In the ten years since Grantland – the boutique ESPN sports and pop culture website – folded, its legend has grown. And that legend wasn’t small to begin with.
Not many sites have received as much coverage in their entire lifespan as Grantland did before it even launched. Then-Deadspin editor A.J. Daulerio crashed his colleague Tommy Craggs’ meeting with John Walsh, a pre-hiring formality of sorts for Grantland, by sending someone in a pink gorilla costume. Nicholas Jackson wrote a confident proclamation in The Atlantic that the site was doomed before launch. Grantland founder Bill Simmons told the New York Times Magazine of the work required to make the site, “I’m not sure I would do it again.” He also, in a sign of the times, said that an ESPN employee by the name of Stephen A. Smith should be writing more and had “become too big of a yapper.”
Once the site launched, coverage accelerated further. Deadspin took regular potshots at the site and set up a series called “The Grantland Comments And Corrections Desk,” for which readers could send them typos or factual inaccuracies they found on the site (there were quite a few in those early days). Business Insider ran a best-and-worst after the first month of publication. Thoughtful reviews of the site appeared on major websites, minor websites, and random blogs.
“People were tracking who they were hiring, and who they weren’t hiring, and a lot of people had their feelings hurt about not getting hired,” Brian Phillips, a staff writer for Grantland, told me in 2023. The only similar sportswriting mania I can recall reading in recent years is this GQ piece on the buzzy launch of The Athletic.
Yet for all the reaction, the site’s creation was harried. Five editors — Simmons, Dan Fierman, Jay Caspian Kang, Robert Mays, and Lane Brown — had worked long, stressful days in a bare office in LA Live. They spent a while without a single copy editor. Wake-ups were as early as 4:30 am so that they could post articles on an East Coast schedule. Given the small staff and sheer length of many of those early articles, mistakes were inevitable. One day, ESPN forgot to renew the domain. (Naturally, Deadspin tried to buy it.)
Grantland lifted off with a number of lengthy, commemorative pieces that remain integral to the site’s identity. On the third day of publishing, Alex French and Howie Kahn produced a masterful oral history of the National Sports Daily, a well-funded and short-lived sports newspaper from the 1980s, helmed by the late, legendary scribe Frank Deford. The message was clear: Grantland intended itself to be the Daily’s successor. (At an event celebrating Grantland after it folded in 2015, staff writer Jordan Conn said the piece caught his eye for its “sheer fucking audacity.”)
Robert Mays followed up the National oral history with one on Friday Night Lights as it wrapped up its brilliant run; Eric Raskin put together the oral history of the enduringly controversial Ray Leonard-Marvin Hagler superfight, driving to the Boxing Hall of Fame at four in the morning to secure the vital and previously elusive Hagler interview. Kicker quotes packed punches and staying power. Early articles skewed long and personal, to occasional mockery. But everybody wanted to write for Grantland.
Sam Eifling reviewed the opening days of Grantland for the Columbia Journalism Review in June 2011 and wrote for the site himself in August. James Andrew Miller covered the eventual downfall of the site extensively, having written a piece for them in 2014. A former Grantland freelancer told me that oral histories paid out at $5000 (reader, my eyes bugged out of my head), longer features could be up to $1000, and short blogs ranged from $250 to $500 – but they found out after the site closed that other freelancers had been getting paid more, maybe by a lot.
With ESPN’s budget behind them, Grantland hired the best writers money could buy. “The pace of corporatization of online media was a little bit slower than the pace of popularization of online media, which meant that before there were established career paths in legacy institutions in online media, there were a bunch of writers that had large readerships and had gotten well-known online,” Phillips told me. “To me, the biggest thing Grantland had going for it was that it had this big pool of writers like that to draw from when it was staffing itself.”
When those writers got to Grantland, their voices honed by blogging, they were let loose to be their best selves. “Certainly up to the time, the best job I’d ever had,” Sean McIndoe, who covered hockey on staff for Grantland, told me in 2022. “It was a writer’s paradise. It was everything that, as a writer, you would want. You had freedom, you had budget, you had no pressure about how many views you had to get, there was no clickbait. The instructions from up above were basically, ‘go out and do good work that you’re proud of. Do as much of it as you can, but we’re not gonna tell you how much you have to write, or what kind of traffic you have to get. Do good work that you’re proud of, and the rest will sort itself out.’”
Louisa Thomas, a staff writer and later senior editor for the site, told me in another 2022 interview that “I went to Wimbledon. I got to see Usain Bolt run. I went to a Division Series for baseball. I went to the NBA playoffs. I had a bunch of amazing experiences. There was a real sense that there were not a lot of obstacles. If you wanted to go somewhere and you made a case for yourself, they were like, ‘go do it.’” Thomas also said she had the freedom to try on multiple voices as a writer, experimenting before settling into a more restrained style than many of her colleagues.
The site evolved naturally based on the writers’ preferences. “I think Bill at one point said he tried to hire people who were a good hang,” Thomas said. According to one writer, Zach Lowe shouted out Kirk Goldsberry’s heat maps in a meeting; soon after, Goldsberry worked at Grantland. Roles shuffled around, with editors becoming writers and writers becoming editors. Surrounded by best-in-field scribes, Grantland writers were motivated to do their best work just to keep up.
“It was a good site!” McIndoe said. “If I hadn’t been working there, I would have been reading it all the time, and even working there, I was. I’m a hockey fan, I’m a football fan, little bit of baseball. Not really an NBA guy, but I’d still read the NBA stuff! I’d read Zach Lowe, because I’m sitting there going, ‘this is just really smart, good stuff.’ It was a really fantastic site.”
Raskin concurred from the freelance side. “I would assume that most of the writers on the site put a higher priority on doing their best work for Grantland. I know I did, especially in the early days. I pride myself on always handing in something that I’m proud of, but there was something more prestigious about writing for Grantland, and I think we sensed it, and I think you probably would take that little bit of extra time to make sure that you’d written that perfect lede to draw someone in and the perfect final sentence that’s gonna bring it all home.”
Phillips, who in my estimation wrote the best piece on the site, took it a step further: “There were times at Grantland when I was disappointed to be assigned a topic, because I wanted to know what another Grantland writer would make of it. I knew that if I were writing about it, they wouldn’t be. As a reader myself, I felt like I was harming my consumer experience of the site by writing for it professionally.” He laughed. “Yeah, it was a good place.”
Lengthy, access-driven pieces supplemented the quick, sharp blogs that covered sports and culture on the daily. Staff writer Amos Barshad spent a while trying to track down all the members of the Wu-Tang Clan ahead of their reunion album, resulting in another all-time great Grantland piece. The group’s publicist brought Barshad into their trailer before a show in Bonnaroo, where Barshad recorded details that later became a lede, including delightful anecdotes like “In the background, GZA sends U-God’s lollipop flying into the bushes.” Years later, he was scheduled to have RZA on a podcast. On his way to the studio, he received word that the interview was no more: he’d been identified as that reporter.
To help writers do their best work, editors worked daunting hours. On the Longform podcast in 2013, Jay Caspian Kang described 16-to-20-hour days as they constructed the site before launch. Thomas described her hectic schedule to me, even once the staff was better built out: “I had East Coast writers, and we were putting pieces up at 6 am. So let’s say I start work at 5:30 am. You work from home until 10, then I would get in the car and drive into the office. You would be there until 4 or so. I would go home, maybe I would stop at the gym if I had time, eat dinner, and work. One of my writers was on the West Coast, so she would file at the end of her day, at 6, for a piece the next day. I’d be working on edits with her, and I would sometimes work until 11 or 12. That’s a 19-hour day. There weren’t a lot of those, but there were, for sure, some of them.”
The Grantland site was – is, if you go back and read the archives, which you should – clean and relatively spared of ads. Subway, one of its main sponsors, seems a positively angelic company to get your money from, next to the gambling companies with their fingerprints plastered over most sports media outlets these days. If any conflicts of interest existed for the writers, they were few and far between.
“We had been in this really privileged position within the company, where ESPN had these multibillion-dollar deals with sports leagues,” Phillips said. “If you were a talking head on an ESPN show or a writer on the website, I think, to an extent, you had to tread carefully around what you said about those sports leagues. But at Grantland, we could talk shit about the NFL all day long, and did, and there was never any blowback from it because Bill just kind of blocked all of that stuff.”
At the same time, working under the ESPN umbrella with Simmons at the helm afforded Grantland great latitude in its budget and editorial strategy. Some pieces took several months to finish and came accompanied by original, intricate art. Writers traveled to Japan, Russia, and the Philippines. Satire featured. The NFL and NBA were the leagues covered most consistently, but Grantland also respected tennis, boxing, and other less mainstream sports.
Sometimes a story about a sporting event wouldn’t really describe anything that happened on the field. Short, reactive blogs remained smart. Delightfully weird, long features were a staple. Here’s the lede to Jason Fagone’s masterfully written “Dropped,” one of the best stories in 2014:
“I feel like I should let you know what you’re in for. This is a long story about a juggler. It gets into some areas that matter in all sports, such as performance and audience and ambition, but there’s absolutely a lot of juggling in the next 6,700 words. I assume you may bail at this point, which is fine; I almost bailed a few times in the writing.” I didn’t care for juggling and still don’t, but several passages from the story still ring through my head occasionally.
That same year, the site made its worst and most consequential mistake, publishing a story by freelancer Caleb Hannan in which he’d outed a transgender woman, Essay Anne Vanderbilt, thought to be selling a fraudulent golf club, to one of her investors. Vanderbilt died by suicide before the story went to publication, but Grantland still ran the piece. The story sparked a significant backlash and a conversation in various publications and corners of the Internet about the piece’s numerous mistakes, the drawbacks of longform writing, and transphobia.
Following a podcast appearance in which Simmons criticized NFL commissioner Roger Goodell’s, erm, manhood, ESPN suspended their star for three weeks. Then, in 2015, they elected not to renew his contract. Chris Connelly replaced Simmons after Grantland editor Sean Fennessey turned down the job; those I spoke with recognized that Connelly was put in an unworkable position as Simmons’ replacement, but unanimously disapproved of his performance in that role.
“He had a view of how the site should work that he brought into it that didn’t jibe with what the writers and editors wanted,” Thomas said. “That was tough. That was a lot of tough, because it definitely felt like a bit of a tone-deaf move, ESPN imposing their view on things.” Thomas, burned out from a year of her editing job’s attritional pace, took the moment to step back into her old writing role.
Phillips told me about a meeting he had with Connelly and Grantland features editor Rafe Bartholomew to discuss a planned piece for which he’d travel to Serbia to track down Darko Miličić, and Connelly asked several specific questions Phillips felt he’d be unable to answer until he wrote the piece. Previously, Phillips had enjoyed total freedom in where he went and what he wrote about – Simmons once called him up and asked him to provide a list of his top five destination pieces, in the hopes they could make them all happen.
Phillips told me he was sure the questions were all reasonable from Connelly’s perspective, but “to me, it was a very extreme breach of what I thought was the social compact at Grantland. The piece never ended up happening, because he wouldn’t approve it under the circumstances… I think at that point I knew, things are different and we’re in some trouble.”
The site weathered another blow when, the week of October 18, 2015, Fierman, Fennessey, Mallory Rubin, Chris Ryan, and Juliet Litman all left Grantland. (Fierman left for an editorial director role at MTV News; the others left to help Simmons build The Ringer, then an unnamed project. Both publications went on to hire several former Grantlanders, but MTV News shuttered in 2017.)
Deadspin reported at the time that Simmons had told his future collaborators their employment was conditional on not notifying anyone of their coordinated departure, so as to blindside ESPN; in doing so, they also left Grantland, which didn’t quite have enough editors to keep pace with its many writers at the best of times, with a severely understaffed editing team on short notice.
On the Longform podcast in 2017, Bartholomew (who politely declined interview requests) recalled maintaining the site in those final weeks. “The pace was out of control,” he told host Max Linsky of trying to support a large writing staff with so few editors. He described the period as “really difficult and painful, because we knew [the end] was coming,” and said it included “a lot of bad gallows humor.”
Thomas said, “Rafe Bartholomew, his heroics keeping that site going in the very end, he deserves a lot of credit there.”
Connelly announced the shuttering of Grantland on a conference call. Former staff writer Bryan Curtis has told the story of how he found out in the maternity ward as his wife was giving birth to their child. Steven Hyden, also a staff writer at the time, recently wrote on his newsletter Evil Speakers that he saw the news on Twitter minutes before the call. McIndoe, who was working remotely, told me that “The day the site shut down and they sent the email out to everybody saying, ‘Mandatory meeting at 12:00,’ I wasn’t on that list. They forgot to put me on that list.” He was watching a movie at home and received a message from fellow staff and hockey writer Katie Baker asking if he’d seen the message. “I’m like, ‘no, what email do you mean?’ She’s like, ‘I think you need to see it,’ and she sent it to me.”
Barshad recalls a dark day for the site, either when it closed or one “portending doom,” on which he went out for a drink, only to be met with more disappointment. “It was like a Miller High Life in a seven-ounce bottle, which I’ve never seen before or since,” he said.
The site’s ending caused a deep mourning and appreciation among its readers. McIndoe said the outpouring “probably saved my career in the sense that as one of the smaller names on the site, I could have very easily faded back into doing hit-and-miss freelance work, and that could’ve been it.” Instead, he found himself receiving messages from sites that “very frankly, weren’t huge fans of mine, but they were such huge fans of Grantland that they said, ‘okay, you’re the hockey guy from Grantland? We want you, because we want to be able to say we’ve got a Grantland guy.’ The site’s reputation was so high that people wanted to be associated with it even when it was done.”
“I had this pretty peaceful existence,” Barshad recalled of his time at Grantland. “I bet it’s similar to a lot of writers, that wherever they lived, they got to do their thing. I think we did talk about this somewhat. We knew we were getting a lot of freedom and support. Maybe I’m remembering it fondly because it was in the past, and now it’s over. I feel like it was this really unique situation that I knew wouldn’t be replicated.”
“[Grantland] changed my life,” Thomas said, who has written for the New Yorker since 2016. “There’s no question. Obviously, it changed my life. I wouldn’t be doing what I’m doing right now without it.”
There’s a curious balance in how Grantland is remembered now, another decade on: nearly everybody who read it remembers the site fondly, but also agrees that media trends make it virtually impossible to replace.
“I can’t say I think that the Internet was never the same after Grantland, because I think what Grantland was doing just basically got wiped out by the tsunami of other trends and right now stands as an unfulfilled potential,” Phillips told me.
May someone come to fulfill it before another decade passes.
