Last week, The New York Times ran a story about Bill Simmons’ especially cringe use of AI and his illegal proxy betting in Massachusetts. 

The gambling story is legitimately breaking news. Simmons’ affinity for AI slop, by contrast, is long-running and has been out in the open for anyone who cares to look. Back in August, a popular comment (upvoted 1,100 times) on r/billsimmons led to an Awful Announcing story diving deeper into Simmons’ AI habit. As the story noted, he was razzed back in March for busting out his iPad during an episode of his movie pod “The Rewatchables,” and quoting ChatGPT’s limp impersonation of Roger Ebert. And on an August episode of “The Ringer Fantasy Football Show,” Simmons apparently threw to the bot to name the defining game of NBA star Russell Westbrook’s career. (This feels especially egregious considering that writer Tyler Parker has his own list of Westbrook highlights right on The Ringer’s website.) 

This icky embrace of ChatGPT may or may not be related to OpenAI’s gratuitous sponsorship of the network. It may also be why Simmons has recently been spotted flaunting an Anduril hat, a fashion choice that’s either clueless or ghoulish, depending on how much credit you give him. Hey, when one of your biggest sponsors is also a high-profile partner of a famously evil military defense company, who’s to say where your head’s at?