A large part of Simmons’ appeal has always been that sense that you knew him, that somehow you were invested in his success. Malcolm Gladwell and Chuck Klosterman will sell more books in their lifetime than Simmons, but people don’t wait in lines spanning around the block just to have them sign their book like they do for Simmons. (A search for photos of Simmons brings up hundreds of shots of him posing with fans.) …But it’s what fans have always done with Simmons, even those who purport to hate him. Simmons turned into an indie rock band from the early ’90s. “He’s hanging out with Jimmy Kimmel and Matt Damon now? SELLOUT!” We treated Simmons like he was a guy from our neighborhood who made it big, like it was important that he remember the little people who got him there. In a way, he kind of was.
Leitch is right, although of course it’s a little hard for me to have the same perspective; Leitch didn’t even read Bill on the Boston Sports Guy site in the pre-2001 era, whereas – as longtime readers will recall – I wrote on the site for over a year. I’ve been reading Bill’s stuff since we were on the college paper together in the early 1990s. While I’ve enjoyed a lot of his writings on ESPN.com, they were nothing new to me, because I knew his writing style so well by then. And given our common background at Holy Cross and how long I’ve known him, Bill basically is a guy from my neighborhood.
Leitch’s larger point, though, is one I’ve made repeatedly over the past decade about writers, politicians, musicians, and the blogosphere in general. There’s no substitute for a conversational tone that draws the reader/listener/viewer in. There’s no substitute for being truly, comfortably yourself – maybe a slightly more eloquent, witty or composed version of yourself, but people can tell when you are talking to them the way you would talk to your friends, and when you are just writing or talking at them. The latter is usually a sign that you are taking yourself too seriously and/or disrespecting your audience. I always personally feel my writing is much stronger – not just my blog writing but my legal writing as well – when it feels more conversational. Bill James was probably the first writer I really and truly absorbed that lesson from – and even to this day, James’ fans are so dedicated to the man’s work not only because of his insights, his wit and wisdom, or his scientific rigor, but because his writing was always a frank conversation where he’d go off on tangents, discuss petty feuds with his adversaries, gripe about what was on the radio, etc. You felt, just from reading the annual Abstracts, like you knew the guy. And Bill Simmons’ writing does the same thing, and thus has generated the same loyalty, especially from people who remember when Simmons, like James, was essentially self-publishing his work and living on a shoestring to do it.
It’s true, as Leitch says, that Bill has faced more backlash as the years have gone by, inevitably due to a combination of his success and ubiquity, people getting tired of his signature style, and the fact that it’s hard for a die-hard Boston fan to keep the same underdog appeal when the Red Sox, Celtics and especially Patriots are rolling up title after title. But that comes with the territory. Bill’s had great success and he’s earned it by being the sportswriter the fans wanted to be.