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Looking for the Next Bill Simmons

Last week, Paul Oberjuerge asked a question I found intriguing: Why is there only one Bill Simmons?

Oberjuerge took a tour of Yahoo, CBSSportsline and SI hoping to find another writer from the ranks of the “all-around, every-topic-is-game, 5,000-word-plus essayists.” But he found mostly sport-specific beat writers and bloggers. So where, he asked, are Simmons’ competitors?

It’s a good question, and Oberjuerge has an interesting take on the possible reasons why. His theory, briefly restated, is that the collapse of print has throttled potential competitors’ development. The up-and-coming guys who should have spent recent years honing their craft at suburban papers until they were ready to make the leap to the next level don’t exist, and the surviving print guys are entrenched folks who loathe the Web.

From a print perspective there’s some truth to that. But as a Web guy, I’d ask a different question. Looking at the makeup of most mainstream sports Web sites, the better question might be, “How did we even get one Bill Simmons?” And my answer would be that we got lucky.

Actually, we got really lucky – because I think there is indeed another writer who fits what Oberjuerge is looking for. Like Simmons, Joe Posnanski has an enormous following, covers the waterfront, is startlingly prolific, and writes frequent long-form pieces. (His blog is subtitled “Curiously Long Posts”.) And Posnanski essentially followed the blueprint Oberjuerge sets forth: He’s a newspaper veteran who embraced the Web as a place where he could write as often as he liked at whatever length he liked. Simmons, on the other hand, essentially invented himself on the Web after trying the conventional print route and feeling like he was spinning his wheels.

Which brings me to what I think is the heart of what Oberjuerge is grappling with.

Look at the rosters of writers at the Web’s top sports destinations and you’ll see that very few of them have Web pedigrees. Whether it’s the sites Oberjuerge mentions, or Fanhouse, or the rest of ESPN, or the new ESPN Locals, the ranks of both writers and editors are thick with print veterans.

I’m not saying there’s anything wrong with that. I’ve always insisted that great storytelling is great storytelling, regardless of the medium, and those sites have shook off a lot of print’s strictures. Most everybody now tweets and files in real-time, there are print writers who’ve become excellent curators (Buster Olney springs to mind), and there’s plenty of smart business sense on display. But whether in print or on the Web, the columns produced by print veterans mostly hew to print forms — the “800-word from-the-mountaintop declamations” Oberjuerge mentions. Given the print pedigrees you find everywhere, that’s not surprising – it’s the playbook most everyone at those shops internalized long ago.

But that isn’t Simmons’ tradition. Where his peers are mostly print writers who have traded ink for pixels without changing much else, he’s a pure Web guy. (I always thought Simmons’ ESPN the Magazine columns felt curiously abridged, like they ended when he was just getting rolling.) Simmons is often written about as if he’s synonymous with either ESPN or Web sports, but he’s essentially unique within both those worlds. If he were starting out today, I bet Simmons would feel just as blocked and frustrated trying to break into the established Web-sports firmament as he was trying to make his mark at the Boston Herald and the Phoenix.

So if you want to look for the next Simmons, you need to look outside the established order of the mainstream Web and print media, because for now they’re essentially the same.

Oberjuerge says he imagines there are big-picture Web guys out there, “not getting paid, living off Ramen and churning out stuff.” And I’m sure that’s true — but the nature of the Web and building a Web audience encourages people to work on a smaller canvas than that.

Yes, there are national sports sites for which any topic is game – Deadspin comes to mind, and it and the sites it inspired have brought a number of writers big audiences and book deals. But that’s a very hard recipe to follow. A better way to succeed is to find a niche – and general sports commentary is the opposite of that. Moreover, today’s trends in Web applications, advertising and traffic measurement all center around the strongly local: Instead of going for big numbers and an amorphous audience that visits occasionally, the drive is to find a smaller audience that visits a lot and desires a true connection.

So it’s no surprise that most sports bloggers begin with far more local interests and ambitions, and attract far more local audiences. But some of them are quite successful nonetheless: Oberjuerge describes the up-and-comers as “buried and lost,” but I think a lot of sports bloggers would find that puzzling. They’re making names for themselves and having a ball covering just the Big East or the Mets or Tim Tebow or walk-off wins. (And recall that this was Simmons’ original recipe: He began as the Boston Sports Guy, and his detractors often harp on his Boston loyalties.)

There will be more sports columnists who are prolific generalists. There will be columnists who take to the Web and happily escape the 800-word confines of the print tradition. But until the leaders of mainstream Web sports sites come from the Web, print writing models will predominate, and up-and-comers will find those doors just as closed as Simmons did. Meanwhile, those up-and-comers will be learning to be successful — and may find they’re perfectly happy – as the Bill Simmons of smaller realms.

Jason Fry is a freelance writer and media consultant in Brooklyn, N.Y. He spent more than 12 years at The Wall Street Journal Online, serving as a writer, columnist, editor and projects guy. While at he edited and co-wrote The Daily Fix, a daily roundup of the best sportswriting online. He blogs about the Mets at Faith and Fear in Flushing, and about the newspaper industry at Reinventing the Newsroom. Write to him at, visit him on Facebook, or follow him on Twitter.

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