He filed for Chapter 11. This is not the same type of bankruptcy your broke uncles have had to file.
He's saying his liquid cash is 4.4mil, therefore he cannot pay the lady 5 (she is also requesting like 15 mil or so in punitive damages). The rest of his many many millions are tied up in companies that he owns or partially owns, stocks, bonds, trusts etc... This is all a strategic move on his part in hopes of reducing the amount of money he is going to have to pay.
His court case is against 50 cent the PERSON, not 50 cent the ENTERPRISE. Businesses and people are viewed separately in the courts.
He is gaming the system, and doing a good ass job of it. Props 50