That’s the rub: that whole time everyone thought he was a business titan? He wasn’t really rich at all. Not only are real estate ventures heavily leverages to begin with, but he also ran his businesses into the ground by grifting money out of them. When the E. Jean Carroll verdict came in, there was a very real chance he would not have been able to meet it without significant pain.

However, since then, he found his Crypto religion, and then once he won the Presidency the second time, he has been inviting right foreign interests to bribe him through Crypto. So he is actually rich now, based solely on selling influence via meme tokens.

He literally faked it until he made it. And needed two tries to get it right. No wonder he also needs to grift his name into existing things.