I guess its hard to understand how a rich person to grow "broke", but I've been around a ton of millions and entertainers and athletes, and have a lot of friends in the industry, and there are two problems here:
One - entertainers are never paid like the athletes, unless you like Beyonce or something. Their money is usually really funny, becuase its cashed out, spent crazily and always tied to stipulations.
Two - You can have $10 mil, and I can wipe that away from you in a month. You got 3 houses, your momma got a crib, you got a condo in Miami, and you paying for flights etc etc, your monthly bills are skyrocketed and you dont even notice it. I aint nowhere near paid like these dudes, and in the industry Im in and the way I get paid, them $$$s creep up on me as well, and its crazy.
Lil Wayne wouldn't be oweing everybody in the world if he had it. It sucks, but its true.