brien recounted a conversation he'd had with Trump in which the former president discussed his past and expressed regret over declaring bankruptcy.

Trump's lawyers said in a court filing on Monday that the team had been unable to secure financial backing for the bond

O'brien said that Trump's wealth is smaller than he lets on and that the former president 'is about to get exposed' by the $454 million bond

'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 remembered. ''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.''

Later, the biographer would learn that Trump was allegedly lying when he said that.

'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 said that the civil fraud case was evidence 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.

When O'Brien published his biography on the former president, Trump filed a $5 billion lawsuit against the reporter, seeking $2.5 billion in compensatory damages and $2.5 billion in punitive damages.

Trump's lawsuit centered around a claim O'Brien made in his book in which he contended that Trump was not a billionaire but instead had a net worth that ranged from  $150 to $250 million. 

Trump's pugnacious lawsuit, which had all the hallmarks of the Roy Cohn legal playbook, was dismissed by a judge in 2009, a decision that was affirmed by an appeals court in 2011.

Trump has tried to stifle the impression that he can't make bond by posting on Truth Social that he has almost $500 million in cash

Trump and O'Brien had a legal spat when the biographer's book was published because the former president took exception with O'Brien's claim that he wasn't a billionaire 

Trump tries to project an image of unassailable wealth, and O'Brien felt that the former president's extravagant reaction to the biography's claims about his net worth stemmed from his desire to maintain that image. 

In an interview with the Washington Post from 2016, O'Brien observed that only a few pages in the biography explored Trump's net worth.  

He said that Trump's frustration about the claim was 'a measure of his deep insecurity.'

'His wealth and the size of his wealth...are integral to how he wants people to perceive him,' O'Brien said.

If Trump fails to come up with $454 million on Monday, that image will be dealt a major blow.