1. Jon Gruden resigns as head coach of the Raiders
Jon Gruden left the Raiders franchise after leading them to becoming perennial winners in the AFC back in the early 2000s. Gruden would be traded to the Tampa Bay Buccaneers in 2002, and quickly proceeded to beat the Raiders in the Super Bowl, making him the youngest Super Bowl-winning head coach in NFL history.
After the trade of Gruden to the Bucs, the Raiders franchise went through nine different head coaches across the next 15 seasons, but in 2018, Gruden made his triumphant return to the organization. The arrival of Gruden was seen as the beginning of bringing the franchise back to the glory days, but that certainly was not the case.
Wins were hard to come by during the second Gruden era, and the combination of him and Mike Mayock missed on so many first-round picks. However, in 2021, just as the Raiders were starting to turn the corner, a season that would find them back in the playoffs for the first time since 2016, word came out that Gruden was implicated in an email investigation with the then-Washington Redskins.
Gruden sent emails that contained racist, misogynistic, and homophobic language, and once those were released to the national media, he resigned as head coach of the Raiders. Interim head coach Rich Bisaccia would go on to lead the Raiders to the playoffs that season, but after going 8-8 the year before, and making the playoffs in 2021, one can only think about where the franchise would be if Gruden was still at the helm.
The former Raiders head coach is back in the NFL, even spending some time coaching the hated Kansas City Chiefs, which is just another strange storyline to add to the Jon Gruden Saga.