Jon Gruden
On the sideline or in the booth, Jon Gruden is always a coach. The current ESPN NFL analyst is also a Super Bowl champion from his days at the helm of the Tampa Bay Buccaneers. At the time, "Chucky" -- as he affectionately called due to his resemblance to the eponymous horror film doll -- was the youngest head coach ever to win the big game at age 39.
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