Grantland enthralled us by taking on the professional world with a university mindset

How will I begin the latest think piece in the wake of Grantland’s demise, you ask? Ironically enough, with an anecdote about Sports Illustrated.

There was a lot to digest in the memorable SI essay where LeBron James announced that he would be returning to the Cleveland Cavaliers in free agency, but there was one passage that stuck with me the most: “Miami, for me, has been almost like college for other kids. These past four years helped raise me into who I am. I became a better player and a better man. I learned from a franchise that had been where I wanted to go. I will always think of Miami as my second home. Without the experiences I had there, I wouldn’t be able to do what I’m doing today.”

We’ll never know if that came straight from LeBron’s head or if it was suggested by his talented scribe Lee Jenkins, but regardless, what a fantastic analogy. Beyond the cool concept of his Miami Heat tenure being equivalent to the average amount of time it takes someone to complete an undergraduate degree, it put a sentimental spin on the whole decision that would make Don Draper proud, presenting things as if his initial abandonment was never an abandonment at all—just a routine stepping stone that would allow him to spread his wings and mature before making his predetermined homecoming and moving into his family’s basement (excuse me, almost forgot the fresh graduate thing was just a parallel).

So a couple weeks ago, as I sat around in my new living space—also known as my family’s basement—and heard the gloomy news about Grantland being shut down after approximately four years, that number led me back to LeBron’s potent postsecondary analogy. And after mulling that numerical connection over for a bit, it also hit me that Grantland’s 2011-2015 life span matched up pretty much perfectly with that of my undergraduate degree. Having pretty much worshipped the website for the last few years, that coincidence carried a lot of weight for me.

The more I thought about it though, the more I realized how scarily similar the lives of Grantland and my degree—most Arts degrees, really—actually were. Some of the ideas in the LeBron passage loosely applied to Grantland’s employees as well, but having two writing-based endeavours as the subjects of inquiry made for a much deeper and more telling comparison. There have been lots of attempts made recently to try and articulate the meaning/legacy of Grantland, but when it comes down to it, I think that the biggest takeaway from Grantland’s existence is that it was a professional website that lived like it was in university.



For many Arts students, the first year of university is a bit of a wildcard. Some of them might be set on a certain academic path, content to commit to it right away. But for others, the undeclared tag is a blessing, a free pass to take flyers on intriguing subjects like Gender Studies or Linguistics that weren’t available in high school. As Grantland’s creator and primary editor-in-chief Bill Simmons explains in the site’s inaugural article (ca. June 2011), Grantland opted for that kind of an adventurous approach when it was just starting out:

I would love to tell you that this website will work, that we’ll entertain you five days a week and blend sports and pop culture successfully. The truth is, I don’t know for sure. This site will keep changing over the next few month’s just like Jimmy [Kimmel]’s show kept changing in 2003, hopefully for the right reasons and not the wrong ones. We are still hiring people. We are still finding writers. We will eventually have a sports blog and a pop culture blog (launching next month), user comments (later this summer), a podcast network (ditto), a quarterly publication we’re doing with McSweeney’s (four a year, starting this winter), and who knows what else. You figure out what works, you figure out what doesn’t work, you keep moving. That’s the next nine months for us. Eventually, we will evolve into what we are. Whatever the hell that is.

Despite the self-professed uncertainty, Grantland was certainly on the right track when it launched. The vague blogs Simmons alluded to ended up materializing as The Triangle and The Hollywood Prospectus, which, throughout Grantland’s run, published insightful content while still managing to keep the site up to date with the fast-paced sports/pop culture worlds. The podcast network also evolved into one of Grantland’s biggest draws, allowing many of its diverse personalities to discuss an equally diverse array of subjects—what other website would give you regular podcasts about professional wrestling, food news, and the off-court lives of NBA stars? The quarterly publication and user commenting experiments didn’t fare quite as well, but, just like my short-lived Political Science minor and its ultimately negligible effect on my degree, they were nothing more than inconsequential footnotes to Grantland’s central story.

These logistical features were important in terms of the way Grantland operated, but nothing shaped the site’s eventual identity more than its contributors and editors. And in the beginning, they too represented somewhat of a wildcard. That wasn’t because Grantland would be heavily relying on unproven individuals in its infancy—if anything, it was the complete opposite.

Prior to the site’s launch, one of the few things the public knew for sure about it was that Simmons had recruited the likes of Malcolm Gladwell, Chuck Klosterman, Dave Eggers, Katie Baker, Jay Caspian Kang, and a few more of the most highly regarded 21st century writers to join the team he was still in the process of putting together. But as failed experiments like the 2012-2013 Los Angeles Lakers or Mick Jagger-fronted supergroup SuperHeavy have taught us, starry names don’t always produce the best results. Here’s how The Atlantic’s Nicholas Jackson sized up Grantland’s prospects just days before it went live:

Yes, Grantland’s “murderer’s row of talent” is (“HOLY SH*T”) impressive, but that’s just another reason why it’s going to fail. These people are way too expensive for what Simmons is trying to do.

If the site does succeed it won’t be because of the talent he’s brought in—it will be despite it. Simmons—well, ESPN—is essentially overpaying, because of their experience, old guys to act like new guys. Established sportswriters that will have to pretend they don’t have that experience ESPN is paying them for. These are smart, literary writers. Simmons is anything but—and he woundn’t disagree.

As it turns out, that was a pretty solid assessment. Although those established names were responsible for a fair amount of content in Grantland’s early days, their contributions quickly waned as the site really came into its own (Baker thankfully stuck around for the long haul, and Klosterman occasionally returned to the fray with an article or an appearance on Simmons’ podcast). Think of them as the crew of high school friends that went to the same university as you; you clung to them throughout the uncertainty of Frosh Week and September, but soon enough, they were either replaced or complemented by a host of new friends.

While the major players grabbed all the headlines in the lead up to Grantland’s launch, Simmons hinted in that first article that it wouldn’t be all about them for very long: “We had four goals for this site [….] the fourth was to hire the right blend of people—mostly young, mostly up-and-comers, all good people with good ideas who aren’t afraid to share them.”

What resulted from that was something truly wonderful. Not only did Simmons make good on his intention to develop promising young writers, he created an online haven that outsiders admired not only for its great work, but because it gave every indication of being—and was—the most supportive and fun writing environment that a sports/pop culture critic could’ve asked for.

There was some initial concern that Simmons would push his writers to try and replicate his own distinctive voice, but that was hardly the case. Instead, he gave them the green light to form their own voices and write with the kind of freedom that virtually no other major publication offered. Make no mistake, the site had rigorous standards. But they were the kind of standards that ignored the perceived range of angles that were ‘acceptable’ for a legitimate media outlet to explore. Grantland had lots of detailed analytic pieces that shed light on things like Rajon Rondo’s shooting patterns or the long-term industry impact of Radiohead’s Kid A, but it was also just as happy to publish a lengthy article titled “Going Way Too Deep Down the Rabbit Hole With Nicki Minaj’s Recent Bar Mitzvah Appearance.”

Operating out of this unconventional framework, Grantland’s personality completely embodied the mindset of the prototypical Arts student. It was sophisticated but embraced informality whenever it could. Its commentary was on point but sometimes came with hints of arrogance. It took pleasure in rebelling against the mainstream but only presented a flawed alternative (we’ll get to that soon).

But nothing gave Grantland more of a university vibe than the experiences its employees had while working there. To a certain degree that was directly tied to the actual work being done for the site. As Simmons has discussed since being ousted from Grantland, they were understaffed and overworked, trading in REM cycles to ensure that it was able to put out high quality, well-edited content every weekday. Few places inspire all-nighters more than university campuses, and what Grantland’s sleepless nights really had in common with the university all-nighter was the shared struggle.

When university students are up late cramming or churning out an essay, there’s a high likelihood that they’re surrounded by at least a handful of other students in a library or coffee shop. Part of the reward of finishing work for the night is triumphantly walking out of one’s chosen study space with a friend and unwinding together, maybe coming back to chill with whichever roommate is still awake, or even just running into someone you know and having a nice conversation on the way home. It’s a difficult grind, but everyone’s in the same boat, so you might as well make the most of it and appreciate the social experience that studying can foster.

I doubt there’s ever been a publication that had more comaraderie oozing from its proverbial walls than Grantland did. Literally every person who’s ever worked there has given glowing reviews about the staff atmosphere. Like university, it was a place you could arrive at with the reasonable expectation that you would be spending the best four years of your life there—except with Grantland there was a higher likelihood of things actually turning out that way.

A lot of that probably had to do with the fact that everyone at Grantland was doing what they loved for a living and had the added benefit of avoiding the typical constrictions that governed other publications. It certainly didn’t hurt that they all basically worshipped Simmons, who also may have instilled a bit of a ‘nobody believes in us’ mentality in the Grantland team that accelerated the rate at which they all banded together. I could keep hypothesizing, but Grantland staff writer Jonah Keri absolutely nails the explanation in this series of tweets that were published shortly after news broke of the site’s demise, so I’d rather you get it straight from the horse’s mouth.

I know not everyone likes to click on links in the middle of reading an article, but if you want to fully appreciate this article, Keri’s Twitter essay is required reading.

All done? Great, let’s keep going!

Keri’s affectionate words are just one of the many outpourings of appreciation that were publicly shared by the Grantland staff during that Halloween weekend when everyone was freshly processing the site’s closure. It’s beautiful to take in how much these people genuinely loved each other. Fondness for coworkers is something that inevitably develops when you work with them for a long enough period of time—and they don’t suck—but as something like Keri’s Shea Serrano tweet attests to, it was the effect of Grantland as a whole that enabled that to happen so staggeringly, even in the absence of real-life exposure to each other.

There unfortunately isn’t a “No assholes” policy in university and you don’t necessarily care deeply for people in a university that you’ve never met before, but the Grantland staff relationships were very much presented to the public as being similar to what you would expect from a group of university buddies: fun and, in spite of the whole higher education thing, pretty juvenile. The informality in their articles/podcasts was amplified in their Twitter feeds and they frequently let followers in on whatever inside jokes they had—rather than taking an all-business approach to the platform as many media figures do.

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Being fully immersed Grantland—daily visits to the site, keeping up to date on writers’ Twitter musings—was a pretty unique internet experience. You not only got to regularly read high quality commentary that already distinguished itself stylistically from most other outlets, you felt as if it were your friends that were producing it. To some extent that’s true of anyone who closely follows the work of any writer, but Grantland’s tone and social media presence upped the ante in terms of how much its writers were willing to reveal their personalities and let you into their worlds.

The problem was that not enough people cared to partake in the Grantland experience.

By all accounts, Grantland was an objectively great website. It vastly exceeded the initial expectations people had for it and received heaps of critical acclaim, but the site never found a way to leverage that appeal into web traffic. Grantland catered primarily to a miniscule demographic: the highbrow sports and pop culture fan who was put off by the glut of quick, simple writing that had come to dominate the internet. Its strategy was essentially to swim against the mainstream current and try to get the masses to buy into longform writing and offbeat coverage, but that never really happened. While it had the occasional article that blew up, Grantland remained for the most part a low-traffic niche website. Meanwhile, places like Bleacher Report and Buzzfeed—who covered similar topics—grew massively.

Recently on his new podcast with HBO, Simmons took some responsibility for not addressing the traffic problem sooner:

We should have made a lot more money than we did, and part of this is my fault. I always felt like we should just worry about the words—people are going to come—worry about the quality. The staff can back me up; I never looked at the page views and stuff, I never cared about that. I always was worried about the overall calibration and quality of the site, and I felt like in the long run we were going to win.

Attracting traffic isn’t the only way of generating revenue on the internet, but Grantland never took advantage of any alternative methods either. It didn’t monetize any of its content (unless you count the quarterly publications, which were scrapped after a couple of years) and opted for very little advertising on its interface. Simmons and the rest of the Grantland brain trust were optimistic idealists. It’s one thing to shun the low quality writing that has proven to produce page views, but it’s another to shrug off the real world consequences of running an unsuccessful business. Pardon the cheesiness, but, since it wasn’t paying the bills and dealing with those deficits directly, Grantland basically managed to have its cake and eat it too.

Until of course, it didn’t. Four years of employee salaries and operation costs was all that Grantland managed to squeeze out of ESPN before the sports conglomerate had seen enough to go ahead and pull the plug on the website it had reluctantly commissioned. Grantland was like all the students who get a free ride from their parents throughout undergrad, but get cut off for grad school or whatever else comes next. When you’re living off of someone else’s funds, you can afford to be idealistic and pursue creative greatness without worrying about its price tag. But if that benefactor’s benevolence runs dry, then you better find a new, more self-sustaining gig (or just another benefactor).

Grantland found that out the hard way, and so do most Arts students. English, History, Philosophy, and other writing-based majors rarely lead to a decent job for graduates that relates in any way to the branch of knowledge they represent. Students in those programs learn critical thinking, sure, but for the most part, they’d probably be able to function just fine in the workplace with no more than the skills they had coming out of high school.

Like Grantland’s writing, the essays produced by an Arts student are of little interest/value to the average person. My English professor was thrilled to read my comprehensive term paper on the recurring motif of scars in Michael Ondaatje’s work, but very few others would be interested in taking the time to sit down and read it—or commission me to produce more papers like it. Maybe a Buzzfeed-style ranking of the 12 sexiest moments in The English Patient would put my Ondaatje knowledge to more profitable use.

Sports and pop culture are two of the most accessible topics out there, but Grantland still couldn’t manage to build a big enough audience for ESPN to justify extending the website’s license to print its refined articles. Those who were loyal to the site will miss it dearly, but the bookkeepers at ESPN certainly won’t.

Maybe in the future somebody will build something resembling Grantland and figure out how to properly reap the rewards it deserved. Even if that never happens though, at least we’ll have gotten four outstanding years of a project that never should’ve been allowed to exist from a business perspective, yet did anyways. Grantland lived frivolously, but it also lived meaningfully—which is more than a whole bunch of other page view-obsessed publications can say.

So here’s to Grantland University; to the passion, the risks, the sleepless nights, the extraordinary friendships, the consistently great content, and the joy it brought devoted readers like me. I’m expecting many more big things to come from the Class of 2015.


One thought on “Grantland enthralled us by taking on the professional world with a university mindset

  1. Great stuff!

    My name is Derek and I’m the founder of the Fox Sports Engage syndicated sports and entertainment site In short, the site is a hub for the most talented writers from across the country and I think you would be a great fit. If you’re interested, feel free to shoot me an email at derek (at) nocoastbias (dot) com or derek (dot) hernandez (at) hudl (dot) com. Thanks!


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