Bernie Kosar, the famously brainy Cleveland Browns quarterback (he graduated from the University of Miami in only two-and-a-half years), took his share of bone-crunching hits in the NFL, including blindsided sacks from Lawrence Taylor, Joe Klecko and other defensemen twice Kosar's size that knocked out four of his molars. But Kosar took some of his worst hits off the field in a string of financial meltdowns and personal crises.
A consummate entrepreneur, Kosar launched businesses while still an NFL player, including ownership of a 6-percent share in an outsourcing company that sold for $500 million [source: Le Batard]. He bought an arena football league team, launched a company that built football websites and magazines, and bought loads of real estate in Florida, which unfortunately turned out to be ground zero for the housing collapse [source: Schoenberger].
Kosar was successful enough to have a wing of the University of Miami business school named after him, but he was also generous with teammates and family that asked him for personal loans [source: Le Batard]. Maybe too generous. At various points, Kosar estimates he was spending in the "eight figures" to support 25 to 50 different families [source: Holmes].
When Kosar filed for bankruptcy in 2009, he owed $9.7 million to Florida Bank for failed real estate deals, $3 million to his ex-wife, and hundreds of thousands more to friends for personal loans [source: Shoenberger].