By Michael R. Sisak | Associated Press

NEW YORK — Donald Trump is hurtling toward a critical deadline in his most costly legal battle to date. If the former president doesn’t come up with a financial guarantee by Monday, New York’s attorney general can start the process of collecting on the more than $454 million Trump owes the state in a civil fraud lawsuit.

Trump’s lawyers are trying to stop that from happening. They have asked a court to put collection efforts on hold while he appeals the verdict.

The presumptive Republican presidential nominee tried getting a bond for the full amount, which would have stopped the clock on collection during his appeal and ensured the state got its money if he were to lose.

But more than 30 underwriters said no, Trump’s lawyers told the court. They said getting a bond for such a large sum is “a practical impossibility.”

That’s raised the possibility that New York Attorney General Letitia James could start trying to enforce the judgment as soon as Monday.

Here’s a look at what that might look like, and what it would mean for Trump’s business empire.

COULD NEW YORK REALLY SEIZE TRUMP’S ASSETS?

Yes. If Trump isn’t able to pay, the state “could levy and sell his assets, lien his real property and garnish anyone who owes him money,” Syracuse University Law Professor Gregory Germain said.

Potential targets could include properties such as his Trump Tower penthouse, Wall Street office building and golf courses. James’ office could also seek court permission to drain Trump’s bank accounts and investment portfolios, or sell off other assets like his planes, helicopters — or even his golf carts.

Seizing assets is a common legal tactic when someone can’t access enough cash to pay a civil penalty.

In a famous example, O.J. Simpson’s Heisman Trophy was seized and sold at auction to cover part of a $33.5 million wrongful death judgment. More recently, a city commissioner in Miami, Florida, fought to keep his home after a federal judge ordered it seized and auctioned off to help pay a $63.5 million judgment in a political retaliation case.

New York state seized three large moving trucks in 1999 to help satisfy a $250,000 judgment against a moving company that ripped off customers. In 2006, the state seized a $342,000 investment account to cover part of a $2 million judgment against operators of illegal tire and solid waste dumps.

HOW SOON COULD IT HAPPEN?

Not quickly. Any attempt to collect would be done through the courts, including through liens and foreclosure actions.

State officials can’t just show up on Monday and padlock Trump Tower, but they can lay the groundwork by issuing subpoenas requiring Trump to provide information about his 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, a Democrat, said in a recent interview with ABC News.

WHY DOES TRUMP OWE THIS MONEY?

The state, through James’ office, sued Trump in 2022, alleging he had committed fraud for years by inflating his wealth on financial statements given to banks and insurance companies in connection with various business deals.

In February, after a 2½-month trial, Judge Arthur Engoron ordered Trump to pay $355 million plus interest, saying, “The frauds found here leap off the page and shock the conscience.”

Trump denies any attempt to deceive banks or anyone else about his wealth. He has said the judge’s decision and the lawsuit itself were politically motivated attempts to keep him from reclaiming the White House in 2024.

He has also argued that it is unfair to make him sell off assets or spend huge amounts buying a bond when the case is still being appealed, though a court requiring an appeal bond is fairly common in New York and other jurisdictions.

Asked Tuesday if he’s confident he can pay, Trump lashed out at what he deemed “a rigged trial by a crooked judge and a crooked attorney general.”

“We have a lot of cash and we have a great company, but they want to take it away or at least take the cash element away. Billions of dollars in 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 told reporters after voting in Florida’s Republican primary.

“We’ll see how the courts rule on it,” he said.

COULD TRUMP PAY IF HE WANTED?

Trump says he is worth several billion dollars, but much of his wealth is tied up in skyscrapers, golf courses and other properties.

He reported having about $294 million in cash or cash equivalents on his most recent publicly available financial statement, but that document is outdated, covering the fiscal year ending June 30, 2021. It’s also one of the documents that Engoron deemed fraudulent for exaggerating Trump’s wealth.

Since then, Trump has netted nearly $187 million from selling the lease on his Washington, D.C., hotel and the rights to manage a New York City golf course. His current cash position is unclear. During his civil fraud trial, he said he had more than $400 million in cash, but that figure is unverified.

Trump also has other legal bills. In January, a jury ordered him to pay $83.3 million for defaming writer E. Jean Carroll after she accused him of sexual assault. Earlier this month, Trump secured a $91.6 million bond to guarantee that judgment while he appeals.

Trump’s lawyers said freeing up cash by offloading some of Trump’s properties in a “fire sale” would result in massive, irrecoverable losses.

ARE THERE OTHER WAYS TRUMP COULD RAISE THE MONEY?

Trump could receive a financial windfall from a looming deal to put his social media company, Trump Media & Technology Group, on the stock market under the ticker symbol DJT.

A shareholder meeting is scheduled for Friday. If the deal is approved, Trump would own at least 58% of the shares in the company, which runs his Truth Social platform. Depending on share price, that could be worth several billion dollars, though he might not be able to turn those stocks into cash immediately.

In the meantime, the amount Trump owes is increasing by nearly $112,000 each day due to interest. As of Tuesday, he owed the state nearly $457 million.

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To obtain a bond, Trump’s lawyers said they would be required to post collateral covering 120% of the judgment.

Last month, Trump’s lawyers proposed posting a $100 million bond, but a judge in the state’s mid-level appeals court said he had to pay the full amount. Trump has appealed that decision.

COULD TRUMP DECLARE BANKRUPTCY?

Under federal bankruptcy law, enforcement of the judgment would be paused if he personally declared bankruptcy. However, he would still be personally liable if just his company, the Trump Organization, or other entities were to declare bankruptcy.

Trump has repeatedly bragged that he has never, personally, declared bankruptcy, although several of his previous companies have.

“If he can’t post a bond or meet the appellate division’s bonding requirements, then I would expect him to file bankruptcy to take advantage of the automatic stay on collection,” law professor Germain said.

“But that’s a couple of chess moves away, so we will just have to see what happens.”

Associated Press reporter Jill Colvin in New York contributed to this report.