Las Vegas Raiders
It says a lot about the state of the Raiders over the past couple of decades that Jon Gruden was their best coach. Remember, he had two spells with the franchise and brought them to an AFC Championship game in 2000. The franchise traded him to Tampa but brought him back for an ill-fated spell in 2018.
Gruden’s second tenure came to a humiliating end after the email scandal. But there is a full rogue’s gallery of terrible Raiders’ coaching reigns. Art Shell and Tom Cable are two of the worst but it’s impossible to look past Lane Kiffin. His relationship with Al Davis deteriorated to nuclear levels (via USA Today Sports).