10. Jon Gruden
Some might consider this a controversial pick but Gruden hasn’t set the world on fire since his Super Bowl win back in 2002. Furthermore, many believe that he merely benefited from the team that Tony Dungy left behind. That’s obviously too simplistic but he did follow up his crowning glory with two losing seasons and embarked on a journey into mediocrity.

Now he’s back with the Raiders, the team where he first made his name. After a winning start, Gruden followed up with two losing seasons. One of his key issues is that he’s stubborn as his devotion to Derek Carr shows. He already set the Buccaneers back but now he’s in danger of doing the same to the Raiders. Has his time passed by?