Jon Gruden
Jon Gruden was head coach of the Raiders from 1998-2001. He took over in Tampa Bay the next season Gruden led the Bucs to victory over his old team, the Raiders, in Super Bowl XXXVII. He remained coach of the Bucs through 2008. Gruden became an analyst on MNF before returning to the Raiders in 2018. He has gone 11-21 in his first two seasons during this run.