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Trump is scrambling to keep his fortune from slipping away

And complicating a big windfall for Trump are two former ‘Apprentices’ and business partners who should've known what they were getting into.

The two former “Apprentice” contestants probably should have known this was not going to end well.

Andy Litinsky and Wes Moss had each heard “You’re fired” from Donald Trump during Season 2 of “The Apprentice,” and they could have left it at that. But they decided to try to get back into business with Trump, anyway.

Litinsky and Moss’s lawsuit now threatens Trump’s much-needed payday.

Years later, after Trump The Reality Host had become a twice-impeached former president under investigation for attempting to subvert democracy, Litinsky and Moss decided to go into business with their former boss. With Trump, they formed a company called United Atlantic Ventures and helped him build Truth Social, his off-brand alternative to Facebook and Twitter. Perhaps more than anything else, it was a business born from necessity: After all, both Twitter and Facebook had kicked Trump off their platforms.

Last week, we got reporting that Litinsky and Moss are now suing Donald Trump. They claim Trump is essentially trying to cheat them out of their share of the company, just as it’s about to go public and potentially net Trump billions of dollars — if he can sell his shares. And Litinsky and Moss’s lawsuit now threatens Trump’s much-needed payday. He’s a man who is on the hook for more than half a billion dollars in judgments from both civil fraud and defamation lawsuits. 

Trump is appealing those judgments, but while the case makes its way through the appellate process, he is supposed to pay the amounts awarded to the plaintiffs.

That doesn’t mean he will. 

This week, Trump tried to get a federal court in New York to delay enforcing the $83 million he owes after losing a defamation case filed against him by writer E. Jean Carroll. On Thursday, Carroll’s attorneys argued that Trump should be forced to pay, saying he had offered no explanation as to why he can’t pay and no guarantee that he one day will. “He simply asks the Court to ‘trust me’ and offers … the court filing equivalent of a paper napkin; signed by the least trustworthy of borrowers,” they wrote. 

He simply asks the Court to ‘trust me’ and offers … the court filing equivalent of a paper napkin; signed by the least trustworthy of borrowers."

Lawyers for E. jean carroll

Trump is also trying to avoid paying the $454 million he has been ordered to pay by a New York state judge in the civil fraud case against him, two of his sons and the Trump Organization. This week, Trump’s attorneys asked the court to allow him to pay only $100 million of that judgment, arguing that he doesn’t have the full amount and would be forced to sell real estate holdings at fire-sale prices to make good on it. The court flatly denied that request in a terse statement, saying, “You have failed to explain, much less justify, any basis” for delaying the payment.

If Trump’s traditional delay tactics aren’t working, that doesn’t mean he’s given up trying to avoid forking over what’s due.

On Wednesday, we learned about what could be yet another attempt by Trump to avoid paying the piper. In a legal filing, first reported by The Daily Beast, New York Attorney General Letitia James accuses Trump of quietly trying to move his assets to Florida to avoid having them seized by the state. She writes, “After the court issued its February 16 order, defendants announced for the first time that various Trump Organization entities operating in New York ... are allegedly now located in Florida.”

As of 2023, two of the companies that were part of James’ lawsuit, DJT Holdings LLC and DJT Holdings Managing Member LLC, were located in New York. Both have now been relocated to Florida. 

Did Trump move those companies to Florida after the attorney general brought a lawsuit against him and his companies? That would be one creative way to try to get out of paying any penalties. But it would not be unforeseen. Indeed, it’s something the judge in the case, Arthur Engoron, was apparently worried might happen and explicitly aimed to prevent. At the very beginning of the trial, Engoron barred Trump from moving assets out of state.

We already know that Trump is doing everything in his power to avoid accountability in his civil and criminal trials. In some cases, it is working: Both criminal prosecutions of the former president brought by special counsel Jack Smith, as well the criminal case in Fulton County, Georgia, are all in danger of being stalled until after this November’s election.

The civil cases against Trump — the ones from the New York attorney general and from Carroll — have been the only cases so far in which Trump has really had to face justice.

And now he’s making several last-ditch efforts to avoid having to pay up. So far, though, whether it’s the judges — or the formerly fired reality TV stars Trump was once in business with — none of it has worked.

This is an adapted excerpt from the March 1 episode of “Alex Wagner Tonight.