Bill Simmons's Grantland Is Doomed Even Before Launch

The new website from ESPN's most popular sportswriter won't be distinct enough to draw the audience it needs


Bill Simmons won't keep his mouth shut.

And that's probably the reason he has become one of the most successful sportswriters of all time. His ability to tell a joke on the page, honed after a year and a half as a comedy writer for Jimmy Kimmel Live! and ten years as ESPN's "The Sports Guy," makes his relentless attacks on players, coaches and teams from all of the major sports the stuff of viral Web content. Today, his columns regularly receive well over one million pageviews each.

But that doesn't mean that the 41-year-old is going to make a good website editor, which is a title that he's adding to the growing list -- columnist, bestselling author, husband, father, podcaster, executive producer -- today. At noon EST the highly-anticipated Grantland launched. Billed as a "sports and pop culture website," Grantland will serve as the new home for all of Simmons's columns and podcasts and host the work of "an accomplished and diverse lineup of the Internet's leading writers and editors," according to an April press release put out by ESPN, which is funding the site as an extension of its growing digital footprint.

I'm excited to see what Simmons and his team have put together, and I'll be watching closely for at least a few weeks. But I get a little excited about every new media launch. Don't read into it. In fact, I think the new site is doomed, and I suspect ESPN's executives will recognize that in only a month or two even if they refuse to admit it until millions of dollars have been spent.

There are three major issues here and, taken together, they comprise all that there is to Grantland, except for maybe the design and the hardware on which the content is built; those servers, once scraped clean of Simmons's columns, will go on to host another site, perhaps one that stands a better chance. The problems: Bill Simmons, ESPN and the team that Bill Simmons and ESPN have assembled.

Bill Simmons

Grantland's official launch is in the future, not the past, but already Simmons himself is a little tired of the work. "It hasn't been as much fun as I had thought," he told Jonathan Mahler for a profile in this past weekend's New York Times Magazine. "I'm not sure I would do it again." Do what again? He hasn't done anything yet.

We should have expected this. Bill Simmons doesn't hold anything back -- on the page or in an interview with Mahler. If he's bored, he's going to let you know about it. (In an interesting aside in the profile, Simmons is told by his publicist not to tweet out a crack about Osama bin Laden -- "'We killed Osama and the Lakers in one week?' he suggested. 'Too far?'" The tweet isn't sent. But, of course, Simmons and his publicist had this exchange in front of a reporter knowing that it would make it into print. There, not all of his 1.4 million Twitter followers will see it, but many of them will. Maybe a few will even copy/paste that passage into their AOL email accounts and pass it around like a chain letter, a method that Simmons's early fans used in order to bypass the paywall his columns were published behind.)

Later in that same New York Times Magazine profile Mahler compares Grantland to Martha Stewart Living, "a magazine similarly constructed around a single person's market-tested sensibility." But a more apt comparison might be to the new Huffington Post as detailed in a scathing feature story by Forbes' Jeff Bercovici that dropped yesterday. "There was a bucking bronco whenever someone said, 'No, you can't do that,'" Greg Coleman, formerly chief revenue officer for Huffington Post, told Bercovici about Arianna Huffington, the site's founder and editor-in-chief. "'I know Arianna very well,' he continues. 'She wanted three things: a big bag of gold, a big fat contract, which she deserved, and ... unilateral decision making over her world. And that is where you're going to have some problems. Arianna hates to be managed."

So, too, does Bill Simmons. Mahler, who is clearly a long-time fan of Simmons and his work, even highlights the columnist's "rebellious teenager" side. In the past, Simmons has stopped work for the site and created his own blog, where he posted "at least one unedited version of his column." He's also taken to Twitter to call "the hosts of an ESPN-affiliate radio show 'deceitful scumbugs.'" That outburst led to ESPN temporarily suspending Simmons's Twitter account.

Maybe one reason that Bill Simmons hates so much to be managed is that he's never worked on the other end, he's never been a manager. And, as Huffington is struggling after going from managing a staff of about 70 to overseeing AOL's 1,300-strong newsroom, I predict Simmons will struggle as he transitions from managing a team of exactly zero to the dozen or so people responsible for Grantland.

A dozen full-time, paid staff. And paid handsomely, I'm sure, given their name recognition. It's unclear if Bill Simmons, like Huffington, asked for a big bag of gold, but he got one anyway. Which makes me question whether or not the free site will ever be able to bring in enough advertising to make it a profitable brand extension.


What is the point of launching the spin-off site in the first place even if it could bring in some extra money? This isn't going to be a new kind of content. Simmons has made it clear that the site is going to be a place for stories about sports and pop culture, two topics that ESPN already covers. The only two topics that ESPN covers, really.

If the writers can pull off what ESPN is telling us they will, then they'll be creating content that deserves to live on ESPN's existing digital pages. A smarter place to invest would have been the primary content that the Disney-owned empire is already putting out every day instead of presenting us with an alternative.

Simmons told Mahler that Grantland will be to ESPN what Miramax was to Disney, "a boutique division with more room for creativity." But ESPN is essentially telling its primary audience that its regular website and magazine aren't good enough. Or that the readers of those publications aren't good enough, anyway. On Grantland, with long-form, big-name writers, ESPN hopes to build an elite audience. The people who want to read lengthy feature stories, the conventional thinking goes, are the kind of people who want to see advertisements for fancier products. They're the kind of people who make more money and are worth more to advertisers. The suits in Bristol are betting that they'll be able to sell the Grantland audience as a premium one.

And that was clear long before a single word was written or any staffers announced. ESPN issued a press release to reveal the site's name and the press tore it up. Grantland, a reference to Grantland Rice, the early 20th century American sportswriter, reeks of pretense. "What, was taken?" Slate's Tom Scocca asked. "In other news, Simmons's podcasts will henceforth be known as 'Mercury Theatre on the Air' and his football gambling-picks columns will be retitled 'A Fan's Notes.'"

The Talent

Only a few days ago, Esquire's award-winning Chris Jones announced that he was going to stop writing regularly for the magazine and shift his attention to Grantland (Jones will remain a writer at large, a title that means something different -- or nothing at all -- depending on the publication). This news sparked another wave of interest in Simmons's new site, which first received a lot of attention in late April when ESPN set the launch date. At that time, we already knew some of the big names that the Worldwide Leader in Sports has lured to their newest project: GQ's Dan Fierman, New York magazine's Lane Brown and Jay Caspian Kang will serve as the site's top editors. Consulting editors include Malcolm Gladwell, Dave Eggers and Chuck Klosterman, no doubt all names that you recognize. (On his Slate blog, Tom Scocca referred to the three consulting editors, in that order, as glibness, naivete and ironic lowbrowism.)

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 level of talent that 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 wouldn't disagree.

In his profile, Mahler admits that he can't pick any passages from Simmons's oeuvre that would convince us to view him as the smart columnist Mahler wants us to believe he is. He relies too often on porn jokes, frat-boy schtick and tired pop culture references. But people love that. That's the essential something that makes Bill Simmons popular. He's doing something different: He's a fan and people relate to him as such. Bill doesn't sit with the other members of the press when he attends a Los Angeles Lakers game. Oh, no. Bill sits with the regular people, wildly cheering for -- or against -- players and teams. Bill doesn't even try to maintain that professional distance that others in his field do; he's friends with NBA executives and the people he tries to cover.

Here, I'll pick a couple of passages for Mahler. From Simmons's 2,400-word piece on "Macho Man" Randy Savage, who died a couple of weeks ago in a car accident: "Thanks to YouTube, his finest work endures with titles like 'Macho Man on coke' (it just seemed like it) and 'Macho Man is insane' (possibly true). He made Johnny Rodz seem predictable." What a eulogy. And on Phil Jackson: "As a Celtics fan, I couldn't have been more delighted to watch the Lakers disintegrate like that. It was like basketball porn. As a basketball fan? I hated it. That's not how Phil Jackson should have gone out."

Chris Jones doesn't write like that. But Bill Simmons might want him to. Expect another of Simmons's fits as he tries to mold Grantland into his own shape, one that will conflict with ESPN's wish to draw an elite audience and conflict with the aspirations of the writers he has attracted. If Bill Simmons wins the war and ESPN sheds some of the expensive talent it's already promised a position on the masthead, the site might eventually work. It might actually be something new.

We already have long-form websites that give us the literary. We have the New Yorker's website (which enjoyed record traffic last month with 3.7 million unique visitors according to Women's Wear Daily), we have the New York Review of Books, and we have dozens of others. Simmons has to build a long-form populist site. We're going to go long, Simmons warns his profiler. And that means, he must hope, 5,000 words on boobs. Hell, even I would read that.
But Simmons will lose this battle -- the rebellious teenager still relies too heavily on its parents for support -- and ESPN will drive this site into the ground. It's only a matter of time before he leaves. "I don't know, I think I have one more big sellout of my career," Simmons told Mahler. Well, at least ESPN didn't name the site The SimmonsPost; naming it Grantland will make it easier to extract Simmons from the venture when the time comes.

Image: ESPN's Grantland.