19. Lane Kiffin
Al Davis called Kiffin “a disgrace to the organization” after he fired him following a disastrous rollercoaster of a coaching tenure (via NBC Sports). Kiffin didn’t even keep his job for two seasons before Davis lost patience. He was the youngest head coach in NFL history when he signed up in 2007. This came after his reputation soared at USC. But he was up against the wall from the beginning when the Raiders drafted JaMarcus Russell.

Russell went down as one of the biggest draft busts in history. Meanwhile, Kiffin’s relationship with Davis deteriorated to toxic levels. Kiffin refused to quit after a 4-12 season and infuriated his boss. The owner also tried to prevent his head coach from play-calling (via Sports Illustrated). The pair continued to fire shots at each other after Kiffin’s departure. It’s a shame because the Raiders were the biggest loser.