7. Dick Jauron (2006-2009)
Record: 24-33
Similar to Chan Gailey, the Buffalo Bills were leaning into experience at head coach as they tried to end their playoff drought. In 2006, the Bills would hire Dick Jauron to be their head coach and he would remain in that role for about two and a half seasons before being fired midway through the 2009 season.
Dick Jauron previously was head coach of the Chicago Bears and even got the Bears to the playoffs in 2001 with a 13-3 record. He would be fired after the 2003 season and join the Detroit Lions as defensive coordinator.
Jauron would step in as interim head coach after Steve Mariucci and go 1-4 over the final five games as head coach.
With the Buffalo Bills, Jauron was pretty consistent as the team would go 7-9 the first three years he was head coach. The best chance to end the playoff drought was in 2008 when the Bills began the season with a 5-1 record.
However, Trent Edwards would suffer a concussion against the Arizona Cardinals in Week 6 and the Bills would not be able to bounce back, ending the season with a 2-8 record. He would return in 2009 but after losing six of their first nine games, he was fired as head coach.