Bill Simmons's Humble Beginnings: Yup, This Is Our Writer

You may have caught the New York Times Magazine‘s piece on Bill Simmons this weekend. Dubbing Simmons as “the most prominent sportswriter in America,” writer Jonathan Mahler told the tale of the Boston Sports Guy’s rise to fame and fortune. If you’re not familiar with Simmons’s back-story, it’s worth a read.

Folks who’ve been following Simmons for a while, though, probably won’t learn too much from the piece. Really, a strange side-effect of being a regular Bill Simmons reader is that you find that you know an awful lot about him. For instance, I know that he calls his son “the CEO” and that the CEO usually wakes up very early. That’s sort of weird, right? One thing that the Times Magazine story briefly touches on — and that Simmons followers know well by now — is that the ESPN luminary was, early on in his career, a frustrated Boston Herald sportswriter. He was stuck covering high school sports and despaired that he’d be marooned on the lowest rungs forever. “The only one way to get a column back then was to go through this whole ridiculous minor-league-newspaper system and then kind of hope that other people died,” he told Mahler.

But how promising a young sportswriter was Simmons? A few years ago, when I was doing research for a short story on Swampscott’s Todd McShay (now an NFL draft guru for ESPN), I tripped across a high school football roundup Simmons wrote in 1994, back in his days as a lowly Herald reporter. It’s vintage Simmons, which is to say, you can see why things didn’t work out at the Herald. You have to pay the paper’s archive fee to view it in whole, but the story began:

The Northeastern Conference was wilder than “Melrose Place” yesterday, as three games with playoff implications turned into nailbiters:

In the best game of the day, Swampscott’s Todd McShay and Lynn English’s Chris Connelly staged their own version of the arms talks as visiting Swampscott (2-0) squeezed out a 19-14 win.

After Connelly tossed a 13-yard scoring strike to Nate Brown to pull English to a 7-7 second-quarter tie, McShay (10-of-17, 173 yards) answered with a 52-yard touchdown pass to Brendan Nolan. The Big Blue’s franchise tailback, Mike Madden (86 yards rushing, 2 touchdowns), then followed with a 21-yard jaunt to make the score 19-7.

Pretty perfect, right? Funny how the same instincts that made Simmons cringe-inducing as a beat-man are what have made him “the most prominent sportswriter in America” today.