One of the most ridiculous false pretenses Trump tries to maintain is that he can only pay with a single, $454M bond, and since he can’t get one that large, he should, obviously, just be forgiven the amount entirely and let off the hook.
What he doesn’t want anyone to know is that, obviously, he could just get several smaller bonds for, say, $50M or $75M or $100M until it added up to the $454M or however much he needs to post for the appeal. In fact, he even tried to offer a $100 bond before, but used it instead in the E Jean Carrol appeal.
Like literally chubb dogded a bullet lending this money earlier rather than having to be available for the next big payout.
If you ask me is a small price to pay for salvation
Chubb did a fully collateralized bond. Meaning they got something of actual value, not just trump's word. In this case a Schawb brokerage account full of stocks and bonds for (I believe) more than the value of the bond. Plus Chubb probably added a fee on top of the value of the bond to service the transaction. When trump loses the E Jean Carroll appeal, Chubb will hand over cash and sell off the assets in the Schawb account and pocket their service fee.
Why would they do it this way instead of just directly selling what's in the account? I get that it takes time to unwind stuff like that, but surely it can be done in the time the judge gave?
Taxes. If by some stroke of miracle he wins the appeal, he won't have to pay capital gains taxes that he otherwise would have had to pay if the portfolio was liquidated.
This. And to put numbers on it, long term cap gains taxes (for things in the account held for 2 years or more) is 20%. For short term (things in the account owned for less that 2 years) it can be as 37%. So if the account is just used as collateral, and Chubb charged a fee of less than 20% then the bond is a cheaper way to get the money for the appeal.