Mike Tyson: $3 Million
Mike Tyson, known for his face tattoo and appearances in "The Hangover" movies, was the dominant force in 1980s boxing. Tyson's early career was marked by impressive achievements, including winning his first 19 fights by knockout, with 12 occurring in the first round. He still holds the record for being the youngest heavyweight champion ever, achieving the feat at just over 20 years old. However, due to a high-profile divorce, legal issues, and extravagant spending, Tyson eventually squandered nearly all of his $300 million fortune. He filed for bankruptcy in 2003 and officially announced his retirement two years later.