Trump’s Options Dwindle as $454 Million Judgment Bears Down on Him

Monday is judgment day for former President Donald J. Trump — the day he fears a $454 million judgment against him might come due.

Hoping to stave off a financial crisis, Mr. Trump is racing the clock to block the New York attorney general from collecting the monetary penalty imposed in a civil fraud case. The attorney general, Letitia James, who brought the case accusing the former president of fraudulently inflating his net worth, has the power to freeze many of his bank accounts and begin the long, complicated process of seizing some of his properties.

Under New York law, Ms. James could have enforced the $454 million judgment once it became final last month, but she provided Mr. Trump a 30-day grace period that expires on Monday. Although Ms. James could move to collect at any moment, she is not expected to take any aggressive action Monday.

When Ms. James does act, her efforts, depending on their severity, could starve Mr. Trump’s family business of cash and drop the curtain on his final act as a New York mogul. And while Mr. Trump can seek to delay or limit some damage, that legal process is “slow torture,” said Mark Zauderer, a veteran New York business litigator who has handled many judgments.

“There’s nothing here for Trump to gain,” added Mr. Zauderer, who is a partner at the firm Dorf Nelson & Zauderer. “It’s just a question of how much he will lose and how long it will take.”

To avoid a humiliating outcome, Mr. Trump must find a company willing, for a fee, to post a half-billion dollar bond on his behalf, promising that it will cover the judgment if he loses a pending appeal and fails to pay. A bond of that size would have strings attached: Mr. Trump would need to pledge more than $550 million in collateral to the company, including as much cash as possible.