September 3, 2026, (Inside AI) — Bill Simmons, the founder of The Ringer and Grantland, has begun promoting ChatGPT on his podcast, a move that has sparked criticism from fans and staff alike. The sponsorship deal, announced during a recent episode about Russell Westbrook's retirement, positions the AI tool as a sponsor of The Bill Simmons Podcast.
Simmons used the ad read to share ChatGPT's answer to a question about Westbrook's defining game, calling it "a pretty good answer." The moment drew immediate backlash from the r/billsimmons community on Reddit, with many fans seeing it as a betrayal of the creative spirit that defined Simmons's earlier work.
The partnership is notable because Simmons built his reputation on discovering and developing unique writing voices. In 2011, he founded Grantland under ESPN, a platform that became known for ambitious, long-form journalism and for giving writers the freedom to pursue stories without compromise. That ethos stands in direct contrast to the homogenized output of large language models, which critics say erode the very creative industries Simmons once championed.
Simmons is not alone in embracing AI sponsorships. Podcasts ranging from The Joe Rogan Experience to This American Life have promoted AI tools, and Wondery's The Lead: Starting Five introduced an AI host in 2023. But the frustration with Simmons is more acute because of his history as a talent scout and promoter of human creativity.
From Talent Scout to AI Pitchman
Grantland's legacy includes launching the careers of writers who produced startling, ambitious work across sports and culture. Simmons's own writing was irreverent and influential, with a defined voice that even his critics acknowledged. That voice is now being used to sell a technology that many in media see as a threat to their livelihoods.
The Ringer, which Spotify acquired for about $200 million in 2020, has shifted heavily toward podcasting. The website publishes only a handful of articles per day, despite having 25 staff writers on its masthead. Recent layoffs, including those of Claire McNear and Miles Surrey, have added to concerns about the outlet's commitment to written journalism.
Simmons's use of ChatGPT to mimic Roger Ebert on a March episode of The Rewatchables drew disapproval from co-hosts Chris Ryan and Rob Mahoney. On a later episode of Talk Easy, senior Ringer staffers Sean Fennessey and Amanda Dobbins distanced themselves from the practice. "I wouldn't do that," Fennessey said, adding that he and Ryan had told Simmons about their distaste for the segment.
The Cost of Chasing Trends
Simmons's promotional shift raises questions about his priorities. Employees have previously alleged low pay and a lack of transparency around the Spotify sale. The Ringer's union has also raised concerns about marginalization. These issues, combined with the ChatGPT sponsorship, paint a picture of a leader drifting from the values that made his name.
When Grantland launched, Simmons wrote that he was "born to write columns" and that "writing is a fundamentally lonely thing." Those words now seem distant from a man who spends his podcast quoting old work while advertising a tool that automates the creative process. The tragedy, as many see it, is not that Simmons stopped writing, but that he is now promoting a technology that could make it harder for the next generation of writers to find their voice.
