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Former President Donald Trump pledged Monday to overhaul a “third world” justice system if he is elected again, fuming as he confronts massive civil judgments that could wipe out his stores of cash and dent his gold-plated image as a wealthy real-estate icon.

Facing legal challenges that could exceed a half-billion dollars, the first task for Mr. Trump will be to come up with the money within 30 days or post a bond backed by assets, while he appeals a bombshell ruling that says his real estate company manipulated property values to gain favorable terms on loans.

“It looks like his cash will be exhausted. Even if he’s worth a lot more, I cannot imagine a business person having that much cash sitting around,” said David Schultz, a distinguished professor of politics and legal studies at Hamline University in Minnesota. “He will need to sell something or post the bond with part of his real estate assets as collateral.”

It is unclear how far along Mr. Trump is in the process. He is focused on the politics around the judgments, blaming “compromised judges and prosecutors” for his predicament and pledging to make changes if he wins the Republican nomination as expected and defeats President Biden.

“Nothing like this has ever happened in our country before. It is strictly third world, Russia, China at their worst,” he wrote on Truth Social, using all-caps for emphasis. “But fear not, we will win big on November 5th, and Make America Great Again!!!”

Judge Arthur Engoron in New York ordered Mr. Trump to pay $355 million after concluding the ex-president and his oldest sons manipulated the worth of their properties in financial statements. He also barred Mr. Trump from serving as the officer or director of any New York company for three years.

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His sons, Eric Trump and Donald Trump Jr., were barred from similar roles for two years.

“It takes him out of control of his organization, and it makes it difficult for Trump to do business,” Mr. Schultz said. “The other damage was the court opinion essentially pointing to what Trump might really be worth and how much he defrauded others. He might not be able to get anyone to loan him money in the future, and much of his business has been based on debt financing.”

A jury last month required Mr. Trump to pay more than $83 million to former magazine columnist E. Jean Carroll, finding he defamed her after she went public in 2019 with allegations Mr. Trump sexually assaulted her in a New York department store in 1996.

Mr. Trump denies all the allegations against him but faces combined judgments that, with interest, could reach $500 million.

Mr. Trump told Ms. James he was sitting on over $400 million in cash during a deposition last year.

Experts say the judgments, if upheld on appeal, would not bankrupt Mr. Trump since his real estate properties are worth far more. Still, it will be a major cash crunch and another challenge for the ex-president as he navigates a political campaign and thicket of other legal troubles.

The Washington Times reached out to a representative for Mr. Trump‘s legal spokeswoman, Alina Habba, on Monday to learn the status of efforts to secure a bond against the judgments.

The civil judgments could be just the start of Mr. Trump‘s legal troubles this year.

Jury selection is set to begin March 25 in a New York criminal trial that accuses him of falsifying business records to cover up hush-money payments before the 2016 election.

It is one of four criminal trials facing Mr. Trump, though legal delays could push the other trials deeper into the year or past the November election.

Mr. Trump is holding his own, politically, in the meantime. He is the clear front-runner in the GOP primary race that is down to him and former South Carolina Gov. Nikki Haley, and polls show him virtually tied or leading in some cases in a hypothetical rematch against Mr. Biden.

Judge Engoron on Friday imposed the $355 million penalty — payback of what the judge deemed “ill-gotten gains” from his spurious financial statements — and Mr. Trump is required to pay interest on that amount.

At an annual rate of 9%, as prescribed by New York law, that adds up fast.

New York Attorney General Letitia James, a Democrat who led the suit against Mr. Trump, calculates that to date, Mr. Trump owes an additional $98.6 million in interest, bringing his total penalty to $453.5 million. The interest will keep accruing until Mr. Trump pays.

In his ruling, Judge Engoron ruled that the interest Mr. Trump owes on about half of the total penalty amount, pertaining to loan savings, can be calculated from the start of the investigation in 2019. Some interest on the remaining amount, which pertains to more recent transactions, can be calculated starting in May 2022 or June 2023.

Under state law, Mr. Trump will receive an automatic stay of the ruling if he puts up money, assets or an appeal bond covering the amount he owes.

The appeals process typically takes months, if not a year or more. If Mr. Trump is unsuccessful at the Appellate Division, he can ask the state’s highest court, the Court of Appeals, to consider taking his case.

“The question here is how does he prevent these judgments from being collected while the appeal is ongoing,” said Jim Wheaton, a professor at William and Mary Law School who tracks Mr. Trump‘s legal and financial issues. “One is to essentially pay the money into the court and let it sit there, or to get a bonding company — think of it like bail — to put the money up or guarantee the money to the state.”

It could get messy. Properties that could be leveraged to support the bond may have loan covenants that prohibit such uses, or the monitor appointed through Judge Engoron’s court may put strict guardrails around Mr. Trump‘s access to certain funds. However, the bonding company will expect assurances if it decides to work with the former president.

“If I’m the bonding company, I certainly expect to get collateral. I can’t rely on a personal guarantee from him,” Mr. Wheaton said.

Experts said they do not believe the latest judgment could be paid out of campaign funds since the alleged fraud was based on business activity and not his presidential run, although Mr. Trump argues daily that Mr. Biden and Democratic allies are behind his legal woes.

“We can’t allow Crooked or Compromised Judges and Prosecutors to get away with what they are doing to your favorite President, ME, in New York City and State, Fulton County (Atlanta), Georgia, or Washington, D.C. It is a coordinated attack on FREEDOM & LIBERTY,” Mr. Trump wrote. “These cases should all be thrown out!”

This story is based in part on wire service reports.

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