5. Mike Tyson

For years, no other boxer on earth was as feared as Tyson and Iron Mike was one of the highest paid boxers of all times, however, his powerful blows were of no use to him when he started overspending and got hooked on a lavish lifestyle.

Mike won his first 19 professional fights by knockout and many of them took place during the first round.

He soon became the heavyweight champion of the world and everything seemed to be coming up roses for this strong and charismatic fella, but in 1992 he was convicted of sexual assault and served three years in prison and when he got out his career started going south.

His downward spiral escalates after biting off a piece of Evander Holyfield’s ear during a 1997 fight, and he got disqualified. He never again won another championship.

But money shouldn’t have been a problem for Tyson since he had earned more than $400 million during his boxing career, right? Well, not exactly. He managed to spend almost all of it, frittering it away on extravagances.

He bought ridiculously huge mansions, luxury cars and even pet tigers. He also owed $9 million for his divorce settlement and $13 million to the IRS. When he filed for bankruptcy in 2003, he claimed debts of $27 million.