21. Andre Rison
A Super Bowl winner with the Green Bay Packers, Rison had an outstanding career. However, he also loved the good life a bit too much. He spent over one million dollars on jewelry and millions more on flashy cars. Unfortunately, he experienced a culture of constant one-upmanship that affected a lot of players very badly. Terrible spending habits combined with maternity suits resulted in him going bankrupt.
He used to bring tens of thousands of dollars in his pockets to nightclubs just to show off and buy the most expensive bottles. But of course, this wasn’t sustainable. Overdue child support debts were the straw that broke the camel’s back. Furthermore, he admitted that he had no understanding of how taxes worked or anything to do with daily expenses. Finally, he lost around $20 million.