IMO Jerry wants to win more than ever. It just has to be on his terms. He would rather lose doing it his way than letting someone else do it for him.
He doesn't really want to win or he would stop this "dressing up and playing pretend" game he's been playing as if he's a football man.
It was one thing when he was doing it in the '90s. You could forgive him for not realizing the reality of it after he'd accidentally stumbled onto some success. He was thrashing around, making a big show of trying to win, and you could credibly claim that he sure wanted to win but he just hadn't had enough evidence yet to convince him he was bad at this. That he was now the major obstacle to us winning.
But after decades of failure now, he's got enough data to realize the team is limited by his own inabilities.
He didn't want to be wrong about Jason Garrett, but after a decade, hefinally decided he had too much evidence that it wasn't working out. Why was 10 years of failure enough to move him in that case but 24 years of failure isn't enough to move him in this case?
It's because he fundamentally doesn't consider it failure for him to oversee the team not winning. Because he doesn't particularly care if we win or lose.
Sure, it'd be *nice* to win if he blindly stumbles into it again. But he's just as happy with us not winning. His actions prove this.