Year: 2008
Contract: 6 years, $111 million

One thing Gilbert Arenas is, is honest. Just last month, he admitted that he might've signed the worst contract in NBA history. It was a pretty terrible experience for all parties involved. After re-upping with Washington, Arenas dealt with injuries and also an infamous incident in which he brought firearms into an NBA arena. After that, the Wizards eventually got rid of Arenas in a trade to the Magic for another bad contract in Rashard Lewis. We will forever miss Hibachi.