Contract: 7 years, $100 million ($41 million guaranteed)
Team: Washington Redskins
In a long list of terrible contracts by the Washington Redskins, this is the worst of them all. Following an impressive 2008-09 season with the Tennessee Titans where Albert Haynesworth had 75 tackles and 8.5 sacks, teams were aggressive in trying to land the hot defensive commodity. In fact, according to ESPN's John Clayton, "at least" six teams offered Haynesworth as much as $30 million in guaranteed money. In a matter of hours, the defensive tackle went with the Redskins. The 'Skins won the Haynesworth sweepstakes, or at least, that's what they thought.
The following season, Haynesworth became an incredible nuisance for the organization. He refused to participate in offseason workouts, failed a fitness test, repeatedly feuded with the coaching staff and even called out defensive coordinator Greg Blache after being sent home by head coach Jim Zorn for disciplinary reasons. In his two seasons with Washington, Haynesworth had only 6.5 sacks, a far cry from what the team was hoping for when they signed him to the lucrative deal. On July 28, 2011, Haynesworth was sent packing to the New England Patriots for a fifth-round pick.