Bill Simmons: Always a Step Ahead of ESPN's Old Guard

The news of Bill Simmons leaving NBA Countdown didn’t surprise too many people at ESPN. His departure from the show had been rumored since that awkward moment he had during the NBA Finals with NBA Countdown’s host, Sage Steele.

According to some in Bristol, Simmons had grown tired of his time on the show, and the commitment was a bit much given his website, other projects and family. But make no mistake – the Steele moment was a tipping point. Like previous incidents at ESPN.com and Grantland – which we’ll get to later – Simmons needed an exit strategy, and in speaking with multiple ESPN employees, few thought he had a legitimate one for extricating himself from Countdown.

After what went down on the show in 2013, with Michael Wilbon getting … shoved out, and then taking Magic Johnson with him, it wouldn’t have been a good look for Simmons if he tried to place his choice – Michelle Beadle – in the host chair. Steele is well-liked at the network, smart and not afraid to challenge anyone, plus she had just moved her family across the country to be closer to the show’s set.

Among those I spoke with in Bristol, many expected him to take his ball and go home because he couldn’t get his way.

What gobsmacked everyone was that yet again, Simmons found a way to slither out of a potentially sticky situation: Hey, how about giving me my own NBA TV show, maybe twice a month, where I bring on Grantland writers and we talk hoops? More fun than formal, it’ll incorporate the tone of the site. Brand extension!

And ESPN President John Skipper, always forward-thinking and willing to take some risks – he’s the biggest Simmons advocate at the network – was sold.

Simmons can be buoyantly funny in his columns, but anyone confusing him for the decade-ago “Sports Guy,” full of witty one-liners and pop culture references, isn’t familiar with his work on the political front at ESPN, where he displays the stony countenance of an action hero in doing battle with the suits, who still view him as the Glorified Blogger with the Boss’s Ear.

What many are finally coming to realize is that Simmons has a little Keyser Soze in him – he’s always a step ahead, and just when you think you’ve got him where you want him, boom, he’s out the back door, on to his next project you didn’t see coming.

Take Grantland.

Simmons, who found immense popularity as “The Sports Guy” on ESPN.com, rankled editors who didn’t think he paid his dues and was more fan than Media Member. Annoyed with them – surely you remember the battles – Simmons pulled off a brilliant end-around: He convinced Skipper to give him his own website where he wouldn’t have to put up with the petty political games that can stifle enthusiasm and sap creativity.

And thus Grantland was born, with his own staff of hand-picked talent. A victory for Simmons.

Grantland hasn’t delivered the traffic to back up the massive budget, but it matters not – the site has a we-do-what-we-want feel to it and is now more of a destination for young, promising writers than ESPN.com itself.

The pesky suits in Bristol obsessively nit-picked Grantland for the first couple years – too much Hollywood, not-obscure-enough features, that sort of thing – but mostly they lay in the cut, waiting for an opening to deliver a knockdown punch. They got it January 2014 with the debacle that was Dr. V’s Magic Putter.

As is the case with websites run by a high-profile editor, Simmons took 98 percent of the heat for the disaster, with the other two percent going to ESPN. (Quick, do you remember the author of the story without googling?)

Something had to be done!

Fists met tables in glass offices at HQ. The old school faction in Bristol huddled together as if to say, “we got ‘em.”

Then came another savvy stroke from Simmons to escape the criticism. A few months later, Grantland was branching off into “Exit 31,” taking with him Nate Silver’s 538 (Silver had his crash course in bullshit office politics at the New York Times, no sense in even sticking around for round two of that!) under the aegis of Marie Donoghue. Yes, she was handpicked by Simmons. Fun fact: Donoghue is based out of New York City, not Bristol.

Goodbye, old guard, who seemed to enjoy tinkering with Grantland. Exit 31 was its own shop with its own people (if you want, “new guard”).

If you want to use the phrase, “taking his ball and going home” you can, but Simmons isn’t going home every time he runs into trouble: He’s trading up. And it always seems to work out.

NBA Countdown has always been second fiddle to TNT’s outstanding Inside the NBA, and Simmons knew going in it would be a colossal challenge simply to make the show relevant. How do you even quantify if he accomplished that in the last three years? Ratings? Memorable moments? Reaction to the show on social media? How about this one — has Bill Simmons gotten better on TV to warrant his own 1-hour prime time show?

And yet all of that may not matter. He complained publicly about the lack of time on Countdown’s pregame show (Inside the NBA gets an hour); he complained when the postgame show was condensed or shrunk to a sound byte (Inside the NBA goes on and on and on). And now Simmons is gone, off to captain his own show, where he won’t have to grapple with a challenging host or struggle for air time against outsized personalities.

Don’t think his naysayers at ESPN will go away, though – they’re already whispering about why anyone would watch this show – why isn’t this banished to ESPN2, they ask – and how it won’t sniff the ratings of Countdown because it isn’t wrapped around live programming.

So would it surprise you when Simmons goes out and lands Larry Bird for the first episode and Steve Nash for the second? You know he’s got something cooking on a low simmer.