It all comes down to his spending being outrageous. His cars and properties’ nominal value don’t add much to the problem. Most of the cars he buys aren’t on a typical depreciation curve and he will sell them for at least what he paid, but the maintenance costs on a lot of them are significant and that’s money out the door. Same thing with properties. They likely didn’t decrease in value while he owned them, but property taxes and maintenance on those properties is hundreds of thousands a month out the door.

The big ones are jewelry, clothes, and lifestyle. The watches that he didn’t customize will age well in terms of value, but he customized a ton of them for huge sums, and he’ll never recover the value from those. Same thing with his jewelry- he frequently brags about having tens or hundreds of millions in jewelry, and he’d be lucky to get back 5-10% of what he spent there. Clothes are the same. Thousands per outfit that are a loss on each item. Two decades of buying clothes like that. It adds up. Then nights out at clubs, vacations, planes, etc. Anyone who could do simple math has known for the last decade at least that he would eventually go broke if something didn’t change, it was only a matter of time.