Bill Simmons may have stopped writing with any regularity in the mid-2010s – he claims his fingers don’t work – but that won’t stop him from reminding you of his greatest hits. On a recent podcast about Russell Westbrook’s retirement , he couldn’t stop quoting his old columns. He first referenced an article from the 2012 NBA finals, and wasn’t finished until 11 minutes into the podcast. His guest, The Ringer contributor Kirk Goldsberry, deserved an award for patience. But the biggest blight on the episode came later, in the form of a bizarre ad read.
“This episode,” Simmons announced, “is brought to you by ChatGPT, the Bill Simmons Podcast AI sponsor.” (Emphasis mine; his overenthusiastic delivery mandates the italics.) Simmons said that he had asked ChatGPT what Westbrook’s defining game was. “That was a pretty good answer,” he said of ChatGPT’s offerings, as if it were a precocious, loveable nephew, before encouraging his listeners to try the platform.
Related: As ESPN cuts familiar faces, its retreat from serious NBA coverage is complete
The segment was instructive, not for its content but for Simmons’s ignorance of how he would be perceived. As large language models such as ChatGPT have become ubiquitous, they’ve slashed website traffic across the internet , accelerating the decay of already imperiled media and creative industries. As the founder of The Ringer, a website and podcast network, Simmons should want to protect his company from those effects. It’s a strange look for someone who has historically sought out and promoted unique writing to suddenly trumpet the virtues of an LLM, and naturally raises questions. Is Simmons clueless about how the move is a betrayal of the industry – or does he not care?
Unfortunately, Simmons is far from unique here. Countless podcasts promote AI, from the Joe Rogan Experience to This American Life . Wondery’s The Lead: Starting Five even debuted an AI host in 2023. What makes Simmons’s embrace of it particularly frustrating is that he used to champion human creativity.
In 2011, Simmons founded Grantland under the ESPN umbrella. It rapidly became a dream platform for young writers. Simmons and his editors sought out writers across a variety of beats and writing styles, and encouraged them to do the most ambitious work possible, all funded by ESPN’s deep pockets. The results were often startling for their scope , style , and ambition. Providing the platform for such pieces is a significant part of Simmons’s legacy, and established him as an expert scout of talent on top of being a popular writer. At its best, Grantland was a place that held creativity as sacred, granting writers the trust to follow their stories to the ends of the Earth , or to many thousands of words. Grantland had a spirit opposite to the voicelessness of ChatGPT. It was the exact spirit that LLMs are helping erode from the internet.
Simmons’s own writing – and podcasting – always tended towards the irreverent, from deep dives into basketball history to bizarre pornography references. But even those who didn’t like his work had to concede he had a defined and influential voice. So it makes sense that r/billsimmons , the alarmingly parasocial Reddit community of Simmons fans, reacted so negatively to his first ChatGPT-sponsored episode that the website Awful Announcing ran a story about it .
It’s not just his partnership with ChatGPT that signals Simmons’s move away from a promoter of excellent writing, though. The Spotify-owned Ringer has heavy focus on podcasts. The Ringer puts out an article or three per day – a strikingly low output that undersells the wealth of writing talent that remains on staff. (Twenty-five people on its masthead are labeled as “staff writer”.) The Ringer’s biggest names are best known as podcast hosts and personalities rather than editors and bosses. (Mallory Rubin, director of content at The Ringer but more famous as a podcaster, recently threw out the first pitch at a Baltimore Orioles game.)
And while there are still excellent writers at The Ringer, they don’t always stick around. Claire McNear (whose story about former would-be Jeopardy! host Mike Richards ensured he didn’t get the job) and Miles Surrey (who wrote more prolifically than anybody else on staff) were laid off recently. Then there’s the content itself. While Grantland had dedicated coverage for sports from baseball to boxing, the lone leagues The Ringer covers consistently via the written word are the NBA and the NFL.
There are concerns, too, about Simmons as a boss. Before the sale to Spotify, employees say they were largely kept in the dark about the deal; there have been allegations he took steps to marginalize The Ringer’s union and numerous complaints of low pay at a publication with plenty of revenue. That’s before we get to his recent admissions that he doesn’t wear a seatbelt or the fact that he is under scrutiny for proxy betting .
Media is a constantly mutating industry, necessitating constant evolution to stave off death. Still, if any place is capable of resisting trends to focus entirely on quality, it should be The Ringer. Spotify – a humongously popular and wealthy music streaming service – bought it for about $200m. (Simmons tweeted at the time: “More details to come down the road... but @ringer will remain @ringer in every respect. They appreciate what we do and they want us to be us.”) With Spotify commanding as much money as it does, the slow abandonment of writing is hard to justify.
Meanwhile, Simmons’s promotion of AI suggests that he’s no longer concerned with quality in the way his reputation would have you believe. On a March episode of The Rewatchables , when Simmons announced, “Roger Ebert sadly passed away in 2013,” his co-hosts knew what was coming. Simmons quoted ChatGPT’s take on how Ebert would have reviewed The Nice Guys. Co-hosts Chris Ryan and Rob Mahoney expressed disapproval, but it’s always hard to tell how much of podcast material is banter, particularly when you’re sitting alongside your boss. So let’s turn instead to a recent episode of Talk Easy, in which two senior Ringer staffers, Sean Fennessey and Amanda Dobbins, were asked about Simmons’s use of AI by host Sam Fragoso.
Fennessey and Dobbins immediately stressed that it had been Simmons trying to mimic Ebert through ChatGPT, not them. “I wouldn’t do that,” Fennessey said, adding that he and Ryan had told Simmons about their distaste for the segment. Dobbins claimed not to know that ChatGPT had been sponsoring Simmons’s podcast, and said she’d never used AI before. If lower-level Ringer employees share Fennessey’s and Dobbins’s feelings on the ChatGPT ad reads, they almost certainly do not feel comfortable expressing that disapproval, or the same proximity to Simmons.
You can trace Simmons’s history as a scribe right through that Westbrook podcast: once a writer himself and still evidently proud enough of his body of work to relentlessly quote decade-old material, now willing to advertise a platform accelerating the demise of the profession. Simmons got to spend his entire writing career in an industry mostly free of existential threats. Now it seems like he doesn’t much care if anybody else gets that luxury again, including his own employees.
The tragedy here is not of a once-energetic writer lapsing into lazy podcasting. It’s that employees at a well-funded outlet like The Ringer, which is run by someone with a history of rewarding ambitious writing, have to worry about layoffs and the fact that Simmons is promoting a technology eroding their profession.
As with so many media stories, it did not have to be this way. When Grantland launched in June 2011, Simmons wrote an introductory piece , briefly describing what the website would look like, while reminiscing on his days as a writer on Jimmy Kimmel’s show. Two lines stand out. The first: “I was born to write columns.” That didn’t age so well. The other: “Writing is a fundamentally lonely thing. It’s just you and a blank Microsoft Word document. The process can drive people crazy. (And has.)”
That line aged beautifully. Simmons’s career as a writer and boss has not.
“This episode,” Simmons announced, “is brought to you by ChatGPT, the Bill Simmons Podcast AI sponsor.” (Emphasis mine; his overenthusiastic delivery mandates the italics.) Simmons said that he had asked ChatGPT what Westbrook’s defining game was. “That was a pretty good answer,” he said of ChatGPT’s offerings, as if it were a precocious, loveable nephew, before encouraging his listeners to try the platform.
This report is published with credit to theguardian.com. Full available text from the wire is above. Read on theguardian.com →
Source: theguardian.com · Owen Lewis. Published 3 Sept 2026, 10:00 am.
