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Attorneys for Donald Trump say finding a bond to cover the $464m (£365m) judgment in his New York fraud case is a “practical impossibility”.
A New York judge ordered Mr Trump to pay the penalty in February for falsely inflating his assets.
Mr Trump had offered to post a smaller bond, for $100m, while appealing the case, but a judge denied that request.
Mr Trump’s lawyers said they approached 30 companies to back the nearly half-billion dollar total, with no luck.
“The amount of the judgment, with interest, exceeds $464 million, and very few bonding companies will consider a bond of anything approaching that magnitude,” his attorneys wrote in a nearly 5,000-page filing.
They are asking a judge to put the judgment on pause while Mr Trump appeals the decision.
“The practical impossibility of obtaining a bond interferes with defendants’ right to appeal,” his lawyers added.
Mr Trump’s two eldest sons also must pay millions of dollars in the case.
Along with ordering Mr Trump to pay the penalty, New York Judge Arthur Engoron banned him from running any businesses in the state for three years after he found the former president falsely inflated assets to secure better loan deals.
A judge paused Mr Trump’s business ban last month but denied his bid to provide a smaller bond amount to cover the fine.
In the latest filing, the former president’s lawyers included an affidavit from a president of a private insurance firm, who said that “simply put, a bond of this size is rarely, if ever, seen”.
“In the unusual circumstance that a bond of this size is issued, it is provided to the largest public companies in the world, not to individuals or privately held businesses,” the president also said.
Mr Trump’s attorneys added they had spent “countless hours negotiating with one of the largest insurance companies in the world” with no success.
They also said bond companies would not accept “hard assets such as real estate as collateral” for the bond, but only cash or “cash equivalents”, such as investments that can be quickly liquidated.
According to a Forbes estimate, Mr Trump is worth about $2.6bn. He also testified last year he has $400m in liquid assets.
But the $450m judgment is not his only expense. He was ordered to pay $83m in January after losing a defamation case to E Jean Carroll, a woman he was found to have sexually abused. He has already posted a bond in that case.
New York’s attorney general has vowed to seize his assets if he doesn’t pay the fraud judgment.
The penalty will keep accruing interest by at least $112,000 per day if he refuses to pay.
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