Gregg Giannotti thinks parts of Barstool gig ‘losing its luster’ for Jon Gruden

Jon Gruden is one of us.

He hates commercials — a true football guy’s football guy.

But as Gruden grew visibly irritated with the endless ads during the AFC and NFC Championship Games — streamed live from Barstool’s Gambling Cave on Sunday — Gregg Giannotti began to notice cracks in the foundation of Gruden’s partnership with Dave Portnoy’s company.

Giannotti, who co-hosts Boomer & Gio with Boomer Esiason on WFAN, has previously taken aim at Barstool Sports — albeit jokingly. During the New York Mets’ run to the National League Championship Series, he quipped that the watch party looked like the cantina scene from Star Wars.

“It’s an interesting group,” he joked at the time.

While he didn’t specifically target Gruden’s cohorts on Sunday, Giannotti sensed a growing disinterest in Gruden’s Barstool role.

“He’s starting to lose it a little bit,” Giannotti said on Boomer & Gio. “Not ‘lose it’ — he’s starting to get annoyed with parts of the job. You can tell because him sitting there and watching those football games with those guys, I think, is losing its luster to him.

“The last time he was doing it — last week — he did the old, ‘I wish I was home watching The Walking Dead, man.’ ‘Just innocent people getting snarfed.’ So, he said that. And then there’s this video with his face. And, you know, you’ve seen enough of Gruden on the sideline; you’ve seen enough of him on Monday Night Football. He’s got this face where he is so annoyed. And he’s watching this Taco Bell commercial, and he can hear these people screaming in the background… ‘Man, if I see one more commercial, I’m gonna kill myself.'”

Giannotti made it a bit more PG-13, as Gruden joked about “blowing his brains out” or “ODing on sleeping pills.”

I can’t stand all the commercials… pic.twitter.com/zYsaCGiNlY

— Jon Gruden (@BarstoolGruden) January 27, 2025

Can you tell this guy wants to be back on a sideline somewhere?

Giannotti speculated that Gruden’s Super Bowl appearance with Barstool might be his last livestream with the brand.

“I bet that after he does the Super Bowl and watches the Super Bowl with those guys, you’re not going to see him watching any more games with those guys,” Giannotti said, as covered by Barrett Sports Media.

At the same time, he also brought up a good point about Gruden’s current viewing experience.

With Red Zone and Sunday Ticket, there are no commercials during the games. But for standalone matchups, it’s just a relentless stream of ads. And Gruden seems like he can’t stand to listen to Taco Bell and Burger King jingles on an endless loop much longer than he has to.

So, while Giannotti may not have been entirely serious about Gruden, someone with aspirations to return to coaching—even if his Barstool venture has helped rehab his image—might not be able to stomach many more live streams and endless commercials.