Estimated Career Earnings: $19,000,000
How They Lost It All: If it's not through buying Cartier watches and fathering children, then athletes lose millions through greedy agents and divorce—Bernie Kosar lost everything through a ruthless combination of the latter. The former Browns quarterback lost half of his earnings in a nasty divorce and the rest in a combination of bad real estate deals and unpaid loans from, amongst others, the Cleveland Browns. As if playing in Cleveland wasn't agonizing enough, Kosar is now indebted to the franchise.