Jon Gruden - Cast

Jon David Gruden (born August 17, 1963) is an American professional football coach who is an advisor for the Milano Seamen of the European League of Football. He held his first head coaching position with the Raiders franchise during their Oakland tenure from 1998 to 2001, where he won two consecutive division titles and made an AFC Championship Game appearance. Gruden was traded to the Tampa Bay Buccaneers in 2002, which he led to their first Super Bowl title in Super Bowl XXXVII the same season. At age 39, he was the then-youngest head coach to win the Super Bowl. He served as Tampa Bay's head coach through 2008, setting the franchise record for wins, but made only two further playoff runs. After his firing from the Buccaneers, Gruden was featured as an analyst for ESPN's Monday Night Football broadcasts from the 2009 to the 2017 seasons.