Chubb was the only company willing to even try and negotiate that, and Trump couldn’t come up with a satisfactory package for them.
I’m seeing possibly subtext here that Chubb intentionally screwed Trump which was a surprise.
So Team Trump were talking with Chubb for bonds against both the $91 million judgment as well as the $464 million judgment. Team Trump was offering up both liquid assets (the Schwab brokerage account with whatever stocks and bonds are in there) and real estate. Team Trump really wanted bonds against the real estate.
It looks like Chubb said something like “Hmm, well we have two bonds we’re talking about here. Lets do the $91 million bond in purely liquid, and then we can look at the real estate for the $464 million bond. Seeing how you need the $91 million bond in a couple of days lets get that knocked out first”. Team Trump agreed handing over all the liquid assets (the Schwab account) so the $91 million bond is now “fully collateralize” meaning liquid money to back up the bond.
Then Team Trump says “Okay the $91 million bond worked great! Now lets do the $464 million bond backed by Trump real estate!”
Chubb says “Hard pass, not interested.”
So all the good stuff is gone and Trump has nothing good left to try to secure any bond on the $464 million. Chubb makes whatever commission they placed on top of the $91m bond, and simply pays out the $91m to Jean Carrol when the appeal fails. Jean Carrol wins, Chubb wins, Trump gets played.
I say all of this with zero love for Chubb, but when a grifter gets grifted, its satisfying to watch.