Year: 2008
Contract: 6 years, $111 million

There was a time when Gilbert Arenas was one of the league's top gunners. Yeah, we know. But really. The 2006-07 season was one full of buzzer beaters and high scoring performances for Gil, including a classic battle where he dropped 60 on Kobe himself. The Hibachi's ability to light a box score on fire paired with his out-sized personality made him a fan favorite. But then it all started to fall apart. Arenas played only eight games in 2007-08 with a crippling knee problem. The Wizards, desperate to maintain relevance, re-signed Arenas that summer for what many considered to be a ridiculous deal. They were right. Gil played in just two games in 2009 and even that wasn't until March. In 2010, things looked as though they were headed in the right direction, then Gil brought out the big guns. Literally. We all know what happened: storing guns in the locker room, finger guns, fake apologies, and finally, a season long suspension from Papa Stern. Gil was traded to Orlando 24 games after his return and waived under the amnesty clause just 49 games after that. Talk about going out with a bang.