Legal experts weigh in on Trump’s options after failure to secure $464M appeal bond: ‘uncharted territory’

Legal experts are weighing in on Donald Trump’s options after attorneys for the former president said he has not been able to secure a $464 million appeal bond he needs following a New York civil fraud judgment against him. 

Trump’s lawyers wrote in a Monday court filing that obtaining the nearly half-a-billion appeal was a "practical impossibility under the circumstances presented." 

David Gelman, a criminal defense attorney and a former deputy district attorney, called the judgment a "unicorn." He argued that the judge should give Trump a lot more leeway to satisfy the bond because "not even the richest man in the world has $464 million lying around." 

A New York Appeals Court judge denied Trump’s request late last month to delay payment of the $464 million owed as a result of the lawsuit brought by New York State Attorney General Letitia James, but said he would temporarily allow the 2024 front-runner and his sons to continue running their business during the appeals process. 

A New York Appeals Court judge previously ruled that the former president must post a bond for the full amount of the judgment and that an independent director of compliance will be appointed.  

That ruling comes after New York Judge Arthur Engoron handed down his decision earlier in February after a months-long trial beginning in October in which the former president was accused of inflating his assets and committing fraud in financial documents.

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Engoron ruled that Trump and other defendants were liable for "persistent and repeated fraud," "falsifying business records," "issuing false financial statements," "conspiracy to falsify false financial statements," "insurance fraud" and "conspiracy to commit insurance fraud."

Gelman told Fox News Digital that "everyone needs to realize how unprecedented this is." 

"There has never been a judgment of this magnitude against a company or individual in the history of New York, so we are really in uncharted territory." 

Gelman said Trump has three options: not appeal, ask the court to allow Attorney General James to use his property as collateral, or take it to a federal court and say the New York law is unconstitutional on its face. 

"Courts really don’t deny bonds when there are other ways to pay. Again, because this is so unprecedented, and I don’t care how rich you are, nobody has that much liquid cash. So if a court had the option to allow a defendant to use some other collateral to satisfy the bond, they will," Gelman said. 

He added that there was no reason for the judge or Attorney General James to say no. 

"You’re dealing with Trump. He’s not going anywhere. He’s the most famous and well known person in the world. It’s not like he can just disappear and can’t be found," Gelman said. 

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Former federal prosecutor Andrew Cherkasky told Fox News’ The Story with Martha MacCallum that he "would not count Trump out yet." 

Cherkasky said that even if the court denies Trump’s appeal, he "still has paths to move forward through federal court – ultimately to the Supreme Court to complain about Eight Amendment violations." 

Per the Eighth Amendment, which deals with cruel and unusual punishment, "excessive bail shall not be required, nor excessive fines imposed, nor cruel and unusual punishments inflicted." 

Cherkasky argued that the fines imposed on Trump were so "astronomically high here that it seems unbelievable for the Constitution to permit it under these circumstances." 

"I think – and I hope – that the New York Court of Appeals looks at it appropriately," Cherkasky said. "But like I said, I think even the Supreme Court would have an interest in this case on Eighth Amendment grounds." 

Trump attorney Alina Habba told the X22 report Monday she was "confident" Trump's debt would be dismissed. 

"Despite the fact that witnesses frankly had said that they were great clients, we all made money, they did nothing wrong, we got slammed with this egregious number, and I'm confident we'll overturn it," Habba told the online podcast. 

Writing on his Truth Social platform later Monday, Trump called the bond set by Engoron "unconsitutitonal, un-American, unprecedented, and practically impossible for ANY company, including one as successful as mine." 

"The Bonding Companies have never heard of such a bond of this size before nor do they have the ability to post such a bond, even if they wanted to," Trump wrote. 

Fox News' Greg Norman contributed to this report.