Chuck Noll, of the Pittsburgh Steelers - he won Superbowls VIII and IX (1974 and 1975 seasons) and XIII and XIV (1978 and 1979 seasons).
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Terry Bradshaw is famous for being a four-time Super Bowl champion. He is also a two-time Super Bowl MVP, winning the awards as the starting quarterback for the Pittsburgh Steelers.
Jon Gruden:Mike Tomlin, Pittsburgh - XLIII (36 yrs, 323 days)Jon Gruden, Tampa Bay - XXXVII (39 yrs, 162 days)John Madden, Oakland - XI (40 yrs, 274 days)Joe Gibbs, Washington - XVII (42 yrs, 66 days)Chuck Noll, Pittsburgh - IX (43 yrs, 7 days)Don Shula, Miami - VII (43 yrs, 10 days)
Jimmy Johnson won two Super Bowls as the Dallas Cowboys head coach.XXVII (1992) and XXVIII (1993)
The Steelers won four Super Bowls during that time span. Winning in the 1974, 1975, 1978 and 1979 seasons.
I honestly can't say he does. At the time, he did not have a great relationship with head coach Chuck Noll and might have felt like an outcast. But as time went on and everyone got on the same page, he became a lot more comfortable with the situation. I don't think he would trade winning four Super Bowls and two Super Bowl MVP Awards for anything else.