Evander Holyfield

Surely, fans will best remember Evander Holyfield as the undisputed champion at cruiserweight back in the late 1980s and heavyweight in the 1990s. Although decades had passed since he conquered the boxing world, the 58-year-old personality still got credit for being the only boxer in history who won the undisputed championships in two weight classes. He retired in 2014 and ranked 77th among the 100 greatest boxers in the history of The Ring, and in 2002 named him the 22 greatest boxers of the past 80 years.

At the time, Holyfield was at the peak of his career, earning a staggering $240 million worth of prize money alone. He had a lot of accolades and winnings until his lavish spending took the very best of him. Holyfield also had issues paying child support. His financial woes also forced him to lose his $10-million Georgia mansion and medals. Now, his net worth is only $1 million.