Ryen Russillo leaving The Ringer, headed for Dave Portnoy, Barstool-backed venture

Sports media free agency is heating up. Ryen Russillo, one of Bill Simmons’ most reliable sidekicks at The Ringer, is leaving to launch his own digital production company, with Barstool Sports expected to play a major role in the move.

According to Ryan Glasspiegel at Front Office Sports, Dave Portnoy and Barstool are set to invest in Russillo’s new venture, which will reportedly cover everything from distribution and monetization to merch and infrastructure.

In other words, Barstool gets the business machine running while Ryen Russillo gets to build his own brand outside of The Ringer umbrella.

Ryen Russillo leaving The Ringer, headed for Dave Portnoy, Barstool-backed venture

I will not confirm or deny this report. But gun to head I’d probably confirm it

Ryen Russillo Leaving Ringer, Dave Portnoy Expected to Invest in New Business – https://t.co/0qOE60Jqso via @FOS

— Dave Portnoy (@stoolpresidente) August 28, 2025

The Timeline

Russillo’s contract with The Ringer expires later this year. Once it’s up, he’ll officially launch the new company and debut his show under the Barstool-backed setup.

Ryen Russillo Resume

Russillo, 50, has been in the national sports media game for nearly two decades. He broke through at ESPN in 2006, eventually landing his own radio show and becoming one of the network’s more recognizable voices.

In 2019, he left ESPN for The Ringer, where he’s hosted his own podcast while also becoming a staple on The Bill Simmons Podcast. His dynamic with Simmons is often cited as one of the best things The Ringer has going.

Personally, I hate the Boston rats at The Ringer, but there’s no denying the success and talent that has come out of it, unfortunately.

For The Ringer, losing Russillo is a blow. He’s been one of their strongest and most versatile personalities. For Barstool, though, it’s another big fish reeled in as they continue adding major names to their media roster.

Dave Portnoy has been building out the next generation of Barstool content, and Russillo brings immediate credibility with mainstream audiences who maybe wouldn’t normally dip into Barstool programming.

Ryen Russillo leaving Simmons for Portnoy is one of the biggest sports media trades in recent memory. He gets creative freedom, Barstool gets a proven voice with a loyal following, and The Ringer loses one of their most consistent performers.

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