Gilbert Arenas: 6 years, $111 million (2008)
Gilbert Arenas was one of the best 15 players in the NBA during the 2006-2007 season, but the following season, he only played in 13 games as a result of torn MCL. When Arenas became a free agent, he demanded top dollar. Arenas would be given a six-year, $111 million contract by former Wizards General Manager Ernie Grunfeld, despite Arenas’ injury the year prior.
Less than two years later, Arenas would be suspended indefinitely from the NBA after admitting to bringing a firearm into Washington’s arena, as a result of a dispute with teammate Javaris Crittendon.