Wake Up Barstool may not be a ratings juggernaut yet, but it did at least produce one viral, funny moment earlier this week between Dave Portnoy and Fox NFL analyst Greg Olsen.
It happened on the Monday show hosted by Portnoy where Olsen and Barstool’s own Jon Gruden were present for a segment. And it began with the Barstool head honcho ripping into Olsen’s outfit, saying that he looked like a third base umpire with a plain hat and collared shirt. Was Rob Lowe’s famous NFL hat not available?
Olsen then hit back at Portnoy for his own looks and fashion choices and said that he could skip the show in the future. It even had another Wake Up Barstool host, T-Bob Hebert, asking if it was real or just a bit.
Yall think Greg was actually mad here or just a bit? https://t.co/NDr88fC1W4
— T-Bob Hebert (@TBob53) September 22, 2025
Thankfully, there is no real life bad blood between Greg Olsen and Dave Portnoy. Both took to social media to share that they were in on the joke and that the they have been longtime friends.
Internet, Dave and I have known each other for almost 20 years. We make fun. We banter. We agree to disagree at times
We are all good!!! I’m currently trying to figure a way to be on @wakeupbarstool next week as I fly home from Dublin!! https://t.co/vyM8P8jnbc
— Greg Olsen (@gregolsen88) September 24, 2025
“For record Greg is an absolute OG stole and is in on every joke. Hes the best. He also may have been mad but you can bust his balls about anything,” Portnoy said.
“Internet, Dave and I have known each other for almost 20 years. We make fun. We banter. We agree to disagree at times We are all good!!! I’m currently trying to figure a way to be on @wakeupbarstool next week as I fly home from Dublin!!,” Olsen responded.
See America, it doesn’t always have to always be about drama, negativity, and feuds all the time. Sometimes two friends just want to go on national television and bust each other up about their pathetic attempts to look halfway decent. Although I would want to be 10000% sure it would be cool before attempting something like that with Jon Gruden.

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