Shawn Kemp: 7 years, $107 million (1997)
As one of the great (if not underrated) stars of the late 1990’s, Shawn Kemp was extremely displeased with the Seattle Supersonics handing center Jim McIlvane a huge free agent contract, as opposed to taking care of the home-grown Kemp. Kemp demanded a trade, and was sent to the Cleveland Cavaliers prior to the 1997 season.
Cleveland game him the money he sought, in the form of a seven-year deal worth $107 million. But when the NBA lockout shortened the 1998-1999 NBA season, that’s when Kemp’s issues with substance abuse and weight gain began to destroy his once-spectacular NBA career.