Grant Hill, Orlando Magic, 2000: seven years, $93 million
Hill's impending free agency was on everyone's mind in 1999. The Orlando Magic and the Chicago Bulls made a series of trades to set aside cap space for the five-time Detroit All-Star, who was asked about his future following nearly every Pistons win or loss. Anxious to prove that he was a team-first, free-agency-second type of player, Hill needlessly played on a broken ankle in Detroit's first-round playoff loss, setting up a disastrous run with the Orlando Magic -- one that has seen him play only 135 games in six seasons due to recurring injuries.