Allen Iverson and Terrell Owens are just the latest example of athletes who made huge amounts of money during their careers, sometimes eclipsing the $100 million mark, and still managed to blow it all away before they even turned 40. A combination of fast living, bad friends and bad investments usually does the trick.

Sadly, they aren’t the first and don’t even come close to the record of big spending and big losing (Mike Tyson apparently does) in the financial market. Even sadder to say, is that they surely won’t be the last.

Mike Tyson

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Mike Tyson Earned something between $300-400 million during his boxing career, including some fights which got him over 30 million dollars. Still, the former undisputed heavyweight champion of the world declared bankruptcy in 2003. Tax debts of $27 million around the world and pretty much too many people living off him over the years, with Don King as the main leech, sucked his back account dry.

Evander Holyfield

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At 49 years of age, Evander Holyfield is still fighting and is even a pretty negligible association (WBF) heavyweight champion. One of the reasons for Holyfield’s return to the ring are his financial troubles. Despite earning over $250 million throughout his boxing career, Holyfield ran out of money at some point. Bad investments and having too many kids (11) might have done the trick. Holyfield himself declared that he does have the cash, it just isn’t liquid right now, a few years ago when he couldn’t keep up with his child support money.

Scottie Pippen

Pippen, a six time NBA champion, earned over $100 million during his career from basketball alone, but managed to blow most of it away simply on bad business instincts and probably advice. Buying a jet was probably the final straw, but a few real estate deals that turned South didn’t do his bank account any good.

Michael Vick

Vick is back on the big earners track, making quite a lot of cash playing for the Philadelphia Eagles, but his financial problems and obligations are far from ever, despite raking in over $20 million a year from football and endorsements before the dog fighting ring was exposed.

Vick wasn’t the savviest of businessmen as well, and the combination of losing all of his sponsors, salary and still supporting his family and too many friends emptied his bank account.

Antoine Walker

Gambling took away most of Antoine Walker’s money, despite earning over $100 million during his 12 year NBA career. Walker filed for bankruptcy in 2010  after being unable to pay debts of over 12 million dollars. He was notoriously charged with with three felony counts after writing bad checks to cover losses in Las Vegas casinos.

John Daly

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The only golfer to win two Majors and not get to ever play in the Ryder Cup also had quite a gambling problem. In his 2006 autobiography Daly estimated his losses in Vegas to be around $50-60 million, mostly on a $5000 slot machine. Daly was able to payoff his debts through landing new sponsorship deals and making paid public appearances.

Deuce MaCallister

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Deuce McAllister has made over $70 million during his nine seasons NFL career with the New Orleans Saints, but he and his Nissan car dealership business went under, eventually owing Nissan finance around $7 million dollars. He did have a Super Bowl ring to help him pay the bills, but that can’t be worth that much.

Allen Iverson

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Having an entourage of over 50 people hanging around with you is never really a financial MUST, and Iverson, who has earner over $150 million during his NBA career which it is unclear if it’s done or not, loved his friends around him. Gambling problems and his love for expensive lifestyle quickly led Iverson into a situation forcing him to find a basketball team, even though he probably doesn’t really feel like playing basketball anymore.

Terrell Owens

Terrell Owens is still looking for a way back into the NFL, but it seems his days as a wide receiver are over. Blowing away over $80 million in career earnings don’t just happen like that, and T.O. claims it wasn’t the fast track kind of living that brought him into this situation. Bad advice on business deals, non of them of course his fault, are mostly to blame.