What Happens If Trump Can’t Get a Half-Billion-Dollar Bond?

It’s crunchtime for Donald J. Trump.

In six days, the former president must secure an appeal bond for roughly half a billion dollars in his civil fraud case in New York, a possibility that was called into question on Monday.

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 by March 25, Mr. Trump faces the possibility of financial disaster and humiliation. New York’s attorney general, 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.

Here’s what we know about Mr. Trump’s financial problems:

Why does Mr. Trump owe so much?

Attorney General Letitia James took Mr. Trump to trial last fall and accused him of fraudulently inflating the value of his assets to obtain favorable loan terms.

Mr. Trump lost, and Justice Arthur F. Engoron imposed a judgment of $355 million plus interest, amounting to $454 million. Although Ms. James could have moved to collect immediately, she offered a 30-day grace period, which ends on March 25.

Mr. Trump is now on the hook for the entirety of the judgment while he appeals. He can either come up with the money himself or, more likely, obtain a bond from a company that would promise to pay if Mr. Trump lost his appeal and defaulted.

For a bond of this size, Mr. Trump would need to pledge a significant amount of collateral — as much as $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 $20 million.

Does he have the money to cover it?

Short answer: no.

While Mr. Trump has long bragged about his wealth, his true financial position remains something of a mystery. A recent New York Times analysis found that Mr. Trump had more than $350 million in cash, but most of his other money was tied up in his real estate holdings.

In other words, he is not liquid enough to offer the collateral required for a bond this big.

And he has less cash available today than he did even a week ago. Mr. Trump had to post a $91.6 million bond in the defamation case he lost to E. Jean Carroll. To secure the bond, Mr. Trump most likely had to pledge more than $100 million in collateral to Chubb, the giant insurance company that provided the bond.

What comes next?

Mr. Trump has appealed the $454 million judgment and asked a higher New York court either to pause it or to accept a lesser bond of $100 million. Ms. James could also grant additional time for Mr. Trump to pay or show mercy to the former president by offering a counterproposal.

He might appeal to the state’s highest court, quickly sell an asset or seek help from a wealthy supporter.

And if all else fails, as a last resort, 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 a bankruptcy filing.

If none of these options happens by March 25, and Mr. Trump misses the deadline, Ms. James would be free to collect the money owed to the state.

Could he use campaign money to pay Ms. James?

Probably not.

A super PAC supporting his candidacy can raise unlimited amounts but 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 disparity with his election opponent, Mr. Biden. Mr. Biden’s campaign recently announced that it had entered March with $155 million cash on hand. While the Trump operation has not released a more recent total, between his campaign account and the Republican National Committee, there was about $40 million at the end of January.

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, the trial was postponed to mid-April to give Mr. Trump’s lawyers time 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.