Year: 2007
Contract: 6 years, $118 million

Rashard Lewis skipped college and declared himself for the NBA Draft in 1998. He suffered one of the more embarrassing moments of his career that night, left by his lonesome in the green room until the second round when Seattle scooped him up. Rashard rewarded the Sonics with some sharp shooting and several signs of potential, including the franchise record for most made three pointers. But in May of 2007, he opted out of his deal and somehow convinced the Magic to a sign and trade maximum contract. Unfortunately, Shard learned of the expectations that come along with such a handsome reward and wasn't the leader or producer that his pay grade demanded. Stuck in salary cap hell and unable to rebuild with his burdensome contract, the Magic traded Lewis to the Wizards in 2010 for Gilbert Arenas. Yup. That's how much they wanted him gone.