Mike Tyson

Between his professional debut in 1985 at the age of 18 until his retirement two decades later, boxing legend “Iron” Mike Tyson made somewhere between $300 to $400 million. During the height of his career, a single fight was worth $30 million. But during that time, Tyson bought mansions, cars and Bengal tigers. In 2003, Tyson walked into a Las Vegas jewelry store and bought a $174,000 gold chain with 80 carats in diamonds.

Just 8 months later, he had to file for bankruptcy. The New York Times reported that he was $23 million in debt, owing the U.S. government as well as the British government about $17 million in taxes, three-quarters of a million dollars to seven law firms and $300,000 for limo services.

Tyson later appeared in the hit comedy “The Hangover” which parodied his high-flying lifestyle. But the former champ also appeared on the TV talk show “The View” where he told the hosts he was living from paycheck to paycheck but that he had found happiness with his third wife. “I’m totally destitute and broke,” Tyson said. “But I have an awesome life.”