Barstool Sports personality and former NFL head coach Jon Gruden posted a hilarious video of his epic taxi ride through downtown Chicago, alongside colleague Jake Malasek.

Jon Gruden has been out of NFL coaching for four years, having resigned from the Las Vegas Raiders in the midst of the 2021 season after old emails were leaked of him using racist, homophobic and misogynistic language.

Gruden spent the 2023 season as a consultant for the New Orleans Saints to help with his former Raiders quarterback, Derek Carr. Last November, “Chuckie” signed a deal to join Barstool Sports.

Jon Gruden has a wide following on social media and his YouTube channel, thanks to his loud and outgoing persona. So, who else but Chuckie to post a random but entertaining video of his ride in a Chicago taxi?

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