What are you saying he did?
From my understanding, she demanded $50M or she's going to sue. Based on a reported $100M deal with ESPN.
He offered her X, (whether that was $5M, $10M it was significantly smaller than $50M). She said, nah, I want $50M. He then said no and left the bargaining table.......
She goes public and sues. His reputation is fucked, again AND within 6 months of the last sexual incident.
His $100M deal is now severely affected......
He then settles, for allegedly $23M.
He is then FIRED, deal gone!!
If he had negotiated in good faith before the lawsuit went public..... "hey look, i know you probably heard about that deal. Its not signed, I do not have $100m. I could probably come up with $20M. Will that work? If this goes public there is NO MONEY. I'm going to lose that deal and then i cannot pay you anything. "
Once the lawsuit went public his fate was sealed.
He paid her $23M, allegedly and what did he gain?
His rep is still fucked and now he's tangentially unemployed. He lost all the way around.
But my more basic point was..... he couldve got all his freaky needs met with a better looking, more compliant check that would've kept her mouth closed.