JaMarcus Russell
Al Davis desperately wanted Russell to become the Raiders’ franchise quarterback. He went against Lane Kiffin’s wishes to make the LSU star the first overall pick in 2007. Russell had a good college career at LSU but his attitude concerned NFL scouts (via USA Today).

Nonetheless, the Raiders got their man after they handed him an outrageous contract. He held out and secured a staggering $68 million. Russell threw 18 touchdown passes and 23 interceptions in three seasons. In the end, they let him go and he became one of the NFL’s biggest busts.