What We Know About Trump’s Failure to Arrange a Half-Billion-Dollar Bond

It’s crunchtime for Donald J. Trump.

By Monday, March 25, the former president must secure an appeal bond for roughly half a billion dollars in his civil fraud case in New York, and his ability to do so was called into question this week.

In a court filing, Mr. Trump’s lawyers revealed that he had been unable to secure an appeal bond despite “diligent efforts” that included approaching about 30 bond companies.

While Mr. Trump this month managed to post a $91.6 million bond in his defamation case against the writer E. Jean Carroll, securing the deal at the 11th hour from a large insurance company, he lacks the assets needed to secure the far bigger guarantee for the fraud case.

If he cannot produce the bond in time, Mr. Trump faces the possibility of financial disaster and humiliation. New York’s attorney general, Letitia James, who brought the fraud case, would be entitled to collect the $454 million and could seek to seize Mr. Trump’s New York properties or freeze his bank accounts.

And Mr. Trump’s money problems spread well beyond New York. As the presumptive Republican nominee for president, he is facing increased pressure to raise money to fund his campaign, lagging behind his opponent, President Biden, in fund-raising.

In recent days, The New York Times has received many questions about Mr. Trump’s financial woes. Here are answers to several:

What was Trump accused of?

Ms. James took Mr. Trump, his company and his adult sons to trial last fall, accusing them of fraudulently inflating the value of his golf clubs, office buildings and other properties to the tune of about $2 billion.

Mr. Trump exaggerated the property values, and in turn his own net worth, to obtain favorable loan terms from banks and insurers, according to Ms. James.

At the trial, which lasted months, Ms. James’s lawyers showed that Mr. Trump’s company had ignored appraisals and manipulated numbers to sometimes absurd heights.

For example, the former president had valued his triplex apartment in Trump Tower on Fifth Avenue as if it were 30,000 square feet for years. It was actually 10,996 square feet.

Mr. Trump lost the trial. The judge overseeing the case — there was no jury — ruled in favor of Ms. James.

How was he punished?

The judge, Arthur F. Engoron, came down hard on Mr. Trump, imposing a judgment of $355 million plus interest, amounting to $454 million.

The judge also imposed a range of penalties that could curb Mr. Trump’s influence over his family business, barring him from serving as a top executive at a New York company for three years.

What comes next?

Mr. Trump has appealed the judgment.

Although he does not have to pay Ms. James’s office the $454 million while he appeals, he is on the hook to either cut a check to the New York State Court system for the full amount himself, or, more likely, obtain an appeal bond.

What is an appeal bond?

In this case, it would be a document in which a bond company promises to pay the $454 million judgment, plus interest, if Mr. Trump were to lose his appeal and fails to pay.

To obtain a bond of such size, Mr. Trump would need to pledge a significant amount of collateral to the bond company — about $557 million, his lawyers said — including as much cash as possible, as well as any stocks and bonds he could sell quickly.

He would also owe the bond company a fee that could amount to nearly $20 million.

Does he have enough cash to obtain one?

Short answer: No.

A recent New York Times analysis found that Mr. Trump had more than $350 million in cash as well as stocks and bonds, far short of the $557 million he would need to post in collateral.

In a court filing on Monday, Mr. Trump’s lawyers said they had contacted more than 30 bond companies, and none had agreed to do a deal.

But I thought he was a billionaire?

While Mr. Trump has long bragged about his wealth, his true financial position remains something of a mystery. And most of his wealth is tied up in his real estate holdings, which bond companies don’t typically accept as collateral.

He also has less liquid collateral available today than he did even a few weeks ago. Earlier this month, Mr. Trump had to post a $91.6 million bond in the defamation case he lost to E. Jean Carroll. For that, he most likely had to pledge more than $100 million in collateral to Chubb, the insurance company that provided the bond. That money cannot be used as collateral for a second bond.

What is the deadline for the bond?

Mr. Trump asked an appeals court either to pause the fraud judgment while he appeals it, or to accept a lesser bond of $100 million. The court could rule this week.

Although Ms. James could have moved to collect the $454 million immediately, she offered a 30-day grace period, which ends on March 25.

Ms. James could still grant additional time for Mr. Trump to pay or show mercy to the former president by offering a counterproposal.

What other options does Trump have?

If the appeals court denies his bid for a pause, and he still can’t find a bond by March 25, he might appeal to the state’s highest court.

Assuming that fails, he could quickly sell one of his properties or other assets, or seek help from a wealthy supporter. He might also try to obtain a loan from a bank, which he could then post as collateral for a bond.

And if all else fails, he could have the corporate entities implicated in the fraud case file for bankruptcy, which would automatically halt the judgment against those entities. But Mr. Trump is likely to balk at bankruptcy, and even if he were to pursue that path, it is not a panacea.

Ms. James’s judgment would not be halted against Mr. Trump himself, and she would most likely seek to hold him accountable for his company’s debts.

How could the state collect?

If Mr. Trump misses the March 25 deadline, Ms. James will be free to collect the money owed to the state.

It could get ugly for Mr. Trump.

Although Ms. James can’t put Mr. Trump in jail — because it is a civil case, not a criminal one — she still has plenty of leverage. With help from a local sheriff, she could freeze some of his bank accounts.

And if she wanted to take a more aggressive posture, she could even try to seize some of the properties involved in the case, including his office tower at 40 Wall Street in Lower Manhattan.

One swift option would be for her to place a lien on the buildings. Actually seizing them through the courts and the foreclosure process could take significant time.

Ms. James probably would not be entitled to seize assets unrelated to the case, though that and similar questions might require litigation to resolve.

Could Trump use campaign money to pay?

Probably not.

A super PAC supporting Mr. Trump’s candidacy can raise unlimited amounts of money, but it is legally banned from coordinating with him and cannot pay the judgment.

And although the former president has used a political action committee under his control to pay for lawyers and witnesses in his legal cases, that group lacks the kind of money needed to address the $454 million penalty.

He is now scrambling to raise campaign cash as he faces a significant financial deficit. Mr. Biden’s campaign recently announced that it had entered March with $155 million cash on hand. Mr. Trump’s campaign and the Republican National Committee had about $40 million total on hand at the end of January, though the Trump campaign has not released a more recent total.

What else is happening on March 25?

Mr. Trump also has a crucial hearing in his Manhattan criminal case, which could be the first prosecution of a former American president.

The Manhattan district attorney, Alvin Bragg, filed charges against Mr. Trump that accuse him of covering up a sex scandal involving a porn star to bolster his 2016 presidential campaign. The case is now proceeding to trial.

Jury selection was originally scheduled to start on March 25, but the trial was delayed late last week after the disclosure of more than 100,000 pages of records that had been in the possession of the federal prosecutors.

While the documents have now been turned over, Mr. Trump’s lawyers were given until mid-April to review the papers.

Justice Juan M. Merchan set the March 25 hearing to determine if the trial should be delayed further and to rule on Mr. Trump’s motion for an outright dismissal.

The Manhattan case is among four criminal prosecutions Mr. Trump faces.