Estimated Career Earnings: $50,000,000
How They Lost It All: During a hearing to have his child support payments lowered, the former Ravens cornerback claimed he was so broke that he was living with his parents who provided him with basic living expenses. That's right, a dude that once inked a $55M contract was back to negotiating an allowance and sharing a wall with his post-retirement, reinvigorated, bumping-uglies-every-night mom and dad. That shit's awkward, but not as outrageous as this truck he pulled up to Ravens training camp in.