Bill Simmons Is Selling ChatGPT to His Listeners. His Writers Should Be Angry.

Key points

• Bill Simmons, founder of sports media outlets The Ringer and Grantland, has become a paid ChatGPT sponsor on his podcast.
• Simmons used a recent episode to encourage listeners to ask ChatGPT sports questions, praising its answers on air.
• ChatGPT is a large language model, the same technology behind AI chatbots that generate text in seconds, trained partly on the kind of sports writing that built Simmons's reputation.
• Critics, including The Guardian, argue the endorsement contradicts the spirit of a brand built on celebrating human writers.
• The Ringer employs staff writers whose livelihoods depend on readers choosing human work over automated alternatives.

Bill Simmons built two of the most celebrated sports media companies of the last twenty years, Grantland and The Ringer, on a single premise: good writing matters. He found writers, developed them, gave them space, and asked readers to care about the craft.

So his latest podcast sponsorship is worth pausing on.

What did Simmons actually say?

On a recent episode about NBA point guard Russell Westbrook's retirement, Simmons announced that the show's sponsor was ChatGPT, a large language model, meaning software that generates human-sounding text by predicting words from patterns in vast amounts of existing writing.

He told listeners he had asked ChatGPT to name Westbrook's defining game. He called the answer "pretty good," speaking about the chatbot the way you might talk about a clever kid, and encouraged his audience to try it themselves.

The ad sat awkwardly alongside a podcast that had already featured Simmons spending eleven minutes quoting his own old columns from 2012.

Why does the sponsorship matter?

It matters because of who is paying for it and who might pay the price.

ChatGPT is made by OpenAI, a company whose tools are already used by publishers to generate articles at scale, cutting the number of staff writers they need to employ. The Ringer, the company Simmons runs, employs those kinds of writers. His guest on the Westbrook episode, Kirk Goldsberry, is one of them.

Simmons built his reputation by arguing that sports deserved the same careful, personal, voice-driven writing as any other subject. That argument is hard to square with an ad encouraging fans to replace that writing with a text generator.

The tension is not hypothetical. Sports media has shed jobs steadily for a decade. AI text tools are one reason publishers give for cutting further.

What should listeners make of this?

Podcast ad reads are normal. Hosts sell mattresses, VPNs, and meal kits without anyone raising an eyebrow. This one is different only because of the specific mismatch between what Simmons has always said he stands for and what he is now promoting.

Listeners who enjoy The Ringer's writing are not obliged to try ChatGPT just because Simmons thinks the answer about Westbrook was pretty good. Reading the actual writers on the site remains an option.

For anyone curious about how these tools work, it is worth knowing that the fluency ChatGPT displays when answering sports questions comes from processing enormous amounts of sports writing, including, in all likelihood, the kind that writers like those at The Ringer produce.

Simmons has said his fingers no longer work well enough to write regularly. That is genuinely unfortunate. But it does not quite explain why the solution he is pointing his audience toward is one that risks making the job harder for the writers who still can.

Common questions

Does a podcast sponsorship mean Simmons is using ChatGPT to write his content?

Not necessarily. Paid sponsorship means a company pays to be mentioned on air; it does not mean the host uses the product to produce their work. There is no public evidence that Simmons uses ChatGPT to write scripts or show notes.

Are AI tools actually taking sports writing jobs?

Yes, in documented cases. Several publishers have used AI tools to generate sports recaps and news briefs, reducing the number of freelance and staff writers they commission. The broader displacement is real, though its scale varies by outlet.