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Former President Donald Trump faces a Monday deadline to accomplish the impossible.

If Trump and his adult sons are unable to pay or secure a bond for the $464 million judgment in his civil fraud case — which their lawyers have called a “practical impossibility” — New York Attorney General Letitia James could begin the process of seizing the former president’s prized assets.

The stark possibility follows the AG’s yearslong investigation into the former president’s finances that concluded with an 11-week trial last year. In February, Judge Arthur Engoron found that Trump and his sons had committed a decade of fraud by inflating their assets to obtain better business deals. Trump and his sons have denied all wrongdoing and have appealed the ruling.

The finding and $354 million penalty, plus interest, immediately presented a cash crunch for a man who successfully ran for president on his wealth and success.

“I mean I became president because of the brand, OK? I became president. I think it’s the hottest brand in the world,” Trump told the attorney general’s office during a deposition last year.

Since Judge Engoron’s order last month, Trump’s lawyers have made a concerted effort to delay the enforcement of the massive financial penalty in his civil fraud case as well as the $83.3 million judgment he was ordered to pay after a jury found him liable for defaming the writer E. Jean Carroll. Trump, who has denied all wrongdoing, has filed a notice of appeal in that case.

Following Trump’s fraud judgment, Trump’s lawyers first asked Judge Engoron to delay entering the judgment by 30 days “to allow for an orderly post-Judgment process, particularly given the magnitude of Judgment.”

Engoron denied that request and signed the judgment on Feb. 22; the following day, the New York Supreme Court clerk entered the judgment, effectively starting the clock for the financial penalties in the case.

“You have failed to explain, much less justify, any basis for a stay,” Engoron wrote in response to the defense’s request. “I am confident that the Appellate Division will protect your appellate rights.”

The following week, Trump’s lawyers asked New York’s Appellate Division, First Department for permission to post a $100 million bond — a fraction of the over $550 million needed to cover the full judgment. They advised the court that a bond for the complete judgment was “impossible” and that the Trump Organization might have to sell off properties.

“In the absence of a stay on the terms herein outlined, properties would likely need to be sold to raise capital under exigent circumstances, and there would be no way to recover any property sold following a successful appeal and no means to recover the resulting financial losses from the Attorney General,” defense attorneys said.

Lawyers for the New York attorney general pushed back against their request, arguing Trump might attempt to evade punishment if his appeal fails.

An appellate judge on Feb. 28 denied Trump’s request for a stay of the financial penalty, but lifted a ruling Judge Engoron handed down prohibiting Trump from running any New York company and accessing lines of credit, opening the door for Trump to ask surety companies for a bond.

But Trump’s lawyers returned to the same court last Monday, asking again for a delay because finding a bond company to sign off on a $550 million bond was a “practical impossibility,” they told the court. Because of the size of the bond and the necessity for Trump to use property as collateral, more than 30 surety companies turned down the potential bond, according to a court filing.

“Perhaps worst of all, the Attorney General argues that Defendants should be forced to dispose of iconic, multi-billion-dollar real-estate holdings in a ‘fire sale,'” a defense lawyer told the court.

Trump himself has claimed that he has almost $500 million dollars in cash, but his lawyers have argued that he can’t both pay the bond and run his companies. Despite not spending his own money on his presidential campaign in 2016, Trump also claimed he wanted to use the money on his current campaign.

“Billions of dollars of value, billions of dollars in properties, but they’d like to take the cash away, so I can’t use it on the campaign,” Trump said last week.

Trump’s lawyers also made a similar effort to delay the enforcement of the judgment in his $83.3 million defamation case, though the former president eventually secured a $91 million bond for the judgment plus interest by using a brokerage account as collateral.

It’s unclear if New York’s Appellate Division will make a ruling about Trump’s request for a delay — or his request for permission to appeal to a higher court — in time to impact the Monday deadline. If Trump does not secure a bond or pay the judgment, the New York attorney general told ABC News last month that she would ask the court to begin seizing Trump’s assets.

“If he does not have funds to pay off the judgment, then we will seek judgment enforcement mechanisms in court, and we will ask the judge to seize his assets,” James said about the process, which she could initiate on Monday.

While James won’t be putting a padlock on buildings like Trump Tower or 40 Wall Street, she took initial steps last week to potentially seize a golf course and estate that Trump owns in New York’s Westchester County by registering the judgment there.

“I’m going to assume they’re going to go to the New York properties first because that’s the easiest thing to do,” Steven Cohen, a New York attorney whose work includes enforcing judgments, told ABC News.

James could also opt to take further steps by issuing a subpoena for Trump’s financial information including tax returns, according to judgment enforcement attorney Peter Agulnick.

Regardless of the initial steps she takes, Trump’s lawyers are likely to fight every step of the way to slow the process of the asset seizure and potential auctioning of properties.

“That’s going to be a long process, and it’s not going to happen overnight,” trial attorney Kevin O’Brien told ABC News.

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