Jon Gruden’s Quest To Coach Again Takes A Detour At The Dipshit Factory

Disgraced former NFL coach Jon Gruden has spent the last few years desperately trying to return to his craft. Gruden lost his head coaching job with the Las Vegas Raiders in 2021, after emails in which he used racist, homophobic, and sexist language were leaked to the press. In one of those emails, he wrote that "Dumboriss Smith has lips the size of michellin tires," in reference to then-NFLPA head DeMaurice Smith. Gruden resigned from his position with the Raiders in October 2021, and then popped up the following year, sporting a Mark Davis-lite haircut, to half-heartedly apologize for the things he wrote.

That didn't do the trick, so Gruden has spent the last two years coming up with other ideas. He managed to weasel his way into the Kansas City Chiefs' training camp this past summer, but that didn't lead to any jobs. Then he sat down for a profile with CBS Sports in September, in which he revealed that his new goal was to get a job coaching college football. Still, no coaching opportunities materialized, which left Gruden stranded with one final option: content creation.

About two months ago, Gruden launched a YouTube channel called Gruden Loves Football, where he began posting videos with the kind of tone and quality that immediately makes you feel sorry for whoever was tasked with running the camera. In one of his first videos, Gruden gave a tour of his strange home office, where he showed off rooms dedicated to each era of his coaching career. "This is where you go when you get fired, traded, or trampled to death by coaching," Gruden said at the start of the tour. "So I needed a place to go and keep studying, because I'm trying to get one more shot." (Let's also take a moment to acknowledge Gruden's opening line in this video: "When you get fired as a coach, it's not very good." Danny McBride couldn't have said it better.)

At some point, it appears that an overpriced brand consultant involved in Gruden's media pivot issued some vibes-based advice to the old man, which drove him to TikTok. That's where the coach has been posting videos of himself twitching and spitting in front of a laptop screen while shouting about which NFL players make him feel "nicey."

Remember, all of this was meant to get Gruden a coaching job. Thursday morning, he signed a deal with Barstool Sports, where he'll be colleagues with a bunch of rapidly aging guys whose primary job responsibility is filming themselves watching sports while getting upset about their parlays not hitting. Keep on grinding, Jon.