Human life is complicated and messy. Accordingly, so is sportswriting and the subsequent attempt to assess sportswriters.

Anyone who puts views on paper or in cyberspace for a living is constantly subjecting himself (or herself) to criticism. “I could write that column better than you” is a reaction which any writer has encountered, given any appreciable degree of longevity. It is therefore with some degree of irony that as someone who often felt he could write a lot more thoughtfully about tennis and college football than Simmons ever did, I must confess that Simmons proved his point about the NBA and its decision-makers.

Bill Simmons really could run some NBA teams better than the current power structures in place. This, in many ways, is a core reason why Simmons’s career has become such a success, and why we’re all talking about him on the day of his announced breakup with ESPN, covered at Bloguin partner site Awful Announcing. 

The runaway success enjoyed by Simmons is not unlike the success of ESPN, as Newsweek contributor and Medium Happy publisher John Walters noted here:

Beyond talent and work ethic, though, Simmons’s work had to resonate with his audience in order for him to become a leading voice in American sports media. One can be very talented and manifest said talent, yet still fail to hit the sweet spot with a broad readership. Simmons managed to forge that essential connection, and the story of that particular breakthrough can be approached from many angles. It just so happens to be that the NBA and professional basketball showcased Simmons’s writing in the best possible light.

Why, though — why did the NBA magnify Simmons’s talents? That’s in many ways what this piece intends to explore.

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The man who first made a name for himself as The (Boston) Sports Guy was able to write copious amounts of words on the Boston Celtics and on the 1980s, the NBA’s most glorious decade. (Side note: Crossover Chronicles writer Joseph Nardone captured the first great NBA moment of the 1980s in this piece, inspired by the rash of high-profile injuries that have affected the tenor of the 2015 playoffs.) 

Simmons’s colorful and culture-heavy writing was most readily transferrable to the NBA because Simmons studied and followed pro basketball more closely than other team sports. Simmons, for all his “regular-guy” or “man-cave-dwelling” dimensions, read up on basketball and how to write about basketball. He memorably pointed to David Halberstam’s seminal basketball book, The Breaks Of The Game, as the gold standard for how to understand the workings of a professional basketball team.

We don’t think of Simmons as the scholarly type, and it’s not as though his hoops writing — especially in The Book of Basketball — was beyond criticism or reproach. However, Simmons could write about the NBA at a greater depth, and with more granular precision, than other team sports. Readers recognized this. The Ewing Theory, after all, did not come from football or baseball or hockey. Pro basketball inspired more of Simmons’ signature creativity than other team sports did.

It is not an accident that Simmons — despite being thin-skinned on the air, especially in his awkward coexistence with ESPN’s Sage Steele — found his way onto studio sets at the NBA Finals and the draft. It is not a mere coincidence that Simmons hosted the Grantland Basketball Hour as opposed to the Grantland Football Hour or a baseball equivalent. Writers have to crank out compelling, original content on a relentlessly regular basis, and Simmons was never more able to do this than when he wrote about the NBA.

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Because Simmons was so fluent in articulating the language of basketball, and in understanding the dynamics governing NBA teams, his creativity and talent spilled out in full flower when discussing the nuances of professional basketball, on and off the court. Simmons’s more cultivated voice on pro hoops — married with his wisecracking and ample pop-culture references — enabled him to become what all writers wish to become: someone who was both respected for his knowledge and enjoyed for the quality of his presentation. Simmons basically became the perfect figure skater, scoring high marks for both technical merit and artistic impression.

Knowledge of the sport got readers in the door in droves. The witty cultural packaging kept those readers coming back in droves.

We now get to the heart of the matter: At no point in his long sportswriting career for ESPN — whether in the old Page 2 days or in his more recent incarnation as the publisher of Grantland — was Simmons more comfortable than when he punctured various NBA organizations and their management groups. Showing how and why NBA teams butchered trades or missed the mark on draft night were Simmons staples — he was never more in his element than when he essentially told the world, “I could do better than some of these guys.”

What’s the foremost example of this pattern, repeated throughout Simmons’s ESPN career?

In a word, “KAHHHHHHHHHHHHHHHHHHHHHNNNNNNNNNNNNNNNNNN!”

Simmons’s fight with Minnesota Timberwolf general manager David Kahn was emblematic of The Sports Guy’s style. It was resonant. It was unforgettable. It touched a funny bone. Most centrally, like all great comedic writing, it contained a substantial core of truth. This speaks to Simmons’s best attempts at humor — they were grounded in a part of the sports world that was unmistakably real. If Simmons trotted out intended laugh lines that didn’t match what was happening in the actual course of human events, he wouldn’t have built the following he established.

On the many occasions when Simmons essentially said he could have done better than the actual decision-makers at different NBA organizations (the T-Wolves and the Milwaukee Bucks standing out from the crowd), he showed us why he was saying what he said. He made us believe it.

In many cases, he wasn’t wrong… and still isn’t.

Billy King in Brooklyn. The Sacramento Kings. The Knicks in the James Dolan era. These are the foremost examples of horribly-run organizations. It’s not that Simmons is a genius — that’s not the intended point, not even the point as Simmons has seen it over the years. The point is that some NBA organizations are really stupid, that they set the bar really low — not that Simmons could set the bar really high.

Simmons’s irreverent presentation of such a reality felt liberating for many people to read.

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It has to feel empowering in a certain way when a popular national media voice — even if an anti-establishment one such as Bill Simmons — tells you the one thing you’ve been inwardly telling yourself (and perhaps a few close buddies) for years: “I COULD RUN THIS TEAM BETTER!”

Simmons staked out that territory in his writing. He went there, he stayed there, he defended his turf, and he was always willing to elaborate on his thoughts instead of feeling he had something to hide.

Bill Simmons truly did empower readers, as shown in the runaway success (and the voluminous quality) of his mailbags. That he also proved a point about NBA organizations shows just how much of an impact he’s had on sports blogging in general, but professional basketball blogging in particular.