1.) Jon Gruden: 57-55 overall record
Gruden edges out Dungy for the top spot on this list. Despite winning a Super Bowl in his first season as coach, Gruden’s remaining tenure was rather disappointing. The Bucs made the postseason just twice over the next six seasons, losing both times. Tampa Bay hasn’t won a postseason game since their Super Bowl XXXVII win. If they want a shot at playing in Super Bowl LV in Tampa, they’ll have to take care of business on the road in Vegas against Gruden’s Raiders.
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