Last Friday, ESPN announced that it was shutting down Grantland, its critically acclaimed sports and culture website. The move was not entirely unexpected, given that ESPN decided not to renew Bill Simmons’ contract in May.

Simmons was Grantland’s founding editor and its biggest source of traffic — without him the site would never have existed. ESPN is also going through broader cutbacks — besides Simmons, the company parted ways with television personalities Colin Cowherd and Keith Olbermann in recent months — and Grantland was a natural place to save some money.

Despite its critical popularity, the site never generated enough pageviews to justify the cost of its prestigious staff. As predictable as the shutdown was, it still generated a huge backlash. In a representative example for the New Republic Alex Shepard and Mark Krotov wrote that “Grantland, after all, was something special — it was nothing short of an alternate path for the internet, where pageviews were less important than rigorous passion.”

Grantland’s rise and fall since its founding in 2011 says something ominous about the viability of quality online journalism. The reality is that there are a lot of good young writers who can opine thoughtfully on any number of topics and a relatively limited market for their services. The only way they can be paid what they think they deserve is if someone, like Bill Simmons, comes along with a project, like Grantland, that is willing to lose money in order to publish high-quality writing.

But the story of Grantland is also a personal drama, about a formerly cool sportswriter having a mid-life crisis, and the cool young writers he hired.

Interestingly, Grantland was not always so beloved by people who write about media on the Internet.

Before the site’s launch, and in its first year, Deadspin published several articles that ranged from skeptical to derisive, including, “The 11 Worst Grantland Long Reads of 2011.” Essentially, the media critics were skeptical of Grantland because they thought it would be too much like Bill Simmons, who they found obnoxious.

But then something funny started happening: Simmons started hiring writers for Grantland who were very similar to the people who were criticizing him, and in some cases, hiring the very people who attacked him ruthlessly. Charlie Pierce, whose takedown of Simmons included the memorable line, “You are not the cosmos, son. Get ... over yourself,” found himself writing for Grantland.

Of course, this put Simmons’ detractors in a difficult position: If they wanted to maintain any intellectual consistency, they were forced to praise his judgment as an editor, regardless of how obnoxious they found him to be as a writer. And they did praise his judgment, but took advantage where they could, making sure to double down on their criticism of his writing.

On Deadspin, Tommy Craggs doled out the most backhanded of all backhanded compliments: “It turns out that Simmons has better, more catholic tastes than his own writing would suggest, which is the best thing you could ever say about an editor-in-chief and which is a really good thing in this instance, because a site built solely around that chuckling, incurious, cleverest-guy-standing-around-the-Phi-Delt-keg writing voice of his … would suck.”

Even today, media critics love to claim that Simmons was never good enough for his own site. As Shepard and Krotov put it, “none of the site’s most memorable pieces were written by Simmons … Grantland succeeded by being decidedly un-Sports Guy-y.” So what gives?

Why was Simmons hiring people who were ostensibly opposed to everything he stood for? Tommy Craggs thinks it was because Simmons “has better, more catholic tastes than his own writing would suggest.” I’d like to advance a more simplified explanation: Simmons had become part of the establishment, and all he wanted was to be cool again.

In 2001, Bill Simmons was cool, up-and-coming and subversive. He wrote a column on AOL that, as Bryan Curtis wrote four years later for Slate.com, was “a subversion of the traditional sports column, not unlike the way in which The Daily Show With Jon Stewart subverts the traditional nightly news broadcast.” (Curtis later went on to write for Grantland) He occasionally guest-wrote for ESPN, but his audience remained relatively small: totalling about 10,000 readers a month on AOL. And even his ESPN columns were provocative, featuring titles like “Is Clemens the Antichrist?”

In short, Simmons was revolutionary because he wrote from a fan’s perspective, and because he challenged sports writing conventions about length, propriety and impartiality. His articles often took aim at sports media personalities who he found pompous or ridiculous.

Now, fast-forward 10 years to 2011. Bill Simmons had just about everything. He was easily the most read sportswriter in the country, and his sprawling history of the NBA, “The Book of Basketball,” had debuted at the top of the New York Times bestseller list. His podcast, “The B.S. Report,” was downloaded over 20 million times a year.

But was he cool? Not even close. The cool people had gotten used to his writing-as-a-fan gimmick, and they were either sick of it or doing it better than him.

People were writing scathing takedowns of him in the same way he used to takedown newspaper columnists and play-by-play announcers. And his angry, anti-sports-media-establishment style had solidified into a mellower shtick — still entertaining, but no longer subversive.

In his “Welcome to Grantland” column written for the site’s launch in 2011, Simmons goes on and on about the camaraderie he already feels with his employees, who he describes as “mostly young, mostly up-and-comers.”

He writes about the bars they went to and the jokes they made while they were preparing for the launch, and he waxes nostalgic about his time in the early 2000s as a writer for the Jimmy Kimmel show.

It’s clear that Simmons’ favorite part of the whole Grantland venture was the chance to feel like a part of a group of young writers with big ideas.

Ironically, Grantland succeeded in being cool, but not in the way that early 2000s Bill Simmons was cool. The anti-establishment fire that made early 2000s Simmons cool had no place at Grantland. Grantland was cool in a polished, careerist way; its writers and editors always kept one eye on the way their work was going to be received. You might find quirky and unconventional articles on Grantland, but not controversial or mean articles. Grantland writers weren’t real outsiders, but they wrote as if they were.