Fox Sports 1
Former NFL tight end Greg Olsen, who has been a featured guest on Monday episodes of the new Barstool Sports morning show Wake Up Barstool, got a bit testy with company founder Dave Portnoy during the September 21 episode of the show.
Greg Olsen — a former Pro Bowl tight end who played for the Chicago Bears, Carolina Panthers and Seattle Seahawks — was one of the earliest pro athlete supporters of Barstool Sports and has thus known Dave Portnoy for quite some time.
Nevertheless, the usually affable Olsen had to put the 48-year-old media personality in his place after relentless ribbing about his outfit choices.
After the nearly 50-year-old Portnoy mocked Olsen for his “preposterous look” and logo-less hat, a frank Olsen countered with a couple of responses, first saying that if he keeps having to take crap from Portnoy, he’s simply going to bail on the show.
Olsen didn’t relent there, though, as he then called out Portnoy for not necessarily being in a position to comment on how other people look.
Greg Olsen put Dave Portnoy in his place over constant bashing on Wake Up Barstool
“Hey, listen, I’m just gonna be honest — if I’m going to keep getting a hard time from this show, I might just bag Monday mornings. You guys are on your own — deal with it, good luck,” a fed-up Olsen proclaimed.
After Portnoy said that Olsen “bagged it” last Monday, Olsen threatened to do the same next week before saying:
“At what point are you Mr. Fashion? You’ve got some bad outfits. You’re real critical of everybody else’s look for a guy who’s not the best looking guy — let’s just be clear.”
Greg Olsen already sick of Dave Portnoy😂😂 pic.twitter.com/C4erNKetSk
— Grant Speaks (@GrantSpeaks1) September 22, 2025
All in all, it was an awkward moment in which Portnoy confused Olsen for one of his lackey employees who will roll over for a berating belly rub when he steps to them. That was very much not the case.