Tony Dungy (Indianapolis Colts)
Tony Dungy was a defensive specialist in the NFL who was the head coach of the Tampa Bay Buccaneers from 1996-2001 before they traded for Jon Gruden.
In 2002, Dungy became head coach of the Indianapolis Colts, and he was there through 2008, some of the prime years of Peyton Manning.
That’s largely why he falls on this list.
Dungy was given some of the best years of Peyton Manning, an MVP candidate every single season and a player who transcended the game at his position, and winning just one title was simply not enough.
As a head coach in the NFL, Dungy won nearly 67 percent of his games in the regular season, an incredible achievement. He’s a Hall of Fame coach but the inability to perform late in the postseason with the Colts is a swing Dungy would probably love to have back.
The Colts made the playoffs every single year of Dungy’s tenure, but they were one-and-done four times and only made it to the AFC Championship game twice.