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  2. Jon Gruden & Dave Portnoy Watch NFL Sunday With Potential Grinders

    Jon Gruden & Dave Portnoy Watch NFL Sunday With Potential Grinders

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  3. Tossing Coach Jon Gruden A Caesar Salad | What's For Lunch

    Tossing Coach Jon Gruden A Caesar Salad | What's For Lunch

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  5. Dave Portnoy & Ziti vs. Jon Gruden & Grinders | Match 11, Season 5 - The Dozen Trivia League

    Dave Portnoy & Ziti vs. Jon Gruden & Grinders | Match 11, Season 5 - The Dozen Trivia League

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  6. The Yak vs. Jon Gruden & the Grinders | Match 18, Season 5 - The Dozen Trivia League

    The Yak vs. Jon Gruden & the Grinders | Match 18, Season 5 - The Dozen Trivia League

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  7. Dave Portnoy and Big Cat Welcome Jon Gruden to Barstool | Pro Football Football Show Week 11

    Dave Portnoy and Big Cat Welcome Jon Gruden to Barstool | Pro Football Football Show Week 11

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  8. Jon Gruden Joins Big Cat and Co to Sweat Out Denver vs Los Angeles | Barstool Gambling Cave

    Jon Gruden Joins Big Cat and Co to Sweat Out Denver vs Los Angeles | Barstool Gambling Cave

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  12. Jon Dowling & Derek Johnson Discuss Trumps Tariffs, Military Intel & Wealth Transfer April 2025

    Jon Dowling & Derek Johnson Discuss Trumps Tariffs, Military Intel & Wealth Transfer April 2025

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  13. Jon Gruden and Dave Portnoy Join Max and PFT For Eagles-Commanders

    Jon Gruden and Dave Portnoy Join Max and PFT For Eagles-Commanders

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  14. Jon Dowling & Dave Mahoney Financial Updates For April 2025

    Jon Dowling & Dave Mahoney Financial Updates For April 2025

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  15. Jon Dowling & SG Anon Discuss Latest Financial Updates Regarding The Great Wealth Transfer

    Jon Dowling & SG Anon Discuss Latest Financial Updates Regarding The Great Wealth Transfer

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  17. Jon Dowling & Joe Williams Truth Bombs & Financial Updates April 2025

    Jon Dowling & Joe Williams Truth Bombs & Financial Updates April 2025

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  18. Jon Gruden Runs a Tight Ship for Barstool's Flag Football Team | The Yak 12-19-24

    Jon Gruden Runs a Tight Ship for Barstool's Flag Football Team | The Yak 12-19-24

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  21. Jon Gruden Gives Everyone Football Grades on His First Day at Barstool | The Yak 11-14-24

    Jon Gruden Gives Everyone Football Grades on His First Day at Barstool | The Yak 11-14-24

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  22. JON GRUDEN IS A BARSTOOL EMPLOYEE IN THE NEW STUDIO + EAGLES DOMINATE COMMANDERS ON PRIMETIME

    JON GRUDEN IS A BARSTOOL EMPLOYEE IN THE NEW STUDIO + EAGLES DOMINATE COMMANDERS ON PRIMETIME

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