Mike Tyson | Est. $10 Million

Hailed by ESPN as “The Hardest Hitter in Heavyweight History,” Mike Tyson is one of the world’s most famous boxers. However, he is also controversial one. Back in his heyday during the late ’80s and ’90s, he was the youngest champion in history at age 20 and one of the highest-paid athletes. Tyson retired from professional boxing in 2006 and has ventured into doing advertisements and television appearances.

Today, his net worth stands at $10 million. However, if not for his impractical money management, he could have had $300 million. During the prime of his career, Tyson was notorious for living a lavish lifestyle and for spending millions on cars, jewelry, mansions, and more. Aside from spending his money on excessively luxurious life, he also divorced twice and paid highly for this. In 1992, he was convicted of raping, which is inevitable to decrease his wealth again. In 2003, he finally come to bankruptcy. He was able to bounce back, though it must have been quite a difficult lesson to learn.