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Trump's $540 million court fine tests his 'King of Debt' title

Erik Larson, Bloomberg News on

Published in News & Features

Donald Trump dubbed himself the “King of Debt” when boasting about how his business empire survived hard times, but a pair of big trial court losses this year are putting that moniker to the test.

The former president owes about $540 million from two recent verdicts, a number that exceeds even some of the biggest loans he’s taken out for his real estate empire. Trump is now a so-called judgment debtor, leaving him few options for avoiding or delaying those payments while he challenges them in court.

Before any appeal can proceed, courts generally require trial losers to post what’s known as a supersedeas bond equal to about 110% of a judgment. A judge could set the amount lower or higher. But Trump may have to commit almost $600 million in cash and other collateral for months or longer — if he can find someone willing to arrange such a bond.

That squeeze on Trump’s assets illustrates the financial risk of his mounting legal troubles — including four pending criminal prosecutions — as he campaigns to return to the White House. The Republican frontrunner is using donations from supporters to pay his legal bills, but the damage awards to writer E. Jean Carroll in a defamation trial and to New York state in a civil fraud trial are personal expenses he’ll have to cover on his own.

Numerous surety companies offering supersedeas bonds could work with Trump, and the collateral they get means the risk is generally low. While they prefer holding cash, they also accept what’s known as an irrevocable letter of credit, or ILOC, from a bank that would guarantee the bonds get paid if Trump loses his appeals. The banks would hold collateral that could include cash, real estate and other assets, while charging the debtor a fee of about 2%.

However, Trump’s relationship with banks has been somewhat fraught. Most offer ILOCs for a variety of reasons, and Trump may turn to lenders he’s worked with before, including Ladder Capital, Amboy Bank and Bryn Mawr Trust and Professional Bank, which has been acquired by Seacoast National Bank in South Florida. It’s unclear if all the lenders provide ILOC services, and terms of such agreements wouldn’t necessarily be made public.


If a debtor has additional legal troubles or a history of bankruptcies, that “can have an impact on such negotiations” and “make it much more difficult” to get a bond, said Zach Mefford, who co-founded ZipBond in 2021. “Every single surety bond is going to be underwritten on a case by case basis where the financial situation of that person is considered.”

One option for Trump to avoid a supersedeas bond is to post cash with the court instead. When Carroll won a $5 million civil judgment in her sexual-assault trial against Trump last year, he received permission to post 110% in cash with the court, which is holding it in escrow while he appeals. But the sheer size of the new judgments against him makes that route less likely.

“The courts do not want to act as a bank, and it is far simpler for them to accept a bond,” said N. Alex Hanley, the chief executive officer of Jurisco Inc., which offers them in all 50 states.

Trump’s predicament is shining a light on the niche industry for appeal bonds. Hanley describes them as “a good-faith requirement that the appellant is not simply delaying the payment.” Trump’s bond would be unusually large, as well as costly if his court challenges take months or longer, Hanley said.


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