Jason Caffey: Career Earnings, $35 million
Jason Caffey is best known for two things: parlaying his minor role on the Chicago Bulls into a (ridiculous) seven-year, $35 million contract with the Golden State Warriors, and the awful decisions he made off the court. The Warriors immediately regretted overpaying for Caffey, and proved it by buying out his contract after just one season. From there, the legal troubles (and legal fees) began.
In 2008, he was sued for failure to make his required child support payments. In Caffey’s case, he owed monthly child support payments for 10 children by eight different women! At one point, he even served an eight-day sentence for failure to pay his child support payments.