Born in Sandusky, OH, Jon Gruden played quarterback on the amateur level before starting his coaching career. He became the youngest head coach to win a Super Bowl, when he led the Tampa Bay Buccaneers to a championship in Super Bowl XXXVII. Gruden did some broadcasting, but returned to the NFL last season with the Raiders. Gruden wore #1 on his Celebrity Jersey Card. That number was probably most notably worn by Sean Rodriguez.