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Gregg Giannotti: I Don’t Understand How Jon Gruden Fits into Barstool Sports

“I’m just trying to figure it out … Interesting. I did not expect that.”

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In a surprising announcement, it was announced Thursday the former NFL head coach and ESPN Monday Night Football analyst Jon Gruden had inked a new content deal with Barstool Sports. WFAN host Gregg Giannotti wasn’t sure what to make of the news as it broke.

”That’s an interesting one for me,” Giannotti said on Boomer & Gio Thursday morning moments after the news was announced. “He does those TikToks, which are very funny. I don’t know how they’re going to use him.”

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When he questioned why Gruden, who has made no bones about his interest in returning to the coaching profession, would make a deal with Barstool Sports, co-host Boomer Esiason said he understood the partnership.

”This is for now. The deal could be null-and-void if in fact he gets a job (in the NFL),” Esiason said, stating that Gruden has “that man personality” that Barstool Sports seems to love.

“But how are they going to use him? Knowing what they do and their programming, are they gonna have him watch games on live streams?” Giannotti questioned. “Maybe that’s what it is. I’m just trying to figure it out … Interesting. I did not expect that.”

Esiason was less shocked by the news, stating he could understand the thought process from the company founded by Dave Portnoy.

”They’ll just put a camera down in his office down there in Tampa,” the former NFL QB said. “He’s watching all the film and breaking down the tape. Who knows? Maybe they’ll do a postgame thing where he’s breaking down the tape. Cause you’ve seen him on Instagram, he’s hilarious.”

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