1. Eddy Curry

Year: 2005
Contract: $60 million/Six years
Team: New York Knicks
Eddy Curry's deal was just another big contract that came in an era where the Knicks seemingly just threw millions of dollars to players who hadn't really proved their consistency. During his tenure with the Knicks, Curry routinely showed up to camp out of shape and showed a lack of effort that was reflected in career lows. One of his lowest points came in the 2008-09 season when he only played in three games and scored five points total for the season.