Bill Simmons weighed in on ESPN’s handling of Max Kellerman in comments to Vanity Fair, calling the network’s approach predictable.
“It’s so rare to find unique, thoughtful sports voices who can thrive as a solo act or with someone else,” Simmons told the outlet in an email. “They completely misunderstood why he’s good, which is par for the course for ESPN, by the way.”
Simmons is right that Kellerman represented something rare. But he’s also building a case he’s been constructing for a decade, using Kellerman as the latest evidence that his former employer doesn’t understand what makes certain voices valuable. And now that Simmons is bringing Kellerman to The Ringer for a podcast with super-agent Rich Paul, he gets to prove he can do something with that talent ESPN couldn’t figure out in 20 years.
Kellerman spent nearly two decades at ESPN across various roles before the network laid him off in 2023. He hosted Around the Horn in the early 2000s. He became one of boxing’s most knowledgeable analysts. He replaced Skip Bayless on First Take in 2016 and spent five years debating Stephen A. Smith before Smith requested his removal in 2021. ESPN moved him to afternoon radio with Keyshawn Johnson and Jay Williams. When they canceled that show as part of broader layoffs, Kellerman’s ESPN run came to an end.
Kellerman largely disappeared after ESPN let him go. Friends in sports media kept hinting his return was imminent, but when Around the Horn ended its run, Kellerman didn’t show up for the celebration. He resurfaced to call boxing for Netflix and later joined a show for Ring Magazine, but he kept quiet about ESPN and how Stephen A. Smith handled pushing him out. That silence held until last week, when he joined Simmons’ podcast and explained what happened. Smith didn’t want to debate someone that sharp every day, and Smith knew being a solo act meant more money when his contract came up.
And that decision to push Kellerman aside reinforces the exact pattern Simmons described to Vanity Fair. ESPN had someone who could do multiple things well, and they used him exclusively as a debate foil until their franchise player no longer wanted him.
What makes Kellerman interesting is his range. He can break down boxing with technical precision, handle debate television, and lead thoughtful conversations about sports and culture. He doesn’t need to yell or manufacture takes.
That doesn’t fit First Take‘s structure, which runs on quick-hit debates designed for social media clips. ESPN wanted Skip Bayless 2.0 — someone delivering contrarian takes for Stephen A. to demolish with theatrical outrage. When Kellerman proved too analytical for that, when he tried to examine topics instead of provoking reactions, the chemistry broke down.
Stephen A. has said he didn’t want to keep working with Kellerman, calling it a chemistry issue while insisting he has no personal animosity toward Kellerman. And yet, he spent 25 minutes responding to Kellerman’s comments on his show, mocking Kellerman’s “Muhammad Kellerman” reference and relitigating his 2016 Tom Brady take.
According to Vanity Fair, Kellerman kept his comments about Smith brief, saying he’d save the whole story for his podcast with Rich Paul. That’s the show Simmons is launching at The Ringer, built around letting Kellerman do what ESPN never really let him do: have substantive conversations about sports and culture without the performance.
This has been Simmons’ pattern since ESPN forced him out. He’s taken talent they didn’t maximize — Ryen Russillo being the obvious example — and attempted to show what happens when you build around their strengths instead of forcing them into formats that don’t fit.
Sometimes it works, sometimes it doesn’t. But every attempt reinforces what Simmons has been saying about ESPN since 2015.