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Shi: Bill Simmons is leaving ESPN, and for him, nothing any good isn’t hard


In honor of the Bill Simmons attitude to sportswriting, this article is going to be way too long for print, and you’re just going to have to read the rest online.

Bill Simmons is probably the most widely read sportswriter in the country. He’s also about to lose his job.

In just a decade or so, we’ll probably be seeing our first national sportswriters who can say, I got into the business because of Bill Simmons. And yet he’s going to be leaving ESPN. We don’t know where he’ll go next. We don’t know what he’ll do in the meantime.

For people that have grown up reading Simmons, this entire affair is surreal, in large part because we’ve also witnessed his remarkable reinvention over the last several years. He made his name as the Internet version of the person at the bar who could talk your head off about sports while still being chill, and while he’s still that person, he’s much more than that. He’s not “the guy who developed the Ewing Theory” anymore. (If you need to ask, that just proves my point.) He’s the guy that runs sports megawebsite Grantland, reinvented the sports documentary and wrote the most absurdly detailed basketball book of all time.

And soon he will be gone. Grantland was supposed to be the future of sportswriting. Is it big enough to survive losing Simmons? And is Simmons big enough to survive losing Grantland?


Grantland’s current success belies just how much of a question mark it was when it started up four years ago. At first, pretty much everybody thought Grantland was going to be an extension of Bill Simmons’ id. It was a “sports/pop culture” website. What was that even supposed to mean? Nothing at the scale of what Simmons was proposing had ever been done. And at that stage in Simmons’ career, you really couldn’t have been faulted for thinking that Grantland was going to be a circle of twenty people chosen to be just like Simmons, making tortured references to 80s movies nonstop. (Simmons is one of the few people who are actually good at that.) I even heard a rumor that ESPN just gave Simmons Grantland (or the 30 for 30 documentaries) to shut him up about the fact that they were paying Rick Reilly more.

Fast forward to 2015, and Grantland’s the best pure sportswriting website in the business. The only part of Simmons’ attitude that he imposed on the site was the freedom to experiment. Grantland mixes the conversational with the dignified, the exquisitely researched with the incomprehensibly heartfelt. It’s unlocked something that nobody really thought could happen with sportswriters before.

Obviously there are great writers everywhere – Maisel, Thompson, Posnanski and others – but Grantland’s a place dedicated to writing and just writing. It’s blazed the trail for similar sites, like Sports on Earth and The Classical. And beyond its contributions to the industry, Grantland’s done a lot for me as a sports nut. It’s provided a home for a lot of brilliant people that otherwise would have been horribly misused at a more traditional news site, or worse, never given a chance at all. I loved Brian Phillips’ work at The Run of Play, and I’m glad that he’s getting paid real money to write now. Holly Anderson, too, at Every Day Should Be Saturday. Katie Baker at Deadspin. Andrew Sharp at SB Nation. Chris Brown. Matt Hinton. Jason Concepcion. Rany Jazayerli…and that’s just guys on the sports staff. How can I criticize a site that got Ken Dryden, of all people, back into the game?

No place has integrated talent from blogs as seamlessly as Grantland has done. That’s not damning it with faint praise: it takes a lot of vision and a lot of chutzpah to do that. The Internet was supposed to level the playing field, unlock people’s talents, and give the best writers national exposure. It’s certainly succeeded on the last point: Once upon a time, for a longform writer it was Sports Illustrated or bust, and that’s not the case today. But there’s also a lot of people who for one reason or another never break into the mainstream media and get their start on blogs. The MSM sometimes does have a bit of a bias against blogs, so if aspiring sportswriters try to start writing through blogs, they rarely end up getting national exposure. Aside from people at the aforementioned Classical and Sports on Earth, I can’t even think of a single major non-Grantland sportswriter that started out at a blog.

That’s the part of Simmons’ vision that people don’t talk about enough. It’s easy to pay him the standard lip service and say, Yeah, he made it okay to be cool when you write, to be colloquial and talk about doing stupid things and having a good time. Which he did, to be clear – but that’s not why he’s important. He’s not W.C. Heinz, and there will always be people who look down on him because of that, but he knows he’s not Heinz, and while he always tries to become a better writer, he doesn’t try to imitate Heinz either. The only thing great people imitate is each other’s success. And Simmons and Heinz share one critical honor: Heinz was the most influential sportswriter of his generation, and Simmons is the most influential of his. So far, Grantland’s the reason why we can speak of Simmons in such lofty terms.

Simmons made Grantland, built it from the ground up, pushed it where it otherwise would not have dared to go, supported it where it was about to fall. He might not write that much for Grantland anymore, but the site will definitely take a hit. I’m not scared, though, because with the right people it can still be like that. Simmons developed the infrastructure, and he proved that if you bring in great writers and give them media-quality access and resources, they can do something spectacular. But as ESPN’s leadership alluded to in their official statement, the factors I’ve identified are not dependent on Simmons anymore. Grantland has “a great team in place.” If ESPN can keep the talent flowing in, Grantland will be just fine.


ESPN decided that Simmons was expendable. It’s hard to think of Simmons as expendable, given that I’ve just spent a thousand words praising the guy, but ESPN’s a business. Sports are a business. Great sportswriters have a longer shelf life than great athletes, but people still cycle out of journalism; Grantland wouldn’t have so many new writers coming in if old writers weren’t already heading out. It’s a cold way to end things, to be sure, but it’s just the culmination of a long and frankly tiresome series of disputes between Bill Simmons and the Worldwide Leader. In any case, though Simmons clearly provides value, his contributions are difficult to quantify. He doesn’t write that much anymore, and his writing was his biggest draw. When we talk about Bill Simmons, we’re talking about the brand of Bill Simmons. And as Simmons himself pointed out about NBA teams – which typically lose money but somehow sell for staggering sums – brands are hard to value, let alone define.

“A 15-year run like Simmons at a dot-com is almost like David Letterman having a talk show for more than 30 years,” writes Will Leitch. He’s not wrong. An Internet trailblazer himself, Leitch has carved out a niche for himself at Sports on Earth, but his old website Deadspin is hardly the sort of McSweeneys-crossed-with-The Atlantic-crossed-with-TMZ (goodness, that’s a horrible way to put it) that Leitch had originally hoped it would be. Maybe it never could have stayed that way. Leitch was too edgy for the mainstream and too philosophical for the Internet of 2008. When asked to write a roast of his Deadspin successor AJ Daulerio, he responded – only partially tongue-in-cheek – “AJ ruined Deadspin, thank God.”

But Simmons wasn’t Leitch. He paved the way for something that was unquestionably mainstream but incorporated few if any of the mainstream’s typical faults. Maybe Grantland will never operate with the breathlessly dignified respectability of your archetypical longform scribe, a Wright Thompson or a Joe Posnanski or a Rick Reilly, but Grantland was never really about breathless dignity. You get the feeling that the people who work at Grantland are the sort of guys that don’t put much stock in traditional notions of dignity in the first place. There’s always been a vaguely populist tilt to the world Simmons helped create.

Partly because it was online and partly because Simmons fought for more autonomy from ESPN Corporate, Grantland has a lot more freedom to talk about the things that a media writer doesn’t have time to say. The autonomy part is intuitive. But the online aspect matters too, and Simmons was one of the first guys to really try to take advantage of what online media could do. People talk a lot about “optimizing for mobile” and “user-friendly design templates,” and certainly these things are important, but looking at the big picture, going online opens possibilities in the craft of sportswriting itself that Grantland was more than happy to exploit.

The thing is, a lot of mainstream media still hews to the old print paradigm: your space is limited and you need to sell newspapers, so you can only cover so many subjects in so many words. Just write a good lede and get the information out as quickly as possible. In other words, it’s reporting, and while we couldn’t have creative sportswriting without insightful reporting, we need people who can make sports come alive with their words. For all the freewheeling of ESPN TV’s SportsCenter, ESPN still acts like a traditional news outlet. It reports the news. That’s just what it does. Most deep writing is confined to longform online and special interest stories on television. Neither constitutes the core of what ESPN actually does.

Though part of ESPN, Grantland was designed to be something different, the Life to ESPN’s Time. Armed with that vision, Simmons allowed his writers free rein to talk about things that news editors would never even consider. He wasn’t scared of longform: Brian Phillips got 10,000 words to talk about sumo wrestling and Japanese politics. But Simmons also published pieces that were shorter, in the middle ground between a column and true longform – the sort of writing that online blogs had pioneered. One of the first great Grantland pieces – something that I read and immediately realized, wow, this is the site I’ve always been looking for – only got written because Simmons had the guts to let Jay Kang discuss baseball and the immigrant experience on a national platform. It was a gorgeous 4,000-word story that if not for the Internet either would have been reduced beyond all possible nuance or extended beyond enjoyable comprehension. More to the point, it probably would never have seen the light in the first place. Trust the second-generation immigrant here: That stuff never gets published, because that stuff never sells.

The beauty of Grantland was that it could feature pieces like these. The Internet, and Grantland in particular, allowed us to reimagine what sportswriting could be – that it didn’t have to be all things to all people. Kang’s essay on baseball embodied that shift, and just as impressively, right as the site was getting started. Reading through “Immigrant Misappropriations: The Importance of Ichiro,” you get the feeling that this was the essay Kang had been waiting his entire life to write. Certainly it was the essay I had been waiting my entire life to read. It is, to be sure, profoundly and magnificently inaccessible – Kang was by no means writing for a general audience, and the unfortunate truth is that few people outside of the Asian-American sphere have the frame of reference necessary to understand what Kang needed to say. In its inaccessibility it is hugely imperfect. It is by no means the final word on the subject. But even in 2015, deep insights about the Asian-American experience in the media and the public sphere of the very country we proudly call our own are so rare that most Asians greet every glimmer of cultural acknowledgement beyond the utterly superficial – of being recognized as something more than a student or a tourist attraction, in other words – with the joy normally associated with the light at the end of the tunnel. I disagree a lot with James Baldwin, but at least he exists. He got a national soapbox and a literary megaphone. Kang isn’t as famous as Baldwin, but while his story might have only resonated with a couple thousand people, it meant the world to them. This is what we mean when we talk about the democratization of cyberspace.

These values that Grantland demonstrates are things that ESPN can replicate after Simmons – but Simmons can bring with him three points from his time at ESPN that belong to him specifically, and which show his continued value to whatever he does next. First, he has a reputation for being a good boss to creative writers, and he’s willing to let people explore what they’re really interested in, even if their ideas aren’t widely marketable. He trusts that good writing is worth reading precisely because it is written well. Second, he has a track record of being creative himself. Third, he’s got the work ethic to turn that creativity into something real and meaningful. He knows, in short, that “nothing any good isn’t hard.” “The hardest working guy at ESPN is Bill Simmons,” Wright Thompson said. “You show me the people who you want to be like, and they’re all totally different except for the fact that all of them work their asses off.” Simmons is that kind of guy.

Simmons has succeeded because he’s found the right people. He will attract the right people wherever he goes. We shouldn’t be worried about Grantland; we also shouldn’t be worried about Simmons.


All the fuss and furor about the Simmons exit has been about ESPN, but we haven’t heard much about ESPN’s side of the story, and we likely never will, because that’s not how ESPN rolls. ESPN’s a business. ESPN avoids controversy like the plague. ESPN keeps things quiet. (The fact that the 800-page ESPN oral history Those Guys Have All The Fun even got published continues to amaze me.) And most importantly, ESPN knows its priorities: it suspended Simmons for insulting NFL Commissioner Roger Goodell. Previously, Simmons had confined his dissatisfaction with ESPN to occasional jibes in his columns or isolated remarks on radio shows. The Goodell suspension gave Simmons’ rage more bite.

Yet Simmons’ anger at Goodell and ESPN, however justified or unjustified, had a strong sense of biting-the-hand-that-feeds-you to it. ESPN is a great place for Simmons because it makes trainloads of money with its TV operations. Reporting doesn’t make money, writers in particular don’t make money, and Grantland probably runs at a loss. (For decades, the Washington Post’s business model was based on the paper losing millions every year and the Graham family TV stations making up the difference. That led to strange instances where the Post irritated the government and the government threatened to make life difficult for the TV stations instead.) The money that keeps Grantland viable is generated in part by ESPN’s strong relations with Goodell and other key sports figures. Guess what Simmons did.

That leads us to the Simmons exit. Certainly it wasn’t really about the money. When ESPN doesn’t fund something, it’s not because it can’t, it’s because it’s decided not to. Does anybody really believe that giving Bill Simmons an extra million dollars a year is going to tank ESPN’s bottom line? They’re paying over a billion dollars a year to have the rights to Monday Night Football. That’s 17 games a season. Simmons’ salary is a lot to most people, but to ESPN it’s petty change.

ESPN’s financial dominance has two main implications for Simmons. The first is that against the backdrop of so much institutional money and power, Simmons became expendable. As much as I hate to use clichés, creative personalities with massive ambition often do rub their employers the wrong way. And while Simmons has been brilliant, it’s not like ESPN needs to rely on any one person to succeed. Historically, they will do anything to avoid giving off that impression. As ESPN insiders recall in Those Guys Have All The Fun, the prevailing wisdom at ESPN headquarters in Bristol, Conn. is that “we don’t need another Chris Berman.” No person is bigger than the corporation. Not even Bill Simmons.

ESPN has plenty of brilliant writers and visionary thinkers who are company men, and it treats them well. When Simmons clashes with ESPN Corporate, it underlines that he’s not a company man. But that’s not a good or a bad thing, and it doesn’t mean that Simmons is a better or worse person for it. It just means ESPN’s a lot more willing to let him go. In the words of James Miller, the most well-connected reporter in Bristol, “One could say with minimal originality, but considerable accuracy, that Bill Simmons simply flew too close to the sun.” But you could make a strong argument that flying too close to the sun, endlessly pushing the boundaries of the accepted and the expected, was what made Bill Simmons great in the first place.

The second consequence of the Simmons fallout is that despite all the great things I’ve said about Bill Simmons, we’re still going to wonder whether he can succeed away from ESPN until he actually does succeed. ESPN picked up Simmons from AOL, and it’s easy to imagine a world in which Simmons never joins ESPN, AOL begins its slide, and Simmons rides it to obscurity. Of course, Simmons’ drive and ambition would have led him to find somewhere else, and I’m sure that he would have been at least moderately successful there. But what company outside of Bristol would have given Simmons the freedom to be Bill Simmons? What sort of place would have funded 30 for 30, the project that gave him mainstream legitimacy and turned him into something more than a glorified “blogger” (this was back when “blogger” was a four-letter word)? What sort of place would have given Grantland the green light? (Or, for that matter, taken on the expense of running Nate Silver’s FiveThirtyEight?) ESPN’s an innovative company and always has been. Simmons benefited a lot from the culture it created.

The rest, however, is conjecture. All we really know is that ESPN helped make Simmons, and Simmons repaid them handsomely. He’s been a major creative force for The Worldwide Leader for years now, and Grantland – a fountain of creative talent – is something that ESPN will appreciate for years. But it’s important to remember that all the articles written about Simmons’ exit have taken for granted – rightly – that ESPN will be fine without Bill Simmons. And you know what? There are no guarantees in life, but if there’s anybody that can stay relevant after ESPN, it’s going to be Bill Simmons.


By now, the postmortems have been written, the laments (and in some cases gloats) have been made, and the only thing left is the exit itself. The New York Times (yes, the man merits a NYT article) pointedly commented that Simmons hasn’t said anything about the entire affair. That’s very unlike Simmons, who over the decades has cultivated a reputation for being a thoughtful, cultured, and occasionally restrained loudmouth.

Why so silent? Maybe ESPN’s asked him to sign a non-disclosure agreement. Maybe Simmons is just relieved, now that his fifteen years of combat tango with Bristol are coming to an end. Maybe he’s just too busy figuring out what he’ll do next: I can definitely see Simmons trying to get the Grantland writers to jump ship with him, a la Franklin Foer at The New Republic. (If Simmons actually pulls a Foer, we’ll probably find out by next week.) But in the end, Simmons’ silence doesn’t matter that much. The uncertainty doesn’t matter much either.

Any piece on the Simmons departure – and trust me, there have been plenty – will ask where Simmons will go. But I don’t think that’s the question we should be asking. The fun is not in where Bill Simmons ends up. The fun is in watching him go to work, because you know he’s always going to try new things, push the envelope, and eventually hit a winner. Nobody needs to start up a “Save Our Simmons” webpage, because Simmons doesn’t need saving. We’ll find out what he thinks, and we’ll find out where he goes, and we know he’s going to do something great. We’re just along for the ride.

Contact Winston Shi at wshi94 ‘at’ for further tributes to Simmons, like 4,000 words on why Joakim Noah is the NBA’s Billy Zabka. Go Cobra Kai!

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Winston Shi was the Managing Editor of Opinions for Volume 245 (February-June 2014). He also served as an opinions and sports columnist, a senior staff writer, and a member of the Editorial Board. A native of Thousand Oaks, California (the one place on the planet with better weather than Stanford), he graduated from Stanford in June 2016 with bachelor's and master's degrees in history. He is currently attending law school, where he preaches the greatness of Stanford football to anybody who will listen, and other people who won't.