Sports Nut

How Bill Simmons Changed Sportswriting

And why being let go by ESPN is the best thing that could have happened for his career.

Time for the next chapter: Sportswriter Bill Simmons speaks at the 2010 New Yorker Festival at DGA Theater on Oct. 2, 2010, in New York City.

Photo illustration by Slate. Photo by Amy Sussman/Getty Images the New Yorker

The first time I read Bill Simmons was in the earliest days of his ESPN tenure; I was a displaced Bostonian living in New York City, and it was a thrilling experience, all that incorrigible homerism splashed up against the gaudy yellow backdrop of the late Page 2. I don’t know how else to start an essay about Bill Simmons other than in the first person, since that’s where he lived, or lives; in the wake of news of Simmons’ impending and apparently involuntary departure from ESPN, it’s already hard not to write about him in the past tense. In the 14 years he spent at ESPN, Bill Simmons transformed himself from an out-in-the-weeds curiosity (“The Sports Guy”) to the most influential sportswriter of his generation. Now he can die in peace, as he’s frequently remarked, even though that’s almost certainly the last thing Simmons is currently planning on doing.

His rise was meteoric and at least partially enabled by circumstance: Simmons’ tenure at ESPN saw the four major Boston sports teams win an astounding nine championships, most memorably the 2004 Boston Red Sox run, which inspired some of the best writing of Simmons’ career, later collected in a New York Times best-selling book. But he also worked, relentlessly hammering out column after column that showed a preternatural grasp of how sportswriting was changing in the digital age, a groundbreaking cocktail of passion, persona, stamina, and approachable eccentricity. “Simmons’ writing is distinguished not by its Olympian distance from sports but by its almost tender intimacy,” wrote Bryan Curtis in a 2005 Slate appreciation. He anticipated the rhythms of an emergent and massively consequential online sports fan culture, and quickly came to set those rhythms himself. Rambling, snarky play-by-plays of draft telecasts, theoretically suspect but absurdly thorough rankings of pro basketball players’ hypothetical trade values—it was impossible to tell if Simmons invented the audiences for these things, or just awakened and united them.

Like most, I was initially shocked by the news of Simmons’ split from ESPN, but it now strikes me as inevitable, necessary, and potentially the best thing to happen to Simmons since January’s Super Bowl, at least. At the crux of the Simmons-ESPN divorce is an issue that’s plagued the Worldwide Leader throughout the writer’s tenure: namely, whether ESPN is in the business of sports journalism, or in the business of promoting the interests it ostensibly covers. There was the 2006 debacle Bonds on Bonds, in which Bonds and his lawyers were given editorial control of an “all-access” documentary series that aired at the height of the slugger’s PED controversy; there was LeBron James’ The Decision, a disastrous one-hour special that sought to alchemize breaking news into corporate synergy; there was the network’s endless hyping of Tim Tebow, which culminated in a bizarre, pro bono infomercial; and, of course, their infamous withdrawal from Frontline’s landmark CTE documentary League of Denial in 2013, a decision widely rumored to have been made under pressure from the NFL.

This last instance is most instructive to Simmons’ current situation. Last fall Simmons was suspended for three weeks by ESPN for calling NFL Commissioner Roger Goodell a liar, then daring his bosses to suspend him for doing so. The surface gloss was that Simmons was punished for biting the hand that feeds him, but he was really suspended for biting the hand that feeds the hand that feeds him: ESPN is in bed with the NFL to the tune of nearly $2 billion per year. News of Simmons’ nonrenewal came on the heels of another anti-Goodell rant, this time on Dan Patrick’s (non-ESPN-affiliated) radio show last Thursday.

Simmons was fired because he refused to subsume his own brand into ESPN’s, which is increasingly indistinguishable from the brands ESPN protects. Simmons has always been a brand first and foremost, and I don’t mean that as a criticism. This is, after all, what most writers are after; we often prefer more polite words like style and voice, but ultimately we’re all out there trying to carve out (and profit from) a space that’s inimitably our own and no one else’s. There’s a reason that Norman Mailer—a headstrong, sports-obsessed, and vaguely Simmons-ish figure in his own right—once titled a collection of his own writing Advertisements for Myself.

Simmons’ brand was always clearer and sometimes crasser than most, the truth-to-power outsider who wrote from a fan’s perspective, a loquacious and opinionated everyman prone to hyper-referential and overly capitalized Ewing Theories, Levels of Losing, Retro Diaries, and movie-quote-themed listicles. At best, his lack of access—and, crucially, lack of deference owed from that access—made him a sort of ersatz Spartacus for a more cynical brand of sports fan, skeptical of establishment narratives and unafraid to splash around in the waters of conspiracy. For a relatively late example of this, see his 2013 column “Daring to Ask the PED Question,” a tormented and probing thought experiment that comes shockingly close to a deconstruction of sports fandom—and Sports Guydom—itself.  

In recent years the quality of Simmons’ column has gotten worse, sometimes to the point of being unreadable. Drew Magary’s takedown in Deadspin this past March, delicately titled “Bill Simmons Is a Name-Dropping Waste,” was both scathing and not entirely unfair. Stretched insanely thin by TV work and other non-writing commitments (his hugely popular podcasts, 30 for 30, Grantland), in his worst moments Simmons has become a lazy writer prone to rehashing gimmicky and uninsightful conceits ad nauseum; an inveterate name-dropper who confuses proximity to famous people with reporting; a self-mythologizer whose columns sometimes read like a Retro Diary™ of Bill Simmons reading his own archive.  

Of course, a lot of the negativity directed at Simmons over the years has always had a tinge of jealousy. His everyman shtick lends itself to the charge that anyone could do what he does, even if no one else ever has. And the fact is that all of the problems in the above paragraph have been enabled by his bosses, if not demanded by them. ESPN is a stardom machine, and as Simmons’ own star grew he became increasingly enmeshed in the ESPN system of celebrity maintenance. In recent years he’s been rubbing elbows with the likes of Jalen Rose, Doug Collins, Magic Johnson, Kobe Bryant. Yeah, Simmons wrote and talked about these friendships too much, but Simmons always wrote and talked too much about his friendships with everyone—this is a guy who’s spun two of his college buddies, JackO and Joe House, into C-list media properties. For ESPN, Simmons’ ex-jock name-dropping wasn’t a problem so much as vertical integration, a sort of snowballing fame game.

It’ll be interesting to see what comes next, and the transition almost certainly won’t be smooth. To pick just one sticking point, Simmons has been the premier NBA writer of the 21st century, and leaving ESPN will surely (and sadly) hamper his access to the league. But getting away from the ESPN machine, the network’s constant and clumsy attempts to superimpose its brand onto his own, might well be the best thing for Bill Simmons the writer, who is better than we’re currently inclined to remember. One of his most rightly celebrated columns is completely un-sports-related, a eulogy for his late dog Daisy, better known as the Dooze. The piece ends thusly:

The day after The Dooze left us, our little boy woke up and my wife carried him downstairs to feed him like she always does. I was still half asleep and could hear her footsteps. Then I heard this: “Day-zee. Day-zee.” That part didn’t make me sad. The part that made me sad happened three mornings later … when my wife was carrying him downstairs again and he didn’t say anything.

That’s awfully good writing. It’s honest, it’s direct, it’s poignant, it fills the heart and breaks it and connects us to each other in doing so. At his best, this is what Bill Simmons did, and might continue to do in a new space—he just needs a change, a push, a “Juvenation Machine,” to borrow from his own capitalized lexicon. I have no idea what that change will look like, which is as it should be: it’s his chapter to write, his weird and singular road to continue. In 14 years at ESPN, Bill Simmons was always a brand of his own, and never a company man. Of a writer there are far worse things to be said.