Ten years later, it’s clear Grantland can never be replicated

The branches that grew out of Grantland, the boutique digital sports and pop culture outlet founded by Bill Simmons at ESPN in 2011, touch nearly every inch of the sports media landscape today.

Both in the faces we see and the kind of content we consume, Grantland changed sports media greatly in its short run, which ended a decade ago this week. In four years, Grantland served as a proof of concept for Simmons’ core beliefs about the business: that digital sports talk was the future, that middle-brow sports content had the most staying power, and that great writers make the best stuff. The industry looks far different from it did when Grantland was the tasteful fan’s go-to, but many of the most popular analysts and the way they cover sports are entirely recognizable to anyone who read, watched, or listened to Grantland content in the early 2010s.

When it launched, Grantland became home to Simmons’ popular column and podcast as well as a network of other shows and editorial verticals crafted in his image. At ESPN’s Page 2, Simmons crusaded against stodgy newspaper dunces and blurred the lines between sports and the rest of his interests. Grantland proved that others could wear his hat, and that this type of work had broader appeal than just Simmons’ faithful readers.

Many of the sports column formats that Simmons popularized, from diaries to email exchanges to retrospectives to character deep-dives, became entrenched across the internet once Grantland started publishing them. By taking gimmicks like this seriously, Grantland’s roster of writers developed a readership of smart sports fans with a goofy streak.

And damn, what a roster. Zach Lowe, Bill Barnwell, Wesley Morris, Chris Ryan, Louisa Thomas, Rembert Browne, Jason Concepcion, Molly Lambert, Brian Phillips, Shea Serrano. Even with the caveat that it was working with an ESPN budget, the site assembled a group of brilliant young writers that will never be rivaled. These people continue to be the defining voices on their beats at publications that matter, a decade later. At Grantland, they could be irreverent, obsessive, experimental. They wrote like they knew they were the best thing going.

As a teenager, I ate it all up. We all say that about the things that defined our taste and passions in adolescence, but in the case of me and Grantland, I mean it literally. I would get badgered by high-school teachers for having my iPod Touch out, connected to the campus WiFi, reading everything from NBA blogs to athlete profiles to recaps of Mad Men episodes and thinkpieces on tabloid figures whom I even knew I did not care about. The point was that it was on Grantland.

What made Grantland unique in its time, however, was not its writing. By the time he got approved for this passion project, Simmons had a hunch that podcasting was the future. At Grantland, he greenlit shows like Do You Like Prince Movies, Girls in Hoodies, The Hollywood Prospectus Podcast, and what remains the best NFL podcast of all time, hosted by Barnwell and Robert Mays. Once I heard someone describe the goal for Grantland content (and later, The Ringer) as letting you in on the conversation happening between the smartest people at the bar. Podcasts allowed us to literally hear these people do their taste-making and ideation in real time.

The potential for podcasts as business and conversation drivers was even greater than Simmons may have realized. The Pod Father has said that investing in and monetizing these shows was one of the biggest sources of friction between he and ESPN management over the operation of Grantland (the digital audio and video space remains a glaring weakness at ESPN). At his next stop, podcasting would carry Simmons into a lucrative acquisition and financial windfall, changing the sports content industry once again.

The story of how Grantland came to an end is well-known now. Simmons continually clashed with management in Bristol until a fateful podcast episode in which he dared his bosses to punish him for calling the NFL commissioner a liar. They obliged him. Before long, the same bosses chose not to extend Simmons’ contract. After an exodus of his core creative team, he huddled with them to ideate on what would eventually become The Ringer. Back at Grantland, the short stint of ABC’s Chris Connelly was not enough to save the expensive, carved-out site. Staffers found out it had been shuttered from social media.

Within four years, The Ringer was acquired by Spotify. The podcasts became nearly the entire business. While some of the core principles behind Simmons’ creative vision continue to drive The Ringer’s podcast strategy and the coverage on each of its shows, the longer you listen, the more apparent the limits of conversation and chatter become. Articulate, thoughtful writing has the power to captivate people in a way that even the best podcasts cannot. In a podcast, ideas are confined to a question’s answer or a prompt’s response. A great column or feature flows straight from mind to page, charting new territory and imagining new ways of experiencing life.

Most of all, Grantland was a fantastic website run by great writers. The direction of the industry since its shutdown demands the contrast between writing and new formats, but then, great writing was a perfectly justifiable reason to have a company. Grantlanders also had exquisite taste. The sports staff’s embrace of analytics or the culture staff’s hype for Peak TV and auteur directors can seem hackneyed by our standards; these people stitched these played-out passions into the fabric of the internet.

Taste didn’t die with Grantland, but I fear it dies a little more in tandem with the minimization of great writing. Grantland taught me about the world. The places that a young sports fan might go to learn about it now have answers that, rather than leaping out of a thinking fan’s mind, is programmed for pre-roll video ads or subscription revenue.

With a bloated roster and constantly shifting directives, Grantland burned out fast. Its failure to survive even with that absurd advantage underscores that the website as a business model was dying. It rests in a graveyard next to the old Gawker, Deadspin, SB Nation, and many other great blogs that impacted readers like Grantland impacted me.

In its place, the sports internet that Simmons and Grantland helped reimagine pushes forward. The tenor and structure of the conversation is the same, appearing in new forms. Podcasts are an imperfect spawn of blogs, but they will do. Websites like Defector and smaller Substacks and Patreons allow smart sports minds to iterate on what Grantland and its cohort cooked up.

Grantland was a transient space where clever fans convened. A pit stop between versions of the internet, of sports fandom. The type of inflection point you only see looking backward. After Grantland, sports writing no longer paid the bills, and being a diehard was a requirement rather than an incompetence. After Grantland, sports content could be anything its creator wanted, and audiences were spoiled from a very good run.