Bankrupt: Mike Tyson and 5 Boxers from the Past 20 Years Who Ended Up Broke | News, Scores, Highlights, Stats, and Rumors

Mike Tyson, once the "baddest man on the planet," earned at least $300 million during his boxing career. Even with the inevitable expenses and taxes, it seems like this would have been enough to be financially secure for life.

It didn't work out that way.

Tyson's financial issues came from a few different areas.

First, as any parent can tell you, children are expensive. So are wives. Ex-wives and children of world-famous boxers, it turns out, can be really expensive. Given that Tyson was married three times with at least eight children, a good portion of Iron Mike's net worth ended up in the hands of a variety of women and kids.

Second, Tyson liked to live large. Extremely large. Most everyone knows about his pet tigers, and his spending sprees on jewelry and cars are legendary. Add a near fetish for purchasing property, and you can spend through a fortune pretty quickly, as Mike found out. An gigantic entourage of many employees that supports your lifestyle gets expensive quickly as well.

Finally, if Mike thought women were expensive, he apparently learned that they were nothing compared to lawyers. Mike's multiple legal issues, including the infamous rape case, drained millions from his coffers.

By 2004, Tyson had accumulated over $38.4 million in debt. Needless to say, bankruptcy was his only option.

Since that time, in fits and spurts, Tyson has shown signs of turning his life around and managing his finances better. Mike still has some earning power based on his fame and is reportedly living a reasonably comfortable life. Hopefully he can keep it up.