“Kenny Freaking Chesney” – Nobody Gets More Pumped About Johnson City, Tennessee, Than Former NFL Coach Jon Gruden

Former NFL coach and current Barstool Sports personality Jon Gruden is apparently a huge fan of Kenny Chesney.

The former NFL coach (known most famously for his years with the Raaaiiddders) and football broadcaster has been away from the game for a while after he resigned from his head coaching position in 2021 after emails he sent that featured alleged racist, homophobic and misogynistic language surfaced. That scandal stopped the Gruden train right in its tracks, but now time has passed, and he’s starting to emerge in another lane.

Social media.

Gruden first started making waves in the online world with his “Gruden Loves Sports” YouTube page, where he posted somewhat startling content. He’s always been passionate about the gridiron, and when he started funneling all of that passion into content creation, it all came off as… a little overwhelming and scary.

This video right here gives you all the context that you need:

There’s a reason why he’s nicknamed after and compared to the horror movie staple character Chucky.

Watch just a couple of minutes of anything Jon Gruden has ever done and it becomes abundantly clear just how much Jon Gruden loves football. To be frank, it’s actually a little concerning how much he seems to love it. But his love for the game did translate to him joining on at Barstool Sports in late 2024, and he’s continued to put out world-class content while he’s been there.

Some of my personal favorite videos that he’s done have been “unboxing videos,” where Coach Gruden receives a box – usually from a sports team – and opens it up, all while talking about the place the box is from. The latest example of that is a package that Gruden received from East Tennessee State University in Johnson City, Tennessee.

Gruden described it as “arguably my favorite place in the whole world.”

Then he went into some of the famous alumni with connections to ETSU, like the legendary Steve Spurrier and former tight end Jason Witten. But the person who went to East Tennessee State University that Gruden spent a lot of time talking about was the one and only Kenny Chesney:

“You know who graduated from this place? East Tennessee State? Kenny Chesney… (he) was in a fraternity with my wife’s brother, Larry. We’ve known Kenny Chesney before he was really Kenny Chesney. Gah, I love Kenny Chesney.”

Shoutout to Gruden’s wife’s brother Larry.

The former NFL coach went on to break into a horrible, ear-drum-shattering rendition of “She Thinks My Tractor’s Sexy.” Good thing he knows football and content creation… because Gruden doesn’t have a chance at a singing career. That didn’t stop him from pointing out his favorite Kenny Chesney song though:

“My favorite song is, ‘Every sweet memory I can recall, she’s got it all.’ I can sit there and sing almost every one of his songs… by myself of course, without anybody knowing. Jason Witten, Steve Spurrier, and Kenny freaking Chesney from right here in Johnson City, Tennessee. Unbelievable.”

That song he was referring to is “She’s Got It All,” in case that wasn’t clear.

Do you think Jon Gruden has a cup of coffee for every hour of the day? Or does he just wake up with that much energy and zest for life? I’ve actually got another idea as to how Coach Gruden keeps the good vibes flowing. It might just have something to do with firing up music from one of the greatest graduates that Eastern Tennessee State University has ever seen… KENNY FREAKING CHESNEY.

“She Thinks My Tractor’s Sexy”

“She’s Got It All”

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