Bill Simmons: A Begrudging Appreciation

Love him or hate him, now that the Sports Guy is out at ESPN, there's no denying the impact he made

Bill Simmons' tumultuous tenure at ESPN has come to an end. Credit: Rob Loud/Getty

In some small part, I owe my career to Bill Simmons. Not in the sense that many professional sportswriters will tell you – that Simmons pioneered a style of writing for peers and fans that no one had seen before, which seems like an odd assertion if you went to college in the 1980s or 1990s and read a single zine dedicated to anything. 

No, despite writing about 400 longish blog posts and occasionally getting an "attaboy" from pro sportswriters, what finally got editors to utter the magical phrase "we would like to give you some money" was something I wrote over a couple of beers, hit publish on and went to sleep. Bill Simmons was about to launch Grantland, a vanity website about sports and culture, and I looked at him and at the site's soft launch and said, "Bill Simmons sucks, and so will this."

Five years later, Simmons is gone. ESPN president John Skipper announced that negotiations have failed, and his contract will not be renewed. In the meantime, I got to be wrong many times over. Not just wrong, but delightfully so, from a site whose depth of contributors not only surprised almost all the critics but won them over. And if Skipper wants to be true to the wording of his official statement, he should keep surprising critics like me for years to come.

Like a lot of people, I really enjoyed Simmons for about a year. Then I started noticing a lot of catchphrase and self-branding repetition (like the Ewing Theory) and enjoyed him less. His everyman pose grew from an affectation to an insult as he started playing video games with Tiger Woods, (almost) clubbing with Manny Ramirez and getting great seats to any sporting event that interested him. His updates grew infrequent and more reliant on gimmicks. Whole sea changes in sports went unacknowledged until they had a direct impact on his life (Sabermetrics famously only became relevant when someone kicked his butt in fantasy baseball by drafting Ben Zobrist), an unforgivable solipsism for someone styled as a fanalyst.

From a social standpoint, the bro-targeted enthusiasms got more grating the further I got from age 21. Having MTV's Road Rules as your cultural barometer is really weird when you're old enough to drive and get out of the house and drink and think about anything else. Likening NBA stars to 1980s TV actresses' long-term fuckability is either shallow or gross, and The Book of Basketball is simultaneously one of the most thoughtful fan histories and the most brain-dead misogynist high-five anthology I've read. But there was a large market for this – sports fandom is still pretty sexually unevolved, which is why every comment section's go-to insult is to liken someone to a woman or her parts – and one got the sense that this would never change.

So, at the time, a sports-and-culture website from Bill Simmons looked to fare about as well as, to borrow one of his oft-repeated references, a new movie "from the demented mind of Danny DeVito." It's not that there was anything wrong with the project; you just wanted almost anyone else at the helm. The site famously hired human Thought Catalog archive Chuck Klosterman, along with Dave Eggers – the latter penning this blowjob of Wrigley Field before disappearing in a puff of meta-reflection. The soft launch didn't help much. Katie Baker's Knicks piece could have run as a feature on any sports site in the English-speaking world, and seemed like the sort of thing that got roped into the Simmons orbit simply because he could say gimme. Molly Lambert, whose default offerings ever since veer from the "merely" thoughtful to the excellent, penned a summer movie preview that in retrospect reads more like a junior writer knuckling under to an editor's bad idea.

Then came the launch: Chuck Klosterman on a junior-college basketball game he saw; legendary Bourbon Bastard and under-acclaimed craftsperson Chris Jones getting the lede of his first column, about the date he lost his virginity, wrong; Wright Thompson writerly writing about a place writers drank and talked about writing. It looked for a while there like the site would be a hater's turkey shoot at slow-moving targets grown bloated from too long at the banquet table of the Writers' Self-Suck Society, where the first step in the initiation is to change your Twitter bio to, "Raconteur, flâneur, globetrotter, life-quaffer, collector of life stories. New book 'Mal Aria: How One Man Lived Three Weeks on an Airboat in a Swamp' out by HarperCollins." 

Then all that changed. While at the end of 2011, Deadspin could still put out this kind of list, by the end of 2012, enough haters had been forced to post a link to a Grantland piece and say some variation on, "Damn, this is great." By the end of 2013, there was no question that the site had exceeded critics' expectations and may even have lived up to the grandiose pronouncements of its own.

So what changed? In a longer reply truncated in this Rolling Stone piece by Rob Tannenbaum, Deadspin's then editor-in-chief Tommy Craggs wrote:

"Grantland, for all its faults, pays real money for writers I like a great deal to write about the things that interest them. It turns out Simmons has better, more catholic tastes than his own writing would suggest, which is the best thing you could ever say about an editor-in-chief..."

That's a great explanation, in a pinch, but there are two more things worth considering:

One, that after a launch in which it seemed like Simmons was trying to create an all-star team of writers, a lot of those big names have fallen away. Eggers, most dramatically; Klosterman hasn't written in over a year; Jones left; Wright Thompson last appeared in 2012. Instead, Grantland let a lot of other voices develop without hewing to either Simmons' interests or that universal A Writer Is Writing voice that seeps into most longform journalism like Sam Shepard reading the promotional materials from a craft distiller specializing in brown liquor. 

Instead of paying people for the resumes they already had, Grantland has done an admirable job of paying to create resumes many writers would like to have. Molly Lambert has been practically a workhorse for the site. The Masked Man David Shoemaker, already one of the best wrestling writers when he joined, has been given ESPN's brand strength to conduct long interviews with people like WWE's booker and multi-time champion Triple H. Alex Pappademas got to hit the road with Dan Harmon. Brian Phillips consistently writes some of the most literary and insightful sports analysis around. Holly Anderson brought the comic sensibilities of Every Day Should Be Saturday to a site that could have been dangerously self-serious about college football. Rembert Browne interviewed the president! The list isn't endless, but probably neither is your patience.

Two, maybe Simmons just grew up a little more. After a Grantland article outed a trans woman who later committed suicide, Simmons offered an apology that was much more mature than a lot of people might have expected from him just five years before, and he gave transgender sportswriter Christina Kahrl a space on the site to state, explicitly, "What Grantland Got Wrong." And before that, the notoriously thin-skinned Simmons set one of his petty beefs aside and hired the outstanding Charlie Pierce to write for the site.

But now Simmons is gone, and the split has been coming for a while. Whatever else you might think of him, he was an extremely powerful empire within a corporate entity that doesn't seem long on tolerance for competing power structures. Maybe Simmons was done evolving as a dude and as a writer. It's hard not to get that sense from listening to his default jokes on his podcast and reading similar approaches in his rare columns. And maybe Grantland's evolution owes more to his having the wit to stand aside and let editors he respected guide the careers of writers they had faith in. Whatever it was, we should thank him for coming that far. And, besides, he's going to be fine. By this time next year, someone at Fox or NBC or some vulture capitalist will have overpaid for his services. 

That still leaves Grantland.

At the end of his statement regarding Simmons, ESPN president John Skipper added, "ESPN remains committed to Grantland and we have a strong team in place." Moreover, as he told the New York Times' Richard Sandomir, "It long ago went from being a Bill Simmons site to one that can stand on its own."

We should hope that's true. Grantland's numbers have always been small for its stature and bolstered by the traffic that Simmons brings in. Without him, there's always the chance that writers will be told to get shorter, punchier, less thoughtful, learn less, write more and generally fall prey to the fast-paced endumbening that defines much of online media hunting in the tall grass for virality. Either that, or, without the loudmouthed eponymous presenter of "Bill Simmons presents Grantland," it may lose the millions of fans who would push back against its being quietly filleted, leaving it to die in the night, when the majority of contracts come up.

That shouldn't happen, and there's no fiscally responsible excuse for it to ever happen. ESPN employs Skip Bayless, the guy your dad gestures to on the TV screen when he wants to make a race-baiting point without seeming his usual clumsy self about it. They employ Tony Kornheiser, who was last seen visibly trying during the first Bush administration. They employ recent "accidental" domestic violence apologist Mike "Did You Know I'm Friends With Magic Johnson" Wilbon, whose last few journalistic haymakers have been directed downward at people describing his career. They employ Stephen A. Smith, who thinks women need to stop provoking men into domestic violence. They are throwing away ungodly sums of money on a vanity site for Jason Whitlock, who seems delusional to the point of locking all the doors to a house and burning it down with himself and his employees inside so he can use them as his warriors in the afterlife. These people are responsible for millions of dollars ESPN would be better off methodically flushing down a toilet in one of those 10-hour YouTube videos. At least that would go viral for something other than scorn.

ESPN earns billions of dollars annually, and that number is jaw dropping regardless of who is doing the calculating. They then spend that money on multiple personalities who run the gamut from toxic to merely negative-value-added. Losing what amounts to drops in the bucket on a website that has grown to regularly produce excellent journalism should be a no-brainer for a property whose many stars are the definition of the term. If Skipper meant what he said about Simmons' departure not being a factor, we should insist he stick to it and demand that he keep his word in the most high-minded of senses and, failing that, demand that whatever red ink Grantland generates be ESPN's future penance in perpetuity.