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Michael M. Santiago

<a href="https://www.washingtonpost.com/donald-trump/" target="_blank" class="contextual_link">Donald Trump</a>, who lost a civil fraud case in New York last month, must put up a bond of nearly half-a-billion dollars if he wants to stop New York Attorney General Letitia James (D) from collecting while he appeals. James is poised to begin claiming his assets if he fails to put up the bond by Monday.

In February, Judge Arthur F. Engoron <a href="https://www.washingtonpost.com/politics/2024/02/16/judge-engoron-ruling-trump-ny-civil-fraud-trial/" target="_blank">ruled </a>that Trump, his two eldest sons and two of his executives submitted false data to lenders and insurance companies to secure better deals. Engoron ordered Trump and his co-defendants to pay $464 million, an amount that continues to grow at a rate of more than $100,000 per day. In the weeks since that judgment, the former president’s options have dwindled.

Trump’s attorneys have asked appellate judges to reduce, delay or waive the bond requirement. The appeals court has yet to reach a final decision.

His lawyers <a href="https://www.washingtonpost.com/politics/2024/03/18/trump-civil-fraud-judgment-bond-450-million/" target=_blank>told </a>an appellate court that they tried to get a bond through 30 different insurance companies but none offered one because they would not accept real estate — which accounts for most of Trump’s wealth — as collateral. Selling golf courses or hotels generally takes much longer than a few days or weeks, time he no longer has.

Trump, who has raged against Engoron’s decision and James on social media, is now down to a handful of mostly unpalatable outcomes. Here are the scenarios experts say could be the most likely to play out over coming days.

The appeals court generally issues rulings on Tuesdays and Thursdays, so there is very little chance it will act by Monday on Trump’s request to waive the bond requirement. If it doesn’t, and if Trump doesn’t post a bond by then, legal experts say there is nothing preventing James from calling on the New York City sheriffs or on city marshals to begin seizing his assets.

But there are reasons for her to wait. Legal experts say Trump has a chance of getting some type of relief from the appeals court. If James begins moving on his assets before the court rules, she may have to backtrack afterward. She also may consider the optics of moving quickly. As Nikos Passas, a Northeastern University criminology professor, put it: “She doesn’t want to be accused of being overly aggressive and unfair.”

James has said she intends to take Trump’s assets if he fails to pay. “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,” she <a href="https://abcnews.go.com/US/letitia-james-shes-prepared-seize-trumps-assets-pay/story?id=107381482" target=_blank>told</a> ABC News last month. In the interview, James mentioned Trump’s 40 Wall Street office building by name.

Experts say James would probably start with New York properties, partly because the LLCs that own two of them — 40 Wall Street and his Seven Springs estate in Westchester County — are defendants in the fraud case. James’s office already filed Engoron’s judgment with a court in Westchester County, a first step toward seizing the Seven Springs property, as CNN first <a href="https://www.cnn.com/2024/03/21/politics/trump-calls-ny-attorney-generals-bond-suggestions-impractical-and-unjust/index.html" target=_blank>reported</a>.

“Once she has that judgment lien, what she can do is foreclose on that judgment lien and essentially mandate a sale of the properties to satisfy the judgment,” said Stewart Sterk, a professor of property and real estate law at Cardozo School of Law.

James could decide to move against Trump on multiple fronts, which would make for an unprecedented showdown with the GOP nominee for president. She could start by issuing a subpoena to learn more about what assets he has and where they are located, but she may not need to since she already knows — from information surfaced in the fraud case — where much of his wealth resides. New York City marshals could go to Trump’s banks and drain his accounts at her behest, said Adam Pollock, an attorney who formerly served as assistant attorney general in New York. Pollock said she could also begin <a href="https://law.justia.com/codes/new-york/2022/cvp/article-52/5236/" target=_blank>scheduling auctions</a> of his properties in New York or filing liens against his properties in other states, a step toward acquiring them as well. To get the full amount, she may need to take more than one or two properties, and she would get to choose which ones to go after.

Trump could find a well-to-do person (or several people) to come to his aid and lend him money to put up a bond. A person with Trump’s wealth would normally be able to work with a bank, which is used to taking real estate as collateral, to get a bond issued. But Trump has few banking relationships remaining, records show, and limited access to banks makes getting a bond much more difficult.

The parent company of Trump’s social media platform, Truth Social, is going public following <a href="https://www.washingtonpost.com/technology/2024/03/22/trump-mediamerger-vote/" target=_blank>investor approval</a> Friday. His stake in the company, at Friday afternoon’s share prices, is worth about $3 billion. A lockup agreement forbids him from selling his shares for six months. He could ask members of the company board — many of them close allies — to waive that provision so he can sell shares, but experts said doing so would risk driving the stock price down. Trump could also explore borrowing against his shares to put up the bond, but that too could be complicated by the lockup provision.

In a post on Truth Social on Friday, Trump wrote that he has “almost five hundred million dollars in cash” as he attacked Engoron and his judgment in the fraud case. Experts said that statement seemed to undercut Trump’s lawyers’ argument that he didn’t have enough cash to secure a bond. Trump’s lawyer, Christopher Kise, sent a statement in response to a request from The Washington Post: “What he’s talking about is the money (reported on his campaign disclosure forms) that he’s built up through years of owning and managing successful businesses around the world. That is the very cash that Letitia James and the Democrats are targeting,” Kise said.

If Trump does put up a bond, a court-appointed monitor of his business empire and finances should have insight into that deal. This week, Engoron ordered that the monitor, former federal judge Barbara Jones, should be informed in advance of any efforts to secure bonds, including “any representations made by Trump Organization in connection with securing such bonds, any personal guarantees made by any of the Defendants, and any obligations of the Trump Organization required by the” bonding company.

The easiest way out of this predicament for Trump is to get a lifeline from the New York Supreme Court Appellate Division. Trump’s attorneys have asked that court to reduce, delay or waive the bond requirement. The court could say that Trump does not need to post a bond at all unless until his appeal is over and he loses, or the panel could allow him to post a smaller bond. Trump’s lawyers recently asked an emergency appeals judge to allow them to post a $100 million bond but the judge <a href="https://www.washingtonpost.com/politics/2024/02/28/trump-new-york-supreme-court-judgment-appeal/" target=_blank>denied </a>the request. A full panel is now reconsidering and could rule anytime.

Sterk, the professor, said that the court could grant Trump’s request to stop James from seizing assets until after he has a chance to appeal Engoron’s underlying judgment. If James seizes and sells Trump’s properties now, Sterk said, “he’s not going to be able to get them back.” If Trump were to eventually win his appeal, the sale of his properties couldn’t be undone. Appeals courts have to consider whether consequences of their rulings can be irreversible.

Trump’s attorneys have already signaled that if the state appellate division doesn’t stop James from seizing assets, they would take their request to the Court of Appeals, the state’s highest court. They need permission from the appellate division to do so.

As The Post <a href="https://www.washingtonpost.com/politics/2024/03/20/trump-bond-bankruptcy/" target=_blank>detailed</a> recently, legal experts — and some people in Trump’s camp — recognize that filing for bankruptcy would probably push all these problems down the road by months or maybe years. Trump wouldn’t escape his debt to the court — and in fact interest would still continue to accrue — but the clock would stop ticking on his need to immediately put up a bond. New York would have to get in line with other creditors and ask a bankruptcy judge to get paid.

Filing for bankruptcy could come at a political cost for a candidate who has marketed himself as a savvy businessman. People close to Trump told The Post this week that he is not considering it. But he has done it before. And he only has so many options left.

University of Wisconsin-Madison

Jonathan O'Connell is a reporter focused on investigations. He has covered economic development, commercial real estate and President Donald Trump's business. He joined The Post in 2010.

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Columbia University Graduate School of Journalism, MS

Montclair State University, BA in History

Shayna Jacobs is a federal courts and law enforcement reporter on the national security team at The Washington Post, where she covers the Southern and Eastern districts of New York. 

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Finalist for the Livingston Award in 2022. Member of the "Pegasus Project" team that won a George Polk Award in 2021. 

University of Florida

Drew Harwell is a reporter for The Washington Post covering technology. He was a member of an international reporting team that won a George Polk Award in 2021.

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