21. DeAngelo Hall

Year: 2008
Contract: $70 million/Seven years
Team: Oakland Raiders
After trading draft picks to Atlanta in order to get Hall, the Raiders sealed the deal with this ridiculous contract that included $24.5 million guaranteed. Hall was "unable to adapt to the Raiders' man-to-man style of defense" a.k.a. fam was getting torched on the regular by wideouts all over the league. By November he was released by the Raiders, who did so to avoid having to pay an additional $16.5 million in injury-guaranteed bonuses. Hall made $8 million in eight games played. SMH, yet they let Nnamdi Asomugha get away for less money overall this offseason.