The prospect that Donald Trump may fail to post a bond by Monday’s deadline for the $464 million civil fraud penalty against him and his co-defendants has frustrated the former president and some members of his inner circle, a Trump ally and two campaign sources familiar with the situation told NBC News.

Trump, the billionaire developer who is seeking a return to the White House, finds himself in the unprecedented position of hitting up high-dollar donors not just for campaign cash — for which he has an urgent political need — but also to see whether they might guarantee his bond, according to a Trump ally who received such a call from a member of the presumptive GOP nominee’s team. The source asked not to be named to speak candidly about sensitive conversations.

New York state Judge Arthur Engoron’s ruling in Trump’s civil fraud trial was made official Feb. 23, starting the clock on a 30-day automatic stay of the judgment. That period is set to expire Monday, at which point New York Attorney General Letitia James could start seizing Trump’s assets unless an appeals court steps in.

Failure to secure a bond by Monday’s deadline could lead the state to seize Trump’s bank accounts or properties — from Trump Tower in midtown Manhattan to his resorts, golf courses or plane.

In a filing Monday, Trump’s attorneys said securing a bond for nearly a half a billion dollars by next week’s deadline was “a practical impossibility,” despite their best efforts — including “approaching about 30 surety companies through 4 separate brokers.”

Their petition to pause enforcement of Engoron’s judgment is still pending before an appellate court, which could intervene on his behalf.

A source close to the Trump family said Trump’s defense team is gaming out its options, including ways Trump could appeal Engoron’s ruling without having to put the bond up and what would happen if they can’t secure the required sum. There’s also the belief that seizing Trump’s assets or liquidating them at “fire sale” prices, as Trump has warned, could prove to be rocket fuel for his campaign.

“They’re looking to appeal the actual requirements to have to put up this amount of money to appeal and then, obviously, the appeal itself on grounds it’s a violation of the Eighth Amendment,” the source said. “They have to figure all those machinations out.”

The Trump campaign didn’t immediately respond to a request for comment.

Monday’s filing seeking to pause execution of the $464 million judgment was filed on behalf of Trump and his co-defendants, including his sons Donald Jr. and Eric, who have been running the Trump Organization since their father took office in 2017.

State attorneys have argued that Trump intentionally overstated his wealth on loan applications. His critics have tried to use the civil fraud case to undermine his business image, and they may seek to capitalize on the notion that he can’t afford to pay the bond.

Trump has raged against the judge’s and James’ handling of the case on his social media platform, attacking a “corrupt Communist system” late Monday and then writing Tuesday morning: “I would be forced to mortgage or sell Great Assets, perhaps at Fire Sale prices, and if and when I win the Appeal, they would be gone. Does that make sense? WITCH HUNT. ELECTION INTERFERENCE!”

“You can’t reverse selling off Trump Tower on a fire sale at a discounted price,” Trump attorney Alina Habba said in a Fox News interview Wednesday. “We can’t fix that if we win on an appeal. So it’s complete injustice.”

But while Trump’s attorneys and accountants may be fretting over the bond issue, his campaign has leaned into it, as it has with his other legal battles. The campaign fired off an “emergency memo” fundraising appeal Wednesday with the heading “Keep your filthy hands off of Trump Tower.”

“Insane radical Democrat AG Letitia James wants to SEIZE my properties in New York. THIS INCLUDES THE ICONIC TRUMP TOWER!” the call for donations to the Trump joint fundraising committee reads in part.

Some of Trump’s allies believe the images of agents of the state of New York attempting to seize his properties would only further galvanize supporters and lend weight to their argument that he’s being unfairly targeted by the justice system.

Such a move would provide a “massive” boost to the Trump campaign, longtime Trump adviser Steve Bannon told NBC News on Wednesday.

“She’s not that dumb,” Bannon said of the possibility that James would authorize seizing Trump’s assets.

The source close to the Trump family said that for Trump’s advisers, “that is part of the calculation — whether this continues to help or if, in some way, it hurts him. The one way is if it affects the pocketbook or the case.”

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