Estimated Career Earnings: $50,000,000
How They Lost It All: LT lost a fortune with lavish spending, hard partying, and by sniffing—doing a lot of sniffing. Since leaving the league, Taylor's been arrested a handful of times for drug possession, was caught by the IRS filing a false tax return, and declared bankruptcy in the late 90s. Standard retired linebacker stuff.

After seemingly pulling his life together, the two-time Super Bowl champ was inducted into the Hall of Fame and made cameo appearances in a handful of movies. Happy ending? Not on this list. In a demonstration of priorities as twisted as Joe Theismann's leg, LT was sued for failing to pay child support while, at the same time, shelling out $300 to allegedly have sex with an underage prostitute. Not a good look.