Tom Landry is the longest tenured coach in NFL history as he coached the Dallas Cowboys from 1960 until 1988.
Jeff Fisher is the longest tenured head coach still in the league. He has coached the Tennessee Titans since 1994.
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George Halas.
Halas spent 40 seasons as head coach of the Chicago Bears franchise (1920-1929, 1933-1942, 1946-1955, 1958-1967).
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Wade Phillips, currently the coach of the Dallas Cowboys, has lead 4 teams to the NFL playoffs in his 31-year coaching career.
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Tony Dungy forever!
bum phillips As far as head coaches winning an NFL championship it is Dan Reeves who coached 23 seasons and 357 regular season games without winning a Super Bowl. Reeves coached teams to 4 Super Bowls (Denver 3 and Atlanta 1) but lost each one. Next comes Chuck Knox with 22 seasons and 334 regular season games as head coach. Knox did not coach a team to the Super Bowl. Next comes Marty Schottenheimer with 21 seasons and 327 regular season games as head coach. Marty did not coach a team to the Super Bowl.