Barstool Sports Hires Disgraced Jon Gruden, the Unhinged Human Aneurysm

NFL fans may remember that racist Jon Gruden took the 2002 Tampa Bay Buccaneers team that homophobic Tony Dungy built and won a Super Bowl with it, which led people to believe that he was some kind of genius until he was eventually drummed out of Tampa Bay and into the announcer’s booth, where he spent Monday nights for eight years growling into a microphone and praising certain NFL quarterbacks in ways that felt borderline homoerotic.

After a long stint on ESPN, however, Gruden returned to coaching, taking over as the Oakland Raiders head choad, where he was thoroughly mediocre before a workplace harassment investigation into the Washington Football Team unearthed emails Gruden sent that were so racist and so homophobic that the same league that turns a blind eye to domestic violence, murder, and Tony Dungy’s insistence that we’re all going to hell had no choice but to fire Gruden. The emails were bad — he said of NFLPA Executive Director DeMaurice Smith, for instance, that “Dumboriss Smith has lips the size of michellin [sic] tires” and sent around topless photos of Washington Football Team’s cheerleaders among other things.

In other words, Jon Gruden is not only exactly the kind of guy who voted for Donald Trump, but he f**ked his ballot in the polling booth, so eager was he to illustrate his MAGA bona fides. He’s also been angling to get a new head coaching job in the NFL for years, but Gruden is so disgraced that not even Jerry Jones or Woody Johnson will hire him. He’s had no luck in the college ranks, either.

With little else to do while waiting for the nation to completely normalize racial slurs again, Jon Gruden has taken to content creation on TikTok, where he recounts the previous week’s highlights with the crazed eyes of a teenager who has found an unsoiled sock while rocking in his chair like DiCaprio angling for an Oscar. The level of cringe and desperation is palpable. Here’s the most recent video. It has to be seen to be believed:

@grudenlovesfootball Coach Gruden is FEELIN' NICEY after seeing Saquon Barkley, Tyler Bass and Kerby Joseph's PRIMETIME performances in Week 9! 🏈 #grudenlovesfootball #NICEY #nfl ♬ original sound - Gruden Loves Football

This is a 61-year-old man sporting Ben Stiller’s haircut in Simple Jack while bleating into the camera looking like Vincent D’Onofrio in Full Metal Jacket seconds before he blew his brains out. I would not trust him in the room with my worst enemy.

Naturally, he’s been hired by Barstool Sports, the sports outlet of choice for pissant bros who didn’t get enough love from their fathers and beat their heads against brick walls because they want to know what it feels like to have a concussion. It’s the kind of place where light misogyny and homophobia are encouraged, and where all the human protein powder shakes are dying to spend three hours telling you about their fantasy teams. In other words, Jon Gruden will fight right in.

Dustin lives in Portland, Maine. You can follow him on Bluesky.