2. Dermontti Dawson
$70 million. That’s how much Dawson lost in disclosed career earnings. It’s a staggering sum of money, earned from a brilliant NFL career. To be able to lose a fortune that big should almost be admired because the closest most people will come to that amount of money is if they stand outside Fort Knox. However, the seven-time Pro Bowler somehow managed to do exactly that.

When a court declared him bankrupt in 2010, Dawson had debts of over $70 million. But the big problem was that he had less than $1.5 million left in his bank account. Unfortunately, you can’t just pay with a credit card and worry about it later. The housing crash decimated his fortune because the Hall of Famer unwisely put a lot of cash into unsustainable properties. To sum up, it’s the same, sad story.