The case for Simmons as a Level 2 journalist is a long list:
He's the only journalist on the list to have a nickname, and that should count for something. He started posting his thoughts online as the Boston Sports Guy in 1997, when blog wasn't even a word yet. He's a pioneer of the "from a fan's point of view" style of writing. Biased and passionate, Simmons was unique among writers. His ability to reference pop culture was unparalleled. During his apex from 2002 to 2004, he routinely churned out a quality piece a week, sometimes two, and had readers checking his website every hour to see if a new article has popped up.
And then there's his contributions to fans: the immortal Ewing Theory, Level of Losing, the annual NBA Draft Diary, the Peyton Manning (among others) Face, in-game running diaries (since stolen by ESPN in-game chats), the Tyson/Artest Zone, the Annual NBA Trade Value column, the Atrocious GM Summit, Mailbags (actual emails from actual fans, baby!), Weekyl NFL picks (You know, if gambling were legal), Mount Rushmore of
And those were only the ones that made it with fans (more on that later).
In only 12 years, he's already amassed millions of readers (some may even be fans, a rarity for sports journalists)... and counting. So why isn't the Boston Sports Guy ranked higher?
Well, you really have to put his career in perspective. From 1997 to 2001, Simmons wrote two to three columns a week on his own website. Sure, that's a lot of writing, but his readers were all die-hard Boston Red Sox/Celtics/Patriots/Bruins and wrestling fans. If you are evaluating him for the pyramid, you have to look at post 2001 numbers.
Did his rise as a sports columnist in 2001/2 coincide with the underdog New England Patriots winning the SuperBowl, with the Ewing Theory almost being changed to the Bledsoe Theory? You bet! What about the Red Sox, who were competitive enough to be an interesting topic to write and read about, but not enough to advance past the Yankees (in fact, the harder the Red Sox fell ('99, '01), the better the reaction of Simmon readers)? And then there's the Celtics, who were such an inept team even after they finally dropped the Rick "Larry Bird is not walking through that door, Kevin McHale is not walking through that door" Pitino. In 2001, they drafted Joe Johnson, Kedrick Brown, and then Joe Forte (thanks, Red, ahead of Parker), then traded the only blue chip (Johnson). What about the Bruins... oh, who am I kidding, the Bruins did nothing to enhance Mr. Simmons' career.
Coincidences all in Simmons' favor? I say yes.
Speaking of coincidences, more things to put into perspective: his apex from 2002 to 2004 happened the same time where he moved to LA to work on Jimmy Kimmel's staff. Hollywood, where osmosis happens. Simmons benefited immensely from hanging out with other fellow writers much like players from the '86 Celtics benefited from the Bird/Walton osmosis.
And the drop off after 2004? Well, to put it simply, the Boston Sports Guy became the Sports Guy. He left Jimmy Kimmels show where his colleagues constantly challenged him to become better and then joined ESPN to work with the very people that he has always dispised - sports journalists who report in an unbiased way. Suddenly, there's self sensorship - Simmons lamented that "certain promises were not kept" by ESPN and that ESPN "won't let me be me" (cry me a river please), there's pod-casts, and, the worst, there're less columns. Isn't this Scott Templeton in The Wire where a news writer just wants to be on better media mediums such as radios and TVs? I'm not saying Simmons made anything up... but his aspiration is to eventually be in TV, even though he looks horrible on TV. Perhaps his role as executive producer for ESPN's 30 in 30 might finally reinvent his role with ESPN and propel him to a Level 1 guy.
When looking at Simmons' career, you also cannot ignore the fact that the entire period from 1997 to 2009 was where sports stopped being fun and started to commercialize. Sky rocketing ticket prices ($100 for Red Sox bleacher tickets!?) and unimaginable free agent signings (I don't even want to list examples here) turned the casual fan off. And many of them turned to the"from a fan's point of view" style of Bill Simmons, finding a comfort place where "someone still understood how they felt". Oh, and of course, there's this thing called the Internet that aided - understatement of the century - the popularizing of the Boston Sports Guy.
Those are all circumstantial, of course. Coincidences that, looking back, may or may not have been a valid reason for Simmon's rise to #16. I say yes, and that's that. But there are also these out-right failures: discontinued cartoon series on ESPN, incomplete all-time sports movie rankings, etc.
The biggest failure ever: losing to the Sports Gal twice in picking NFL games (and possibly many more March Madness brackets) over two seasons. Look, either you never compete with your wife or you beat her soundly. There's no middle ground here.
The second biggest failuer: openly lobbied for being the General Manager of the Milwaukee Bucks and then losing to John Hammond. Actually, maybe that was a joke. I'm not sure.
And hence his ranking at #16 and on the verge of being a level 1 guy. Quick footnote: I concede that he's career is on-going and may head for higher if he does return to his roots as a writer. Perhaps 30-in-30 will put him back on the map.
I once was a huge fan of the Boston Sports Guy. TF and I still use his definition (The toothbrush rule) to mark the date when she became my girlfriend. I used to check his website all the time to see if a new article was posted. Now? Well, in 2008, his article came behind Season 2 of Lost (see entry). That should be telling, right?
So, #16 it is for now. He can still write. I just hope it will be a column instead of more pod-casts and shows.
I will say this tho: trying to write a ranking profile for Bill Simmons made me appreciate his Book of Basketball that much more. Amazing book for NBA fans. Highly recommended - again.