24. Jay Gruden
After building up an impressive resume as a specialist coach in the AFL and NFL, he became head coach of the Washington Redskins in 2014. Things started off well. He posted three winning seasons in a row, including a playoff appearance in 2015. But that was as good as it got for Gruden in DC.
The Redskins went 7-9 in 2017 and 2018, before slumping to 0-5 in 2019. Five years after signing up, the team was in total disarray. To be fair, it wasn’t totally his fault that the team failed to perform. The franchise is rotten to the core, but still, he overstayed his welcome as head coach. It probably came as a relief for him.