Barstool Sports is doubling down on the business of Gruden.
On Thursday, Barstool Sports founder Dave Portnoy announced the outlet is hiring former Washington Redskins head coach Jay Gruden to join his brother Jon for a new football show. The brothers Gruden will debut the Gruden Family Football Show this fall.
What is better than 1 Gruden? Two Grudens! Welcome to the family @Coach_JayGruden Look for the Gruden Family Football Show coming this fall @BarstoolGruden
Power moves only
— Dave Portnoy (@stoolpresidente) July 23, 2026
Jay Gruden comes to Barstool with a bit of media experience under his belt. Between April 2024 and May 2025, Gruden hosted a podcast alongside Colt McCoy, AQ Shipley, and Justin Pugh called Clean Pocket for Underdog. The show quietly went away last year and Gruden joined Gilbert Arenas’s football show, The Arena: Gridiron, alongside Skip Bayless and Aqib Talib. That show was also canceled earlier this month, along with Gil’s Arena, after Underdog shut down its original content arm.
Jay’s brother Jon, on the other hand, has carved out a large following and several successful shows since joining Barstool in 2024. Under the Barstool umbrella, Jon Gruden has revived his popular pre-draft quarterback film breakdowns with Gruden’s QB Class. At ESPN, Gruden completed seven seasons of Gruden’s QB Camp between 2011 and 2018 before returning to coaching with the Oakland Raiders. Now, Gruden makes regular appearances on Wake Up Barstool during football season.
While Jay Gruden is still a relative unknown as a media personality, pairing him with his brother should provide the new Barstool show instant credibility and chemistry.
About Drew Lerner
Drew Lerner is a staff writer for Awful Announcing and an aspiring cable subscriber. He previously covered sports media for Sports Media Watch. Future beat writer for the Oasis reunion tour.