Jack Smith

Faced with having to pay writer E. Jean Carroll $88.3 million in total damages as the result of two separate trials related to sexual assault and defamation, Donald Trump is facing an overwhelming cash crunch should Judge Arthur Engoron also slam him with millions more in penalties in the still-to-be-concluded financial fraud trial.

In an interview with former U.S. Attorney Joyce Vance, former Trump biographer Tim O'Brien speculated that the former president has approximately $600 million that he can tap into — but he could be looking at penalties close to $460 million that would devastate the former president if he is forced to pay up.

O'Brien, who has investigated Trump's financial status for years, claimed losing all that cash would be "a tough pill to swallow, even for somebody with Trump’s resources."

Speaking with Vance, O'Brien stated Trump may be worth close to the $3.1 billion that outsiders have estimated, but coming up with money will be no easy task and E. Jean Carroll's legal team may have to force the issue once all Trump's appeals are exhausted.

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"Only about $600 million or so of that amount is in highly liquid holdings like cash. He can’t easily sell his stakes in some real estate ventures, so he’ll have to extract the payment from his cash hoard, most likely," he explained. "But he’ll hate having to do that and will resent it. So, lawyers and prosecutors may have to file liens against some of his assets so E. Jean Carroll can be paid.

The biographer also suggested Trump fears losing his fortune more than he fears the prospect of jail time looming in the Georgia RICO trial and the two federal cases being brought by special counsel Jack Smith.

"That’s because massive amounts of money aren’t in play in those cases – just possible prison 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," he stated before adding, "At its core, however, is fear. The system finally caught up to Trump — in his 78th year. It’s also still unclear whether he might successfully run the clock out on those prosecutions."

You can read more here at Vance's Substack platform.

Donald Trump's frustration with his myriad legal problems boiled over early Saturday morning and he unleashed an attack on special counsel Jack Smith and New York Attorney General Letitia James, among others, accusing them of criminality for hauling him into court.

The former president has been uncharacteristically silent on his Truth Social platform, aside from posting memes and polls showing him beating South Carolina's Nikki Haley for the GOP's 2024 presidential nomination, after losing a $83.3 million to writer E. Jean Carroll in a defamation trial.

On Saturday morning, he broke his silence about his legal woes, while notably avoiding any mention of his Carroll loss, calling those who have investigated him, "bad people who hate our Country."

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Misspelling Fulton County Fani Willis' name, he wrote, "Deranged Jack Smith, Leticia (sic) 'Peekaboo' James, Alvin Bragg, the J6 Committee of Political Thugs (who have deleted and destroyed all evidence and findings), and all of the rest of the Biden prosecutors and “bad people who hate our Country,” are just as guilty as Fani Willes (sic)."

He then added, "It’s Biden Investigations for purposes of ELECTION INTERFERENCE. MAKE AMERICA GREAT AGAIN!"