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https://thelandryhat.com/posts/ranking-top-7-head-coaches-dallas-cowboys-history-01h83a19kyb2
Bill Parcells took on the challenge of coaching a Dallas Cowboys team with no culture. During Parcells' four-year tenure with the Cowboys, the team made it to the playoffs twice; however, they were unable to secure a win during those playoff appearances. Parcells would finish his Dallas stint with a 34–30 record and no playoff wins. His greatest accomplishment as Cowboys head coach was the development of quarterback Tony Romo. He signed the quarterback in 2003 and helped him develop into a Pro Bowl quarterback by 2006. In 2003, Dallas Cowboys' owner Jerry Jones hired Parcells as head coach after three consecutive 5-11 seasons and convinced him to come out of retirement. They famously referred Bill Parcells to as "the Big Tuna." He accomplished a remarkable feat in the NFL, leading four franchises to the playoffs and taking three of them to a conference championship game.
7. Jason Garrett (2010-2019)
Jason Garrett took charge of the Cowboys in 2010 and took them to three NFC East championships. Garrett's fundamental weakness was he was learning how to be a head coach on the job and the Cowboys only made the playoffs three times during his tenure. He received the AP Coach of the Year title in 2016. Despite finishing the regular season with an 85-67 record, Garrett only had a 2-3 record during the playoffs.6. Wade Phillips (2007-2010)
Jason Garrett's predecessor showed great prowess as a defensive coordinator but could not lead a team as a head coach. The Cowboys appointed Phillips as head coach on Feb. 8, 2007, following the retirement of Bill Parcells. This was where Phillips had the most successful head coaching tenure. Jerry Jones chose him among 10 potential replacements he interviewed, including Norv Turner, Ron Rivera, and Jason Garrett. The Cowboys suffered another playoff loss in the 2007 NFL playoffs, bringing his playoff record to 0-4. Dallas didn't qualify for the playoffs in 2008 after losing the last game 44-6 to the Philadelphia Eagles, which meant they missed out on a wild card berth. Phillips' Cowboys won their first playoff game in 12 years on January 9th, 2010, defeating the Eagles in the 2009-10 playoffs. He then signed a contract extension that ran through the 2011 season.5. Barry Switzer (1994-1997)
“Jerry actually told those guys that there were 500 coaches who could have won the Super Bowl with that team,” said Jimmy Johnson. An intoxicated comment ended the Cowboys dynasty. Jerry Jones hired Barry Switzer as the new head after Jimmy Johnson's departure. There was no immediate collapse, however, as Dallas went 12-4 in both 1994 and 1995 and won another Super Bowl title. Barry Switzer was under a lot of pressure when he took over from Jimmy Johnson before the 1994 season. He was trapped in a no-win situation. If he lost, people would castigate him, but even if he won, Jimmy Johnson would get all the credit. Switzer achieved a significant amount of success despite high expectations. He holds the record for the highest winning percentage in the history of the Cowboys. His career NFL coaching record was 40-24 when he resigned following a disappointing 6-10 season in 1997.4. Mike McCarthy (2020-present)
Mike McCarthy's overall regular season record as an NFL head coach is 155-97-2 over 16 seasons. Tom Landry, Chuck Noll, Andy Reid and Bill Belichick are the only other head coaches, besides him, to lead one franchise to eight straight playoff appearances. Posting back-to-back 12-win seasons shows you are heading in the right direction. The Cowboys haven't accomplished this since the 1993-95 seasons.3. Bill Parcells (2003-2007)
Regardless of what the case was. Despite the lack of playoff achievements, Parcells established a solid foundation for the future success of the Cowboys.Bill Parcells took on the challenge of coaching a Dallas Cowboys team with no culture. During Parcells' four-year tenure with the Cowboys, the team made it to the playoffs twice; however, they were unable to secure a win during those playoff appearances. Parcells would finish his Dallas stint with a 34–30 record and no playoff wins. His greatest accomplishment as Cowboys head coach was the development of quarterback Tony Romo. He signed the quarterback in 2003 and helped him develop into a Pro Bowl quarterback by 2006. In 2003, Dallas Cowboys' owner Jerry Jones hired Parcells as head coach after three consecutive 5-11 seasons and convinced him to come out of retirement. They famously referred Bill Parcells to as "the Big Tuna." He accomplished a remarkable feat in the NFL, leading four franchises to the playoffs and taking three of them to a conference championship game.
2. Jimmy Johnson 1989-1993)
Jimmy Johnson turned a 1-15 laughingstock team into one of the great dynasties in NFL history. The Dallas Cowboys teams he built won three Super Bowls in four years. Success was not enough for the owner and the head coach. Jones and Johnson's strained relationship led to the Dallas coach leaving the team after the 1993 season. Johnson's potential to lead the Cowboys to four consecutive championships left many disappointed.1. Tom Landry (1960-1988)
Besides his record 20 consecutive winning seasons from 1966 to 1985, Landry won two Super Bowl titles (in Super Bowl VI and XII), five NFC titles, and 13 divisional titles.Between 1966 and 1982, Dallas took part in 12 NFL or NFC Championship games. From 1970 to 1982, the Cowboys appeared in 10 NFC Championship games within 13 years. In 1990, Landry was inducted into the Pro Football Hall of Fame. They referred to him as the man in the hat. Many considered Landry as one of the most iconic head coaches in NFL history, specifically for the Dallas Cowboys."Landry built the 4–3 defense around me. It revolutionized defense and opened the door for all the variations of zones and man-to-man coverage, which are used in conjunction with it today. "
- Sam Huff