For a guy who likes to talk so much, I notice even early in his career, Donald Trump never actually gave any insights into the financial details of his real estate empire. In the early 1990s, many Trump properties were overextended, like the Plaza Hotel and Atlantic City casinos, and declared bankruptcy. Ever since then, it’s been a game of speculation just how much money Trump really has. One has to try to read what few clues there may be.

In order to appeal the civil trials he just lost, Trump must come up with something around $500 million for the supersedeas bonds. Last week he was able to appeal the E. Jean Carroll case, securing a surety bond from Chubb Group.

This suggests Trump is in good shape financially and legally. I believe an insurance company will also step in for the second, larger Letitia James case as well. Chubb would not have jumped in for the one, unless they believed there are enough Trump assets to cover both. That’s basic underwriting. They don’t want to guarantee one part of the Trump holdings, while another interconnected part is going down in flames.

Just my hunch also, but I would think there might be a whole syndicate of insurance companies trying to assist with Trump’s money issues for a while. They don’t want his empire liquidated and a subsequent fire sale loss by his lenders; they want to be as helpful as possible in financing his appeals.

And those appeals themselves hit at the heart of what drives insurance companies nuts these days—crazy trial court verdicts that award millions of dollars in unwarranted damages. Insurance company lawyers must have looked at what happened and thought the judgments against Trump will either be reduced or thrown out on appeal and might also produce some powerful precedents for their side in the Supreme Court, as an added bonus.

Consider, in the federal E. Jean Carroll case, she was awarded $65 million in punitive damages alone and a total dollar figure eight times higher than initially sought in her lawsuit. An astounding figure, given the 80-year old Carroll says Trump’s comments only cost her a $60k a year job at Elle.

The U.S. Supreme Court has long been trying to reign in such jury awards with cases like State Farm that limit punitive damages to a low multiple of actual damages.

State Farm is also why I think the recent outrage in the Mark Steyn/Michael Mann defamation suit will be reversed. Mann was awarded a mere $1 in actual damages yet given $1 million in punitive damages. That’s insane. Traditionally in American law, punitive damages is three times the actual damages, not one million times!

None of this seems to have even been on the mind of Judge Engoron in New York, who awarded Letitia James $355 million on a theory of unjust profit “disgorgement”,  even though there were no victims and no losses among Trump’s lenders. Disgorgement is also a key doctrine the Supreme Court has lately been skeptical about. It was at the center of the recent Lieu v. SEC, where the court by an 8-1 decision wanted to see some real damages to victims before disgorgement was ordered.

The plaintiff’s bar is none too happy about the recent pro-insurance SCOTUS victories and is fighting back. However, when you consider how flimsy the claims for damages are for E. Jean Carroll and Letitia James, Big Insurance must be just licking their chops at the kind of decisive appeals court opinions to be had, against what is sometimes called “jackpot justice”. Even the notorious Democrats who own insurance companies, like Warren Buffet, may be quietly rooting for Trump on this.

This is all very good news for Trump. My experience in business and politics has always been—if you want to find the winning side, just look at where the insurance guys are lining up.

Frank Friday is an attorney in Louisville, KY

Image: Gage Skidmore from Peoria, AZ, United States of America, CC BY-SA 2.0, via Wikimedia Commons, unaltered.