1. Hue Jackson:
Jackson found measured success as the offensive coordinator of the Redskins, Falcons, Raiders, and Bengals. Many on this list have put forth a similar body of work only to be hired and fail as a head coach. Jackson took over as the head coach of the Oakland Raiders in 2011. His first season actually wasn’t all that bad on paper, as he went 8-8. But the Raiders started out hot at 7-4 and missed the playoffs after dropping four of their final five. That was enough to get Jackson a one-way ticket out of Oakland in only one year.
He rebounded well with Cincinnati from 2012-2015 and was hired by their division rival Cleveland Browns before the 2016 season. What followed was arguably the least successful run with any team in NFL history. Jackson went 1-15 in his first season but somehow got a second chance. He followed it up by the only worse result, an 0-16 season in 2017. For reasons unbeknownst to anyone, Jackson was given the reigns for a third year in 2018. Perhaps the team thought that with their years of stockpiling draft picks and talent, he could finally break through. He did better the next year but was fired after starting the season 2-5-1. He reportedly clashed with outspoken No. 1 pick Baker Mayfield. Jackson ended his Browns run with a 3-36-1 mark and is currently out of pro football.
It’s been a long, brutal list of the least successful NFL coaches, yet it’s Jackson who takes the top spot for his sheer ineptitude at turning around one of the most beaten franchises in sports.