Yeah he personally isn’t broke and no matter how much debt Twitter racks up, it can’t put him in the red. That’s just how corporations work.
Still, he borrowed that $44bil and will have to face the people who lent it to him. Apparent the service on that debt is already equal to Twitter’s total operating expenses. That’s real money.
WhY he’s lost by this is prestige. He lost the court case and demonstrably got taken to the cleaners. He hasn’t been able to turn the business around and in fact has made it worse. And his creditors are left holding the bag. That’s some real humiliation for someone like him.