Bill Simmons Is Still the Podfather — But Is He Starting to Lose His Grip on the Game?

Last week, I was standing in line at a Dunkin’ in Cambridge when I overheard two college kids arguing about whether Bill Simmons was still “relevant.” One goes,

“He just talks about the Celtics and The Godfather. I’m out.”

And honestly? I couldn’t help but laugh. Because they’re not totally wrong.

Let’s be real — Bill Simmons did change the sports media game.
He’s the guy who made it okay to write 5,000 words on basketball and pop culture in the same breath. But in 2025, media’s different. Everyone’s on TikTok, everyone’s podcasting, and attention spans are shot. So the big question is:

Can the OG sports podfather still hang?

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 From ESPN to Spotify: The Simmons Era

Before podcasts were cool, Simmons was already ranting into a mic — with stats, obscure 2003 Celtics references, and deep dives into The Wire. Here’s a quick breakdown of his glow-up:

• Page 2 at ESPN: Changed how sports columns were written — made them fun, ranty, personal.

• Grantland (2011): A mix of elite journalism and Simmons-y pop culture tangents. It was beloved… until ESPN shut it down.

• The Ringer (2016): He built his own empire. Sold it to Spotify for nearly $200 million.

• Now? He’s got one of the biggest sports podcasts in the world.

But even legends have to evolve. And lately, some folks feel like Simmons is… stuck.

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 What People Are Saying (And Tweeting)

In Reddit threads, Twitter/X spaces, and NBA group chats, you’ll see this a lot:

• “He only talks about Boston.”

• “He still thinks it’s 2008.”

• “Dude is allergic to the WNBA.”

• “Does he know Shai Gilgeous-Alexander exists?”

That’s harsh, sure. But also kinda fair.

Especially when younger podcasters — like JJ Redick, Pablo Torre, or even TikTok creators like Kenny Beecham — are bringing fresher takes and reaching audiences that didn’t grow up with Larry Bird posters.

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 The Vibe Shift: Less Edge, More Echo?

Back in the Grantland days, Simmons was unpredictable — smart, nerdy, emotional. Now? Some say it’s too much “groupthink” with his inner circle guests like House and Russillo. Same jokes. Same takes. Same Celtics tears.

In LA or New York, where younger sports fans binge Woj bombs and TikTok hot takes, Simmons isn’t always hitting like he used to.

Pro tip: If your takes are always “Tatum is the next great one,” you might be losing the room outside of Boston.

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 Why Simmons Still Matters (And Might Not Be Done Yet)

Let’s not forget — the man built the template. Longform content. Podcast networks. The “hangout” pod format. All of it. Simmons made space for all these other voices.

And when he wants to lock in? He still delivers.
His recent episodes breaking down the NBA Play-In drama or tearing apart bad movie sequels? Still gold.

So yeah, maybe he’s not the trendiest voice anymore. But he’s still one of the most influential.

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 If You’re a Podcaster, Creator, or Just a Fan — What to Learn from Simmons

Here’s what Simmons still gets right (and where he could adapt):

 What He Nails:

• Tells stories like a fan, not a stat robot.

• Isn’t afraid to feel something about sports.

• Built loyal community (even if it’s mostly guys named Mike from Boston).

 Where He’s Slipping:

• Needs fresher, more diverse guests.

• Less nostalgia, more now.

• Embrace younger voices without sounding like the “cool dad.”

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Final Take

Bill Simmons may not be everyone’s go-to anymore, especially not if you’re 22 and only watch NBA highlights on YouTube Shorts. But he’s still a force. Still a blueprint.

Just don’t expect him to care what TikTok thinks.
He’s gonna keep talking Celtics, rom-coms, and NFL tiers — and honestly? That’s kind of the charm.

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