Pleading the Eighth? Ex-federal prosecutor says don't 'count Trump out yet' despite massive fine

As former President Trump continues to fight legal battles on multiple fronts, conjecture arose that the massive fine levied against him by New York Supreme Court First District Judge Arthur Engoron might be the straw to break the presumptive Republican nominee's back.

On Monday, Trump's attorneys said he has not been able to secure a $464 million appeal bond he needs following a New York civil fraud judgment against him. In a court filing, Trump's team said obtaining one is a "practical impossibility under the circumstances presented."

However, at least one prosecutor said despite appearances, the former president may have a sound legal case to shrink or put aside the $464 million bond that New York State Attorney General Letitia James said she will seek to otherwise enforce as he appeals.

"I would not count Trump out yet," former federal prosecutor Andrew Cherkasky told "The Story" on Monday.

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"He has a week yet to actually have this money secured in order to file the appeal," Cherkasky said.

The former U.S. Air Force judge advocate general noted Trump is already attempting to get a court's approval for a $100 million bond amount instead or procure a ruling nixing the bond entirely.

The Constitution, Cherkasky said, appears to be in Trump's corner.

With the bond and fine being as high as they are, Trump has a potential Eighth Amendment defense, as James has threatened to begin seizing his New York assets, which include The Trump Building at 40 Wall Street, a large stake in a commercial skyscraper, plus his iconic Trump Tower.

The Eighth Amendment decrees "excessive bail shall not be required, nor excessive fines imposed, nor cruel and unusual punishments inflicted."

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Judge Anil Singh, an Andrew Cuomo appointee to the state's appellate court, dealt another judicial blow to Trump in late February when he denied the former president a pause in the collection of the bond.

Singh, however, decided he would allow Trump and sons Eric and Don Jr. to continue running the family business during the appeals process – as Engoron has banned them from operating in New York for several years hereforth.

"[If] James actually does try to foreclose on some of his properties, I think he still has paths to move forward through federal court, ultimately to the Supreme Court to complain about Eighth Amendment violations," Cherkasky told "The Story."

The prosecutor added it seems "unbelievable" the Constitution would permit such a lien against Trump.

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"It does seem very unusual to have to essentially disgorge yourself of everything that you're still fighting for through the appellate channel," he said, noting Trump appears counter to the typical defendant attempting to delay or decrease fine enforcement.