2. Evander Holyfield
Record: 44-10-2 (29 KOs)
Former Undisputed Cruiserweight and Heavyweight Champion
Estimated Career Earnings: $250 million
Two of the fastest ways for any athlete to blow millions of dollars is having lots of kids by many different women and going through multiple divorces. This lethal one-two combo put a hurting on Holyfield’s pockets to the tune of nine figures and have forced the boxer to continue his career as he pushes 50. In the summer of 2008, Holyfield’s $10 million mega mansion (109 rooms and 17 bathrooms, really fam?) went into foreclosure. Despite these financial troubles, Holyfield remains adamant about giving to the church. According to his third wife, an argument over paying tithes is the reason behind him allegedly assaulting her last year.