Why Grantland May Ultimately Hurt Bill Simmons

Bill Simmons is the ultimate hustler. In this context, hustler carries a mostly positive connotation, describing a man who has turned so little into so much.

Bill Simmons is not one of the richest and most popular sports writers because of his credentials or education. He graduated from the College of the Holy Cross in 1992 with a Bachelor’s Degree in Political Science. To be fair, he was affiliated with the school paper, first writing a column before becoming the sports editor. And he did briefly work for the Boston Herald, a job that, if it accomplished anything, informed Simmons that he would not be interested in a career in sports journalism.

Instead, Simmons parlayed his love of sports into self-employment as an internet columnist, sharing a similar level of experience with his medium. It began on AOL, a primitive life form attempting to evolve. Simmons wrote and wrote, a mixture of snark and wit, cultivating an audience he was aware existed, but was unable to go about finding it. Those early columns, written in the same underdeveloped prose as one might find here, were emailed to friends, who then in turn continued the chain. Eventually, those occupying the last links contacted the leader, the circle completed, the audience steadily building.

Simmons, a sports writer through and through, focused on regional action, what he knew, where he felt safe. Being from Boston has its advantages, nightly events occupying his time, his mind, and his attention. His style was built on a sense of readability, a common shared experience between author and reader. These were “regular guys”, average fans who did not want to become inundated with the players, the statistics, the intricacies of the games they were transfixed by. Simmons kept a safe distance from the games he so thoroughly enjoyed, cementing his reputation and expanding his network of adorning fans.

Eventually, as is every internet sports writer’s dream, ESPN became aware, a column of unobstructed snark targeting the network impossible not to notice…or put down. His contract called for three guest columns, he would later work for the online version of the sports (and entertainment) powerhouse, still currently nestled away inside the Disney bubble.

As his resources grew, Bill Simmons continued to carve out his niche of blatant, every-man homerism. His audience, attracted to his tone, his content and his wit, ballooned alongside his exposure. Bill Simmons bet (nearly) everything he had that the internet would be more than a fad, and he has cashed in ever since.

Again, to his credit, Simmons has not rested on his laurels, anchoring a bi-weekly column until the words would simply not flow. He temporarily quit to work on the first season of Jimmy Kimmel Live! in 2002, writing sparingly for ESPN as he attempted to prove his comedy chops. He worked for the show for approximately 18 months, tired of comedy and ready to regain his place in sports comedy.

His already large audience increased even further, giving Simmons some clout at the company. He could begin to push the envelope that was often sealed by socially conscious editors who refused profanity in the name of public courtesy. Enraged, Simmons became one of the first (in the very insular internet sports world) to bite the hand that had fed his ego, shaming ESPN to his millions of readers. The comments were not indecent, so they stood, if only momentarily, etched forever in the annals of internet history. Simmons has been suspended, forced to disengage from his readership, who often hang on every one of the 140 characters that he frequently uses to communicate directly.

His social presence, his man-of-the-people attitude, earned Simmons a hefty raise in 2010 (reportedly in the millions of dollars per year). His success in publishing — both of his books were New York Times bestsellers — and producing — he is credited as the creator of the 30 for 30 sports documentary series and his podcast, The B.S. Report, generates more than two million downloads per month — made Simmons a valuable asset for any network, let alone the largest entity in sports.

At a severe advantage during negotiations, Simmons asked for the ability to create his own website, linked to his parent company, but still a separate entity. He would be allowed to curse, if only for cursing’s sake. He would be allowed to hire his own talent, cultivate the internet as he had in 2001, but this time he would be looking for his proteges, his roster chock full of All Star writers.
The website, Grantland.com, launched in June of 2011, with high expectations and even higher overhead. It was billed as a chance to rewrite how the internet treats entertainment — for clarity’s sake, sports are included in this (very) broad scope — hearkening back to an imaginary time when long-form journalism was not only the norm, but celebrated as such. Grantland would be a palate cleanser designed to wipe away the 300 to 500 word articles, affectionately known as blogs, that dominated the space due to high volume and targeted headlines. Grantland would be counter-programming, sacrificing speed and volume for reporting and storytelling. It was another example of Simmons recognizing untapped potential and taking the initiative to give his perceived audience what it wanted.

Grantland is an unmitigated success. Advertising revenue has alone kept the website profitable, while page views have slowly increased. Built under the pretense of an oligarchical dictatorship, with Simmons and ESPN ruling with a cold beer, Grantland has succeeded in letting its writing staff create and curate their own personalities and audiences, tapping into the wide world of entertainment. While long-form pieces are in the severe minority, instead replaced by the 300 to 500 word articles found on competitor’s websites, Grantland has come to define Bill Simmons. Only that definition has been eroded by this new venture, that the Bill Simmons of old may never return.

Surrounding yourself with writers often more capable than yourself is a fantastic study in medieval suicide. Keeping their breadth withing a confided arena can mitigate that potential disaster, at least to a certain extent, but eventually, cracks will begin to show in your facade. Simmons hired sports writers, each with a specific sport to cover, students of a particular game with rules and intricacies so specific, they cannot begin to reach outside their scope. He hired entertainment writers, individuals who watched movies and television for a living, so as not to discover they also watched sports. His ill-fated attempt at expressing cinema in sports terminology went about as well as expected and he has yet to intentionally expose his lack of current film knowledge since. A separate-but-equal philosophy ensured that Simmons would have control over his special brand of content, able to pick and choose which topics to discuss because every topic had already been approached by another on his staff.

More entrenched than ever, Simmons would appear to remain on the outside, rooting for Boston from court-side seats at any event he desired to attend. His columns would maintain their charm, a rudimentary series of analogies to specific movies (The Shawshank Redemption and Boogie Nights) humorous enough to distract from the fact that the analogy was necessary in the first place.

Only now that he was completely inside the system, the columns became difficult to write. The frequency declined, in favor of B.S. Reports that captured Simmons’ love to talk, most frequently about basketball and football. Recently, Simmons has put together a streak that would probably fit inside one of his many sports theories, time-honored traditions that explain every nuance. His most recent columns suffered from what would appear to be extreme laziness, opting to answer emails for weeks on end.

It is here where Simmons has become defined by Grantland, the Hungary to ESPN’s Nazi Germany. By building such an impressive lineup of talent, it becomes apparent that Simmons, despite the decade he has devoted to sports writing, knows little about the actual sports, or at least appears to. Both the NBA and NFL are a series of intricate set plays that require time, sequencing, development and attrition. The statistics dictate the patterns, the true story behind each 48- or 60-minute contest. Current NBA writer for Grantland, Zach Lowe, studies game tape, dissects plays and charts efficiency, hoping to understand the many facets that make the game so special. Simmons seemingly wants to remove statistics altogether, opting for character assessment and theory creation rather than fully committing to learning the game.

For example, here is an exchange between Lowe and Simmons regarding the NBA trade deadline last week:

Lowe (3:07 p.m.): It’s over. Whew. Sifting through all these last-minute deals — Anthony Morrow to Dallas, Eric Maynor to Portland, where he’ll actually be a major upgrade to the league’s worst bench — the headliner of the day is J.J. Redick to Milwaukee in what appears to be an eight-player, three-team deal, with the Bobcats also involved.

Simmons (3:09 p.m.): In other words, we won’t be bouncing our grandkids on our laps someday and telling them about Trade Deadline 2013. I’m glad Presti finally dealt Maynor … that means our long national nightmare of Presti trying to pull a Jedi Mind Trick on the media and pretend Maynor was good at basketball and had genuine trade value is finally over. That totally would have worked if writers and other GMs didn’t have League Pass and NBA Broadband.

Lowe (3:13 p.m.): I liked the Thunder snagging Ronnie Brewer from the Knicks for a second-round pick. I’m not sure what happened to Brewer in New York. He started off defending well in killer small lineups, getting baskets on cuts, and even making corner 3s. The 3s weren’t going to last, and he did suffer a couple of bumps and bruises, but he could still do that other stuff for a team that could use some healthy, stout wing guys. The Knicks are now counting very heavily on Iman Shumpert and a slumping Jason Kidd — on both ends — and need all the wing depth they can get to play heavy minutes with Melo at power forward. So that bears watching.

Simmons (3:16 p.m.): Jason Kidd isn’t slumping … he’s old. He’s like four years younger than me, and I have to rub elk semen on my knees just to play pickup hoops once a week. Remind me to buy deer antler spray; I keep forgetting. Anyway, keep going.

Lowe (3:17 p.m.): The Thunder have never really had a full-time backup small forward for Kevin Durant. Thabo Sefolosha has basically assumed that role in the playoffs, and he wasn’t big enough to guard LeBron James in the Finals. DeAndre Liggins and Perry Jones aren’t going to be ready in June. Brewer may not impact the Thunder at all, but he’s worth a shot as a backup defense-first wing and potential extra ingredient in small lineups with Durant at power forward.

The differences in tone, diction and analysis are remarkable. Lowe offers analysis as to why each trade was made. Simmons makes a Star Wars joke and then discusses elk semen. This was actually written in a “column”, his only analysis on the trade deadline of his favorite sport for Grantland (he posted a podcast, which in full disclosure, I have not listened to).

Simmons has hired a crack squad of writers to educate him (and his readers) on sports, whether the duties fall to Jonah Keri for MLB, Bill Barnwell for the NFL or Katie Baker for the NHL. The sales pitch for Grantland should be “Come for Bill Simmons, stay for actual analysis and research conducted by highly trained professionals”. Grantland has exposed Bill Simmons for what he is: under-qualified to write about sports that do not carry a connection to Massachusetts.

This trend will most likely continue, halfhearted columns once a week that discuss how Simmons views the sports world through the lens of a man who has worked so long to establish himself as an outsider that he truly has become one. I am an unabashed fan of Bill Simmons, the man who can still write in an easily-digested manner about sports. I have listened to his podcast, occasionally watched him on the NBA pregame show on ESPN and I have seen most of the spectacular 30 for 30 series. Bill Simmons has the ability to write engaging, thought-provoking articles that mix analysis with the shtick that has brought a certain level of fame and an even greater element of success.

Tom Brady signed a contract extension on Monday that will effectively save the New England Patriots cap space so that the team can attempt to resign its free agent players. The move was deemed as a noble act by a franchise player who wants nothing more than for his team to win. In his eyes, Simmons believes he shares many similar qualities; a certain underdog mentality that both have overcome to reach the pinnacle of their profession. Unless more important news breaks over the remainder of the week, Simmons will likely pen a column on his current favorite player in the NFL and his incredible act of nobility. It will be mediocre, a sign of the times, of a man who may simply be unable to write as he once did, a man lapped by his peers who have entered the landscape armed with provable information.

Bill Simmons does share a certain quality with Brady, a desire to see his team succeed. Grantland is linked to Simmons, but his presence alone will not build its impact. The deep roster plucked from the internet will aid Simmons in achieving glory while he plays the role of the motivator, putting out content as a service to his audience, rather than to himself.

If Tom Brady is still playing at the age of 43, which Bill Simmons is now, he may share more in common with the man who enjoys rooting for his favorite team every Sunday. When that day comes, expect Simmons to link Brady to a particular theory that defines his every move. He will be expected to, and unlike Andy Dufrense, he will not be able to escape.