The Boston Sports Guy is right at home on HBO.
There’s no sense in pretending that I was on the Bill Simmons train any earlier than anyone else. I wasn’t there when he was writing for The Crusader, the paper of his alma mater Holy Cross. Nor was I reading his work before he was recruited from BostonSportsGuy.com to ESPN in 2001. It wasn’t until years later – even after he published his Book of Basketball — when his star had risen to the point of launching Grantland in 2011, that I discovered the magnetic pull of the Bill Simmons universe.
As a fan of his podcast The B.S. Report (now The Bill Simmons Podcast), it felt like I got to know Bill Simmons on a deeper level than most cultural pundits. He was an unabashed homer for Boston sports, a rebellious figure within the sports entity that had been a staple of my childhood, and a smart publisher to whom I looked up as I was building the website you’re reading now. Most of all, Simmons felt like the kind of guy with whom you could have a beer and talk about anything for hours. That’s his brand, he’s an infinite well of curiosity and conversation.
For years, there’s also been this underlying thought that I couldn’t escape about Simmons’ work. It was at the heart of why he left ESPN. He always seemed to be holding something back. Whether it’s a few curse words here or an unpopular opinion with ESPN brass there, the version of Simmons that made the B.S. Report so popular only seemed to be operating at about 85% freedom at any time. When he stepped beyond that 85% line, he found himself suspended.
When he finally left, Grantland was lost without his stewardship. And though it retained many talented writers, it’s eventual downfall felt inevitable. These were the dark days of Simmons fandom, when it was hard to know what would come next.
Sometime later, HBO swooped in and became an initial investor in The Ringer, one of our digital neighbors here on the Medium Publishing Platform. This gave Simmons The Podcaster a chance to reboot his show in a far less censored environment. It also gave Simmons The Publisher an opportunity to show us that he’s an elite-level talent scout, bringing writers like Mallory Rubin, Juliet Litman, Chris Ryan, Jason Concepcion, Jonathan Tjarks, Sam Donsky, and many others along with him.
But it wasn’t until last night when I realized that Bill Simmons’ media personality had come to full bloom. In the opening episode of his new show, Simmons opened casually with a monologue about Lebron James and the Cleveland Cavaliers. My own followers will note that this plays right to me as a Cavs fan, but there’s more to it. There wasn’t fanfare in the opening of his show, it was just Bill speaking directly to us, getting to the heart of the big pop culture story of the week with precision and charm.
The episode continued to unfold by showing off the best of what Simmons does: getting his guests to let go and speak openly. On his podcast, this is often done with his close friends, other writers, and the occasional celebrity. On Any Given Wednesday, he went mano a mano with Charles Barkley over the attitudes older NBA stars have toward the stars of today, then got Ben Affleck all fired up about the Boston sports scandal Deflategate. There were F-bombs and unfiltered sentiments flying everywhere. It was a master class in keeping it casual while hitting the zeitgeist nail on the head.
With Any Given Wednesday, Simmons has reached a new level. A peak version of what he’s been doing for years. Not a peak in the sense that there’s only one place to go (down), but in that it feels deeply earned after years of holding back to ensure that he didn’t get fired. It was always a joke between he and NBA Countdown co-host Jalen Rose, in which Rose would tell Bill “Don’t get fired” prior to him expressing an opinion on-air. In the comfort of his new home at HBO, Simmons no longer has to worry about getting fired. And the rest of us are reaping the rewards.
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