22. Andy Reid
Reid coached the Philadelphia Eagles for 14 seasons and made his fair share of good and bad decisions throughout that time period. Of course, he’s one of the most respected coaches in the game in 2020, but it hasn’t always been smooth sailing for the Super Bowl winner. Reid didn’t ruin his own reputation but he definitely tarnished Juan Castillo’s by giving him the defensive coordinator job in 2011.

Nobody expected this because Castillo hadn’t coached defense since his time at Texas A&M in 1989. The former offensive line coach experienced a nightmare season and the Eagles fired him in 2012. But at the end of the day, it was Reid’s call to give Castillo the job in the first place. Castillo is still in football as offensive line coach for the Chicago Bears but may struggle to find another coordinator job anytime soon.