How is Trump going to pay for E. Jean Carroll?

Trump’s Desperate Chess Move: The Billion-Dollar Dilemma and the Kushner Connection

The Donfather — a psychological and monetary collapse

CJ Sterling
8 min readJan 28, 2024


The King is Checkmated

The question on the board is, “How is Trump going to pay for the $83.3 million award in the E. Jean Carroll case?” Or, more accurately, who is going to pay it? Note that the $500,000 in pre-judgment interest adds to his looming debt, and the most recent Trump business fraud judgment totaled about $454 million.

Trump supporters have been paying for his legal fees since 2015, nearly ten years, thanks to loose rules from the Save America PAC and even looser regulatory oversight by the Federal Elections Commission. His MAGA PAC fund is getting low, and donations have dropped, especially over the E. Jean Carroll Case, which I wrote about recently. Since 2015 to July of 2023, his legal bills were $130 million. This last six months report another $50 million. His biggest supporter, the Koch Network, has abandoned him, along with many other large donors. This is not to say Trump is not raising millions, but as of the third quarter, Biden has far outpaced Mr. Trump.

My take in the previous article was that Trump was pouring gasoline on the fire because of his narcissistic rage toward E. Jean Carroll for embarassing and shaming him. Narx hate that, and they will go after their accusers.

But there is an angle I hadn’t considered before. It fits the mob-boss role Trump has held throughout his adult life. From 1979 to 2016, Trump and his businesses have been defendants in over 4,000 court cases.

Try this on for size: Trump is facing $88.6 million in defamation awards for the two E. Jean Carroll rape/defamation cases, plus a disgorgement amount in his New York business fraud trial totaling nearly $450 million.

The Carroll award has to be secured by a bond. That bond is not necessarily dollar-for-dollar, but not the 10% you might pay if your cousin needed to be bailed out of jail. And it must be relatively liquid — cash; bonds and/or collateral…



CJ Sterling

Writer, journalist. Commentary: Washington Post, Economist, Daily Beast, New York Times, Seattle Times, Crosscut, The Stranger. 2.9 million views, Quora.