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Media Roundup: Bill Simmons, From Digital Cities To The White House

Love him or hate him, Bill Simmons has blazed a trail in digital sports journalism. Bruce Allen examines Simmons' local roots and how his interview with President Barack Obama further cements his role as a pioneer in online sports journalism.

When Bill Simmons had President Barack Obama on his weekly Podcast The B.S. Report this week, it marked perhaps the pinnacle of one of the most remarkable success stories the sports media world has seen.

Indeed, the former Boston Sports Guy has come a long way from writing columns for AOL's Digital Cities Boston for $50 a pop back in the late 1990's.

If you're not familiar with the story, (and if you're under 25, you may not be) Simmons graduated from Holy Cross and then got a master's degree in print journalism from Boston University. He was then hired by the Boston Herald, where he covered high school sports, and did all the grunt work young reporters are expected to do. Interestingly, among the young reporters who started around that same time were Michael Felger, Tony Massarotti, Paul Perillo and Steve Conroy - who are all still working quite successfully in the Boston sports media world.

Simmons then had a short stint at the Boston Phoenix, before, somewhat disillusioned, he worked for a time as a bartender, pondering where his future lie. He knew he wanted to be a sports columnist, but the path to that position at a newspaper was one that required as much good luck as it did years of perseverance and paying your dues in the business.

By then it was the late 1990's and the Internet was just gaining traction among the general public. Simmons hooked on with AOL's Digital City Boston to write sports columns, eventually creating his own site -

If you weren't around for those early days, it's hard to describe the impact those columns had. No one had written like this before. Each column would be eagerly awaited, and the disappointment would ripple if there was a delay in publishing them. People would cut and paste the emails and send them around to co-workers and friends. He would publish his version of the top links each day along with his own commentary on each one (Phil Mushnick hates everyone). The analogies and pop culture references were something new, and his criticism of the media and how they did their job was something that resonated with many fans, frustrated at the level of coverage they were getting of their local teams.

He eventually caught the eye of ESPN, and after a few wildly successful guest columns, was brought onto's Page 2, which is where most of a America has become familiar with him. Two books, a stint with Jimmy Kimmel Live!, and a few spats with ESPN later, he is undoubtedly the most well-known sportswriter in the country.

While he has many imitators among the younger generation of sportswriters coming up, he also has his critics, many of whom vociferously criticize each thing he writes or does. Some pick up on each factual error or mistake he makes and point it out to everyone they can reach. Some complain about the repeated pop culture references they enjoyed in the beginning, but tired of as the years went by. The launch of his Grantland site has renewed many of those complaints, even as those same critics go and read every word he writes.

While I don't agree with everything he says or writes, nor do I even read it all (It's not required, you know) I don't quite get the motivation of the "haters." If you don't enjoy something, why consume it? You've got plenty of other options out there.

He's accomplished all of this his own way. Instead of laboring as a reporter for 15 years before getting a shot at a columnist role, he created the role for himself, and not at a newspaper serving one city, but for the largest sports broadcast company in the world, where he is now among the most influential people in the industry. You have to admire that.

It's hard to know where he goes from here. A trip to the White House for an exclusive podcast with the President of the United States? From a guy who might've served you a beer 15 years ago? No matter how critical you are of his work, that is a remarkable journey.

What's next? The Sports Guy movie? I wouldn't rule it out.