Requiem for Grantland, From Someone Who Barely Knew It

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“What’s Bill Simmons like?

A lot of people have asked me that question since 2011, and it’s understandable—if I knew somebody who worked with him, I’d ask the same thing. But I don’t have a great answer, and people are usually disappointed to learn that I’ve never met him in person or even talked to him on the phone. We’ve emailed a few times, but nothing extensive, and he wouldn’t know me from Adam if we met on the street.

I can say the same for almost everyone else at Grantland, where I worked full-time for two years, and freelanced as recently as this spring. In that time, I wrote more than one million words for the site, which I know because someone tracked it online. Still, the inner workings of the place were foreign to me. I worked from home in North Carolina, and only visited the Los Angeles offices once, in 2012. That trip produced nothing in the way of special insights—mostly, I was just surprised by how much it looked and felt like an ordinary work space, with open gray cubicles, industrial carpet, a few closed offices along the wall, and a larger corner office with a couch where Simmons worked on the days he came in. I wasn’t expecting bean bag chairs and ping pong tables, exactly, but I didn’t think it would so closely resemble the headquarters of a mid-level insurance firm.

As someone who had suffered in an office environment for four years, I recognized the familiar claustrophobic frisson as I stared at my computer and counted the minutes until 5 pm. I left for home feeling grateful that I didn’t have to enter that space every day, even though the people were far more interesting than those I’d encountered in previous gigs.

So even though I was writing for the site, and writing often, I mostly experienced Grantland and its writers the way everyone else did—from a distance. My intimacy with my co-workers started and stopped with Gmail. And the same is true about my relationship with Bill Simmons. I’ve read a handful of remembrances since Friday, when ESPN shut Grantland down following Simmons’ departure and the exodus of four editors, and they fall into two camps—those who regret some aspect of how they behaved and wished they had appreciated it more, and those who are full of praise for a place that already fills them with nostalgia.

I don’t have any regrets about my time at Grantland—I’m the sort of person who is always just a little bit out of the loop, but I also knew, at least in the abstract, that I had lucked out. I worked hard, and I don’t think I was too much of an asshole. But I can’t romanticize it, either. It quickly took on the rhythms of work for me, and since I’m incapable of appreciating good fortune for more than three seconds after it strikes, it never felt like a personal golden age. Maybe that will come later, when I’m destitute and broken and writing listicles for ten dollars a pop, but for now it already feels like a time and place that’s fading in memory.

What’s left, for me, is the acute strangeness of the fact that I had the job at all, and that Grantland ever existed in the first place. Like many of my fellow writers, I came from absolutely nowhere—a blip on the Internet radar, with no reputation, few noteworthy clips, zero connections, and the kind of talent recognized only by myself and my mother (and she had her doubts). By all indications, the world of online writing was going to steam onward without my participation, and if you had analyzed my situation in early 2011, you would have said, “man, you need to get really, really fucking lucky.”

I got really, really fucking lucky. It’s all because of Grantland, and it’s all because of Bill Simmons. I won’t pretend that my implausible discovery was of any great importance, but I think by telling my story, I can also illuminate one of the site’s noblest legacies—Simmons took a collection of outcasts, who had been ignored by traditional media and were flailing in frigid Internet waters, and he gave us a chance.


Shane Ryan in March 2011: On the rocky road. Attended Duke University despite wanting to be a writer, which is really not much different from attending Wharton because you love the theater. Graduated with a useless English degree, worked as a janitor in Saratoga Springs, made a bad documentary film for an environmentalist group in Asheville, NC, walked out of a PA job on the set of a terrible movie starring Tom Arnold and Tim Daly, got kicked out of one home, got too desperate in another, moved to Brooklyn, spent a 22nd birthday transcribing an interview with a Japanese makeup artist at a temp gig, landed a boring desk job at a cancer center, spent four years there while holding on to the writing dream, finally submitted two short stories to 40 different literary magazines, got a truck load of rejections (and one acceptance, six years later), decided to kill work-related boredom by writing a sports blog, applied to journalism school, moved to Chapel Hill, NC, got a fellowship at the school’s new digital news initiative with an editor who was fired within two months for sexting an undergrad, failed to attend useless meetings after that, was threatened with the loss of the fellowship.

So there I stood in March, 28 years old, wondering if they’d sack me—if nothing else, I thought, it would be an appropriate end to a pathetic career. In the meantime, I asked if they’d send me to the ACC basketball tournament. They gave me a grudging yes, but only wanted to publish a few short blogs. That sounded like a chance to watch Duke play from very good seats, for free, with very little work required. I agreed.

I drove to Greensboro with a friend, a fellow J-Schooler, on Thursday, Friday, and again on Saturday. When the semifinal games finished that last afternoon, my friend told me that a local radio host had invited him to dinner. I knew the host by association, and assumed I’d be invited to come along—after all, he was my ride. But maybe he thought a job was in the offing, or didn’t want me along for other reasons, so he told me with a shrug that I was out of luck. His indifference left me stranded late on a Saturday, an hour from home, forced to find my own way back.

This was not a death sentence, but for a number of reasons, it felt awful. I was almost 30 years old and going nowhere, and I had come to realize that whatever talent I thought I had meant nothing. Now this friend was going to rise like a meteor in the sports journalism world while I became an old bitter drunk ranting about what might have been. I felt betrayed, and hopeless, and very angry. Even the way he delivered the news, with a sort of satisfied solemnity, felt like the way you talk to someone who could never quite get his shit together. And if you wasted much time caring about his feelings, you might just get dragged down into the same morass…better, in all, to cut the anchor loose. “You’re a failure,” he might as well have said, “and I’m sorry, but not that sorry.”

I didn’t want to be that person—the kind for whom the rhythms of success would always be a mystery while my peers passed me by—but there I was. My face flushed, he left, and the tears that formed in my eyes when he was gone made me angrier still. I willed them not to fall, if only to maintain some control over a rotten situation.

Even when I managed to find a ride home, the anger didn’t go away (needless to say, the friendship ended that day). I came home and channeled the emotion into a blog post examining the strained, fruitless relationship between sports media and the athletes they covered, and discussing an unpleasant interaction I’d had on press row. I called it “The Truth About ‘Sports Writing.’”

I’m not sure how I feel about that post, which you can find here. It definitely reads like the rantings of a dilettante blogger playing the role of “journalism expert” for a day, and with more experience under my belt in 2015, parts of it make me cringe. On the other hand, I think I nailed some of the problematic dynamics, and almost five years later, I share many of the same complaints with my younger self.

The content, today, doesn’t matter to me—I’ve forgiven myself for everything I got wrong. What matters is the fallout. That post reached a wider audience, by far, than anything I’d ever written, and the reaction was enormous. Many readers, particularly those in the sports journalism establishment, were irate. Many cheered me on for sticking it to the man. More than a few veterans gleefully told me that I had just destroyed any chance of a career in journalism, and I believed them. For two days I walked around in a kind of panic, having no idea how to deal with this kind of attention. My fear that the doomsayers were right prompted me to write an apology, but deep down I knew I’d already sabotaged myself for good.

But it’s funny how life works, and how often the consensus is wrong. Far from burying me, that blog post sparked a career that had been languishing somewhere between dormant and dead. Chris Jones (Esquire, and later Grantland) wrote a post at his now-defunct blog taking me to task, but throwing me a few compliments along the way. Writers like John Feinstein and Tim Layden wrote helpful notes telling me what I’d gotten right, and where I’d gone too far. And in a moment that would change the direction of my life, Bill Simmons found the post and sent me an email.

He started by chastising me for capitulating so completely in the apology, which, with the benefit of hindsight, is painfully good advice. You went too far, he told me, but you’re young, and that’s all you needed to say—get used to taking hits for your writing. Second, he told me I was writing too much and that I would burn out (I haven’t taken this advice, but I can’t help it). He told me I had the chance to be a real writer, and to stop worrying about traffic and focus on quality. Last, he asked me about myself—age, life goals, etc. I think he expected me to be much younger than 28, and may have been slightly disappointed at the truth, but he never mentioned it.

That first email was all I got at the time, and when summer came I began interning (for no money) at the Charlotte Observer. I loved the reporting part of the job—it was a thrill, and I could see myself doing it for a living. But I hated the way my editor would summon me to her desk and change every sentence in an 400-word story, for no discernible reason, in a process that could last over an hour. She meant well, but it was agony, and I didn’t get the sense that she particularly loved writing in the first place. She works in PR now, and when I heard about that career change, it didn’t surprise me.

At night I stayed in a rented upstairs room in a house in the Charlotte suburbs, trying to read books about Durham’s history and plotting to write a book of my own about local high school football. One night, missing my girlfriend (now wife), I was watching the Dallas-Miami NBA finals on a tiny television and decided to write an essay about LeBron. When I finished, I realized I had no place to send it, and I got that same feeling from before—that I was writing without purpose, and that I had embarked on a career with no hope. I was just biding time until I returned to a job I hated, I told myself. To a lifetime of anxiety without fulfillment. It sounds melodramatic, but my capacity for envisioning a bleak future had no room for the romance of self-pity I’d practiced in childhood. Now it was all fear.

So what the hell, I thought. I’ll send the story to Simmons. It felt like an audacious move—I’m not sure why, but I thought maybe it could get me in trouble. I wondered if he’d tell me that he was busy, and to leave him alone.

That was June 3. Here’s what I wrote:

Mr. Simmons,

I know we haven’t been in touch for a while, but I wanted to touch base. I’ve started writing once weekly, like you suggested, and though it was hard I turned off the page view part of my brain.

Incredible game tonight.

Anyway, I wrote something about the Finals that I thought you might like. It’s just an essay I’ll either put on my blog or at this site called the Good Men Project Magazine whose editor approached me, and it’s an example of what I like to write when I’m not updating daily.

I’m kind of hoping to catch lightning in a bottle here, both for you to read this e-mail and have 15 minutes to read my piece, but if it works out, I do appreciate the time.

Hope you’re well,


The mention of the Good Men Project was designed to make me seem less like the desperate supplicant I was. Reading that email now, I can feel again the loneliness in it—the sense that it comes from a person talking into a void, and that the person knows it, but can’t quite relinquish hope.

I sent it off at 12:42 and went to brush my teeth. He wrote back 16 minutes later—I like it, he said, let me send it to my editors. I didn’t sleep well.

The next night, I got this email:

We have a request for you…

We have a spot open for someone who would write twice a day on our sports blog, between 450 and 800 words depending on how you’re feeling it. One of those pieces would be a daily morning recap (hopefully that feels unique) of what happened the night before (except for monday which would be a recap of the weekend). Come up with your own spin on it.

Would you be up for doing a test run for next week for 3 days? You’d send us 2 pieces per day… One would have to be in at 815am, the other would be 2:00pm. Let us know.

The obstacles rushed to the front of my brain in an odd, defensive reaction—I have to be at the paper all day, Monday through Friday! What will they say?! And almost immediately, the second thought—my God, who gives a shit? And then the elation—this was a legitimate shot, the thing I’d dreamed about, but that always seemed so far off.

The following Monday through Wednesday, I woke up early to write the morning recap, and ran back and forth from the office on long “lunch breaks” to write and publish the afternoon post. I created a separate blog so I could just send Simmons and the editors a link (it still exists here), and I threw caution to the wind. I refuse to go back and read it now in case it’s bad, but I know that I took risks and I tried to let my voice shine through with passion and humor and anything else I could muster. I’m sure it looked like madness. On Monday afternoon, one of the editors accidentally copied me on a reply-all:

Hey, I back up my original stance. The looong piece he sent us wasn’t so great. The blog, however, is good. And this, despite its weirdness, I really liked! (Where was the baseball though?) Mostly, i liked that he took a risk here to show off some of his writing chops. It paid off, even if it seemed out of place.

After day 1, here are my blogger power rankings:


The negative thoughts on the longer piece flew right over my head, because he had ranked me in first place. Over the next two days, they sent encouraging notes (“this is heading toward a really good place”), and I realized that this insane notion, working for Grantland, might actually happen.

The prospect was tantalizing. “So close I can almost taste it,” I wrote to my girlfriend that Tuesday, and my emotions flew to extremes. One minute I was convinced it was a sure thing, and the next I knew beyond doubt that it would slip from my grasp and torture me for the rest of my life. Seeing those exchanges again, the euphoria returns—no matter what happens in the rest of my career, I’ll never feel that original sheer elation of going from nothing to everything in a span of a few days. By the end of the endless week, I had the job.


On June 20, I wrote my first piece for the site, which was a version of what became About Last Night, a daily recap post I would write for over a year. Eventually I started writing longer pieces, and traveling for features, and feeling like a real journalist.

My time at Grantland wasn’t always perfect, but sometimes it was, and everything’s that happened since, from writing a book to landing here at Paste, was made possible by that strange series of events sparked by a friend leaving me behind in Greensboro.

What’s remarkable, having read the requiems of my fellow Grantland writers in the past few days, is how many of us share these unlikely origin stories. Bill Simmons and the editors he hired cared a lot about writing, and they cared about discovering new people. I wonder if, in some way, the fact that we were obscure gave us a sort of appeal—Simmons has a definite anti-establishment perspective, and he came from a nontraditional background to become the biggest sportswriter in America (the world?), surging past his traditional counterparts in the process. I suspect that, to some degree, he saw himself reflected in us.

I remember one friend, a longtime sportswriter who had worked at newspapers and regional Internet sites, looking at me askance when I gave him the news. “I’ve been doing this for 20 years, and you’re getting a shot?” he said. I understood—it felt bizarre to me, too, and it still does, and I’m sure it looks unfair from the outside. I think that if I had been a newspaper writer for five years instead of someone who had flitted around New York and North Carolina without much purpose, maybe I would have been overlooked.

Then again, I never would have written the kind of pieces that drew his attention in the first place. That’s what made Grantland so unique—Simmons looked everywhere, into the dimmest corners, to seek out the variety of voices that came to make up the site. He found people like me, who were writing only because they loved to write. Some of the people he found were bad or gimmicky writers, and maybe some people believed that about me. But some of them were brilliant, and I think that’s an overlooked truth about what he accomplished—if you’re legitimately going to seek out voices from the fringe, and try to create something edgier than the drab sportswriting that permeates the market, you have to accept a certain amount of failure.

The risk has to be real. I recently compared the situation at Grantland to American film in the 1970s, when producers and studios had no clue how to turn a huge profit, and could only throw money at talented directors in the hopes that they’d make the next Easy Rider. That pay-and-pray strategy lasted a decade, and unearthed directors like Robert Altman and Martin Scorcese and Terrence Malick. It also yielded a number of expensive bombs.

The difference is that Simmons wasn’t harvesting that kind of writer because he was clueless, but because he thought it would make Grantland exciting and unique and unpredictable. And he was right.

In the late ‘70s, Jaws happened, and Star Wars happened, and movie studios realized they didn’t have to rely on directors anymore. The blockbuster industry was born, and the greatest artistic era in American film ended. Grantland died in a similar fashion—it never made a ton of money, it was too smart to draw huge traffic numbers, and it ran up against a corporate bureaucracy that couldn’t handle the eccentricities of Simmons’ personality. They wanted him to fall in line, but he’s not the kind of person to fall in line, and so he left for a perfect destination—HBO.

In discussions about Grantland, it seems like a lot of people take joy in pointing out that its death won’t affect the company’s bottom line. Financially, it’s like water off a duck’s back. But if you subscribe to the radical notion that life is about more than profit margin, I would argue that losing Simmons and Grantland would be a tremendous setback for anyone.

Where, in the vast system, are the special things? The odd things? Where are the people who diverge from the bland company mindset? If we’re not striving to give those voices a space, then what story are we telling ourselves about the future? Where’s the soul?

Yes, Grantland lost the traffic wars to sites of lesser quality. Yes, it spent lots of money without turning a huge profit. And if that’s how you judge value, then you probably never appreciated Grantland in the first place, and you probably hoped it would fail. You can cheer loudly with the other smug realists the next time a place like CNN dumps a place like Sports Illustrated for a place like Bleacher Report, and root for the day when all writing is done by robots—if that’s who you want to be.


The world of Internet writing was already homogenous when I wrote my angry blog post in March 2011. It’s more so now—the weird people are ignored, or shunted back into the dim corners. When I landed the Grantland job, it felt like I’d been delivered from certain obscurity. To steal a phrase from Thom Yorke, I had jackknifed the juggernaut. It may be that I’ll soon slip back into the place that scared me so much, but at least I had a chance. The odds are longer now, and they’ll get longer year by year until we become a diverse array of faces who all think the same way. Grantland gave me a shot at beating those odds. Younger versions of myself now have one less shot, and that’s what we’ve lost.

So if you ask me what Bill Simmons is like, I can’t give you a compelling answer. I don’t know him. But I can tell you from a distance how he used every bit of influence to carve out an improbable space, and how he made us believe that the hurricane raging outside the window was just a passing cloud. And how we believed in the autonomous kingdom, and how we’ll never go back.