Jaguar PS /

6 Evander Holyfield

One of the greatest boxing champions of all times, Evander Holyfield earned more than $230 million in prize money, not to mention endorsements, commercials, etc.

Enough to last you a lifetime or make that a decade or so. Now, six years after his retirement, Holyfield is broke, barely worth $500,000. He’s sold most of his possessions, including his hard-earned medals.

Jamie Lamor Thompson /

5 Alyssa Milano

The Melrose Place star is another of those who imagined they’re set for life and lived way above her means while banking on her early career success.

While she hasn’t made a decent movie in years, Milano spent $5 million on renovating her California home. And who’s to blame for the fact she’s now millions of dollars in debt?

Well, not her, obviously, but her business manager, who, according to the actress, did not warn her she needed to make more money. Seriously, like how old are you, five? Can’t you do the math?

s_bukley /

4 Aaron Carter

The rapper started his career at the age of 9 and made more than $200 million by 18. Life seemed easy for Aaron Carter, and you can’t blame him for being a stupid kid.

Most 18 years old cannot be trusted with $1,000, let alone a fortune of that size. In 2013, he owed several million in unpaid taxes, so he had to file for bankruptcy.


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