Colin Sheridan: The end of Simmons and Russillo marks the end of something rare and oddly comforting in sports media

END OF AN ERA: The Simmons-Russillo bromance was one of the last authentic buddy dynamics in a media landscape increasingly dominated by algorithm-friendly duos assembled in corporate boardrooms.
There comes a time in every great bromance when the music stops, the lights come up, and the two lads who once shared a microphone and a man-crush must part ways. For Bill Simmons and Ryen Russillo, that moment has arrived. Russillo, the former ESPN stalwart and longtime podcasting sidekick of Simmons at The Ringer, has reportedly decamped for Barstool Sports, a move that feels less like a career step forward and more like the inevitable mid-life crisis purchase of a lime-green jet ski.
It’s not that Barstool is short on followers. Quite the opposite. It is the pints-in-plastic-cups behemoth of sports media, a cultural phenomenon built on the pillars of loud takes, unsubtle-misogyny, and the sort of comedy that plays well in the car park of an American football tailgate. But if The Ringer was the slightly-too-cool Brooklyn bar serving craft IPAs with ironic names, Barstool is the sticky-floored nightclub off the roundabout where the bouncer calls you “chief.” Russillo’s move, then, isn’t just a career move - it’s a vibe shift. And it says something, not only about the direction of sports media, but also about Russillo himself.