3. Jon Gruden (1998-01, 2018-Present)
There are two eras of Jon Gruden as head coach of the Raiders and round one was decidedly more successful than round two has been so far. Al Davis took a chance on the young Gruden in 1998 and he repaid that faith with four-straight non-losing seasons and were it not for one of the worst calls in NFL history, a trip to the AFC Championship in 2001 as well. The former Eagles OC went 38-26 and produced three top-10 scoring offenses to earn the distinction as an offensive genius.
Gruden and Davis’s relationship ended poorly after that 2001 season but he had the Raiders humming, especially on offense, in his final two seasons. Gruden resurrected the careers of Rich Gannon and Jerry Rice and became a fan favorite in Oakland for his intensity and more importantly, his winning.
Things have not gone quite as smoothly in Gruden’s return to the Silver and Black but the team is trending upwards and the switch to Las Vegas could be a great thing for all involved. Gruden still has 8 years left on his contract so he may end up climbing or dropping on this list but he will have some work to do to catch up to the men ahead of him.