New York juries have found, by a preponderance of the evidence, that former President Donald Trump sexually assaulted writer E. Jean Carroll in a Bergdorf Goodman dressing room in the mid-90s and then repeatedly defamed her, falsely accusing Carroll of lying about the incident. “It’s a total false accusation,” Trump said in June 2019. “I don’t know anything about her. She’s made this charge against others, and you know, people have to be careful, because they are playing with very dangerous territory.” 

On January 26, 2024, a jury found that Trump "acted maliciously, out of hatred, ill will, or spite, vindictively, or in wonton, reckless, or willful disregard of Ms. Carroll's rights." The jury awarded Carroll $83.3 million in compensatory and punitive damages — money intended to compensate for the damage Trump inflicted on her reputation and deter Trump from similar conduct in the future. (That comes on top of a $5 million verdict, based only on statements about Carroll that Trump made after leaving the White House, awarded by a separate jury last May.) 

Trump is appealing the both verdicts. But the jury award for the January case becomes final today, meaning that Trump owes Carroll the $83.3 million. Trump's attorneys tried asking the judge overseeing the case, Lewis Kaplan, to put the judgment on hold while he pursued the appeal, but Kaplan refused. That left Trump with two options: place 110% of the judgment in a court-controlled account ($91.6 million) or secure a bond for the same amount by a reputable third party. (The additional amount is required because, if the judgment is upheld on appeal, Trump will also owe Carroll interest.)

To secure a bond from a surety company, you generally need to do two things: 1. Pay a fee, usually about 2% of the verdict, and 2. Show the company that you have unencumbered assets to cover the judgment should your appeal be unsuccessful. 

On Friday, Trump presented a bond from the Federal Insurance Company, a subsidiary of Chubb. 

Judge Kaplan will decide whether or not to accept the bond today. It does have some unusual conditions. The terms of the bond gives Chubb up to 60 days after an appellate ruling in Carroll's favor to satisfy the judgment if Trump fails to pay. Carroll's attorney has until 11 AM today to decide whether to object. 

Trump and Chubb have a history. In 2018, Trump appointed Chubb's CEO, Evan Greenberg, to a White House advisory council on trade policy. In April 2020, Greenberg was named by Trump to a counsel of business leaders advising the president on how to reopen the economy after the onset of the coronavirus pandemic. After the events of January 6, 2021, Greenberg issued a statement defending the integrity of the election. But the statement did not explicitly name Trump. "We look to all of our elected leaders from both parties to set an example by their respect and active support for the orderly transfer of power and their condemnation of false claims of election fraud," Greenberg said. 

Chubb also played a role in a separate civil case against Trump, brought by New York Attorney General Letitia James, for financial fraud. According to James, Chubb allowed Trump to cut corners. In 2010, prosecutors alleged, "Chubb sent an insurance appraiser to determine the worth of Trump’s triplex penthouse apartment at Trump Tower, but that Trump rushed the expert out of the premises within 15 minutes before the assessor could take any measurements." The appraiser was not allowed to see the primary bedroom because Trump told them that his wife, Melania, was sleeping. Trump then inflated the value of the apartment by claiming it was three times its actual size. On the basis of that and other fraudulent conduct, a judge imposed a $464 million judgment against Trump and his companies. 

Almost nothing is known about the terms of the $91.6 million bond agreement between Trump and Chubb. And Chubb is refusing to provide any details. "As a matter of policy, we do not comment on client-specific information," Chubb said in a statement. 

In most cases, the specific terms of a bond are irrelevant. The court is only interested in ensuring that the judgment, if upheld, will be satisfied. But this is not an ordinary case. Trump is the presumptive presidential nominee for the Republican Party and, potentially, the next president. The public has an interest in knowing the financial entanglements of a prospective president. That is why candidates for president are required to file financial disclosure reports. (Those disclosure reports, however, only require candidates to list their assets and liabilities in broad strokes and do not require Trump to disclose the details of his bond.)

It's possible that Trump produced the unencumbered assets himself to secure the bond. But Trump is facing a cash crunch, and may not be able to (or want to) set aside $91.6 million in unencumbered assets for this purpose. Trump has numerous mortgages coming due and has to somehow obtain a bond for the $464 million New York fraud verdict by the end of the month. That raises the possibility that the structure of the bond could make Trump financially reliant on other people or entities, including those with a vested interest in the policies of the next president.  

"The issue is: is [Trump] going to be beholden to somebody," former US Attorney and General Counsel of the FBI Andrew Weissmann said. "We already know that somehow he got a bond from Chubb. I'm interested in knowing, for instance, did somebody have to co-sign?" 

A third defamation case?

Trump is facing more than $500 million in civil judgments but seems determined to add to the total. At a rally in Georgia on Saturday night, Trump repeated the same claims about Carroll that just resulted in a $83 million jury verdict earlier this year. 

Sometimes it's not good to be rich. I just posted a 91 million dollar bond. 91 million. On a fake story. Totally made up story. Think of it. 91 million. I could say things about what it would cost normally. 91 million. Based on false accusations made about me by a woman that I knew nothing about. Didn't know. Never heard of. I know nothing about her. She wrote a book. She said things. And when I denied it I said, "It's so crazy. It's false." I got sued for defamation. That's where it starts… The woman didn't even know when it happened. And she admitted on Anderson Cooper, she said, "I think it was sexy." Can you believe this. 91 million.

Carroll has said that she would absolutely sue Trump again if he continued to defame her.