Bill Simmons was re-apexing, but he’s now experiencing one of the top seven falloffs of all time. The sports columnist turned media empire empresario has had a hell of a week, catching flak first from his own colleagues for his adoption of artificial intelligence—first as a bit and then as a sponsor—and from regulators for openly discussing proxy betting. But all of Bill’s problems stem from the same starting place: his uncritical allyship with tech companies.
Simmons has, to his credit and certainly to his benefit, always been ahead of the curve on tech adoption. People call him the Podfather because he was one of the earliest people to popularize podcasting back in 2007, and he’s still at it nearly 20 years later. He was blogging in the ’90s, which got him noticed by ESPN. He got Grantland, the prestige publication he launched under ESPN’s header, to make content for YouTube before the platform was a part of every media company’s strategy. After his exit from ESPN, he launched a new media operation called The Ringer that focused heavily on podcasts, almost out of spite because he felt ESPN never understood the value of the medium.
Unfortunately, it seems he may have taken the wrong lesson from being on the cutting edge. Blogs, podcasts, and YouTube are all distribution methods for content. And Bill, for all his warts, makes damn good content. There just aren’t a lot of people out there telling stories about how they were in the middle of a colonoscopy when one of the most important players on their favorite team got traded.
Artificial intelligence does not make good content. It makes, almost by necessity because of how the technology works, derivative content. Simmons has tried to play with that. On his movie podcast “The Rewatchables,” where he and a rotating cast of guests talk about movies that they watch over and over again, he started using ChatGPT to generate reviews in the style of Roger Ebert for movies that came out after his passing.
The ChatGPT Ebert thing is a bit more than a true embrace of the technology, but his co-hosts almost always greet the segment with a cringe you can hear through your headphones and try to hurry him along, clearly uncomfortable with the concept, even as a joke.
One fan of the segment, though, seems to be OpenAI. The company behind ChatGPT became a sponsor of Simmons’ podcast network earlier this year. The hosts of The Ringer’s other flagship film podcast, The Big Picture, are not fans. During an appearance on “Talk Easy” with Sam Fragoso, Sean Fennessey and Amanda Dobbins expressed dismay (and, in Dobbins’s case, shock) when confronted with The Ringer’s dealings with the AI firm.
The Big Picture host Amanda Dobbins appears shocked that Bill Simmons is sponsored by ChatGBT
Sean Fennessey later says he doesn’t approve of Bill’s ChatGBT-Ebert
From the latest @TalkEasyPod pic.twitter.com/JImHnfoeGO
— The r/BillSimmons Podcast (@rBillSimmonsPod) August 30, 2026
Simmons also managed to get himself into hot water by admitting to proxy betting on his podcast. During an episode of “The Bill Simmons Podcast,” the host said that he asked his daughter’s boyfriend to make bets for him on FanDuel—a request he had to make because FanDuel’s sportsbook is illegal in California, where Bill lives, but not in Massachusetts, where his daughter and her boyfriend live. Proxy betting is illegal, and the admission—for which Simmons seemed blissfully unaware would cause him any trouble—resulted in the Massachusetts Gaming Commission opening an investigation into the situation.
FanDuel is, of course, a major sponsor of The Ringer. FanDuel advertisements regularly run during ad breaks; just about anything sports-related covered on The Ringer comes with odds presented by FanDuel, and Simmons regularly talks about trying to get FanDuel to create special bets for his audience.
It’s notable that much of these matters have occurred after Spotify purchased The Ringer in 2020. On its face, this is the exact kind of deal that would make sense both for The Ringer and for Simmons’ better instincts. Getting sucked up by the biggest audio streaming platform in the world is a good fit for a podcast company, and it’d presumably give The Ringer more resources to do what it does best.
Except Spotify doesn’t seem to realize that it’s an audio streaming company. It has increasingly pushed for video content in recent years—a decree that reached The Ringer and turned its podcast operation into a video podcast operation. And last year, the company entered an agreement to distribute its video podcasts on Netflix, meaning The Ringer podcasts went from something that could be recorded with a couple of microphones in a closet to something that requires makeup and a dedicated studio to make—not to mention the fact that The Big Picture’s hosts now find themselves compromised because they have to cover and review films produced by the same company that distributes their content.
Simmons is a Mount Rushmore figure for digital media. But he doesn’t seem to realize that the internet has changed. It seems he viewed Spotify, Netflix, and OpenAI as tools to stay independent—same as his blog and his podcast—so he’d never find himself working under a big boss again as he did at ESPN. What he missed is that they have more control than a boss. They own and operate the biggest avenues for distribution, and he’s surrendered himself and his company to them. It’s harder to quit that than it is to quit a job.
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