Donald Trump Likely to Declare Bankruptcy: George Conway

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Donald Trump is likely to declare bankruptcy to delay paying the $355 million plus interest in penalties imposed by Judge Arthur Engoron last week, according to experts including attorney George Conway.

Conway, board president of the Society for the Rule of Law Institute and husband to former White House adviser under Trump, Kellyanne Conway—they announced they were divorcing—responded to a post on X, formerly known as Twitter, suggesting the former president’s next move might be to declare bankruptcy.

“Bankruptcy is Donald Trump’s likely next legal move to delay paying more than $500 million in damage awards,” wrote on the social media platform David Cay Johnston, an investigative journalist and Syracuse Law lecturer.

Conway responded to Johnston’s post saying that “the odds of this happening are fairly high.”

On Friday, Judge Engoron, who was overseeing the New York Attorney General Letitia James’ civil fraud case against Trump, ordered the embattled former president to pay $355 million plus interest in penalties for inflating the value of his assets in order to get more favorable terms from banks and insurers. The New York judge, a Democrat, also banned Trump from serving as officer or director of any company in the state for three years, while his two eldest sons were banned for two years.

Trump was also recently ordered to pay $83.3 million for defaming writer Jean E. Carroll. In May 2023, Trump was found liable for sexually assaulting her in a New York department store in the mid-1990s.

Former President Donald Trump speaks during a Fox News town hall on February 20, 2024 in Greenville, South Carolina. A television screen shot on February 5, 2020, shows attorney George Conway. Conway agreed that Trump…


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Trump is facing 91 felony counts in four different criminal trials. The former president, who’s currently the frontrunner of the Republican presidential primary, maintained his innocence in all cases, including the New York civil fraud trial.

The former president won’t be forced to pay the sum ordered by Engoron immediately, as he has vowed to appeal.

Newsweek contacted Johnston, the Society for the Rule of Law and Trump lawyer Alina Habba’s firm for comment by email early on Wednesday.

In an article written for DCReport on Monday, Johnston wrote that Trump was likely to follow in the footsteps of conspiracy theorist Alex Jones and former New York City Mayor Rudy Giuliani, who filed for bankruptcy after facing mounting legal costs.

According to Johnston, Trump could file for bankruptcy before March 12 “to delay paying court-ordered awards for defamation.”

Johnston pointed out that Monday, March 12 is the deadline for Trump to appeal to the order to pay $83.3 million to Carroll. “Filing for personal bankruptcy stops the clock on both awards,” wrote Johnston, referring to Engoron’s ruling as well.

While doing so might tarnish the former president’s reputation as a wealthy, savvy businessman, Johnston said, Trump could avoid harming its reputation by telling his followers that he’s doing so to avoid being persecuted by “the Marxist-Fascist-Corrupt-Deep State-Liberal-Radical cabal he blames for his legal woes.”

Bankruptcy might not prevent Trump from eventually having to pay the money he was ordered to pay. Johnston cited Professor Gregory L. Germain, his colleague who teaches bankruptcy law at Syracuse University College of Law, who said it’s likely to get him past Election Day on November 5.