Jason Caffey Made $35,000,000
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. First, there was an assault on a male stripper in 2003.
Then, 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. Apparently no one ever told Caffey that condoms are cheaper than lawyers.
Mookie Blaylock Made $32,000,000
Mookie Blaylock was a defensive-first point guard who became the third player ever to lead the NBA in steals in consecutive seasons. But while he could protect the defensive end of the court, he couldn’t protect the $32 million he made in his career and had to resort to bartending in retirement.
But Blaylock’s issues go beyond financial woes as he became a full-blown substance abuser after his playing days were done. He had no fewer than seven DUIs, including one where his blood alcohol content was four-and-a-half times the legal limit.
While it would be nice if Blaylock made a complete 180 and turned his life around, unfortunately, that is not the case. In 2014, while driving on a suspended license, Blaylock was involved in a head-on collision that took the life of a mother of five. He was sentenced to seven years in prison followed by eight years of probation.