'Stunningly embarrassing': Legal expert baffled by Trump's $464M bond problems

Former President Donald Trump's civil fraud trial bond troubles are exposing him to more scrutiny, and ridicule too, a legal expert said Thursday.

Former prosecutor and Pace University law professor Bennett Gershman told Salon Thursday he was baffled by Trump's recent announcement that he could not find an insurer to back the $464 million payment due Monday in his New York civil fraud case.

"I find it strange that Trump is essentially claiming that he either does not have sufficient assets to cover a bond or that bonding companies don’t trust him," Gershman added. "Either claim is stunningly embarrassing to someone who has flaunted his wealth and power."

Gershman posited the presumptive GOP presidential nominee might be "lying" or reluctant to "squander limited assets" he'll need to fuel his bid to reclaim the White House.

The former prosecutor also wondered if Trump's "lengthy history of his business fraud and numerous bankruptcies" raised red flags.

Thirty companies have declined to underwrite Trump's civil fraud judgement, ordered last month by Justice Arthur Engoron, after he was found liable for defrauding lenders and investors by inflating the value of Trump Organization assets.

Trump has filed a notice of appeal, but must still hand over cash or bond on March 25 to ward off state Attorney General Letitia James potentially padlocking his assets.

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That's why in a filing earlier this week, Trump asked for a stay on the payment as he pursues his appeal. In a response, James' team knocked Trump's filing in a response requesting the appeals court ignore it.

James also threw some shade, suggesting Trump could not secure a loan because no one wanted to take his property as collateral.

"As far as the Court can infer, sureties may have refused to accept defendants' specific holdings as collateral because using Mr. Trump's real estate will generally need 'a property appraisal' and his holdings are not nearly as valuable as defendants claim," James' response reads.

Gershman suspects the companies Trump's tried to woo may have "good reason" for refusing "to underwrite the entire amount" of his judgment because they "probably don't trust" the former president's numbers based on the civil fraud case ruling.

Meanwhile, Syracuse University College of Law professor Gregory Germain told Salon that whatever the reasons behind the ruling, and despite being given more than a month to cough up the dough, it's "not reasonable to expect someone to be able to post a half-billion-dollar bond on short notice."

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