The Enthusiast

Bill Simmons has set a new and unbeatable standard by writing like a fan—just far better.

In the far corner of my childhood bedroom, a copy of The Bill James Historical Baseball Abstract stood out among the mishmash of baseball cards and rolled-up posters that formed the obligatory bookshelf-cum-sports-shrine. Bulky, heavy, and dense, the Abstract was forbidding. Who had the energy, or the patience, to really engage with its contents? Each page seemed to contain its own world; there was no chance I could possibly finish it. But James’s book imparted a certain gravitas to an otherwise ordinary collection. The sheer amount of knowledge a book contained was proportional to the seriousness it conveyed. Even though I hardly glanced at James before age 18, the Abstract’s mere presence was a sign that I was a step closer to adulthood than one might have rightfully concluded at first glance. More important, it was proof that sports, the thing I loved most in the world, could be taken seriously.

It is easy to say that the vast majority of sports commentary—and, indeed, the vast majority of every aspect of life that even touches on the worlds of professional and collegiate sports—is embarrassingly childish. But this understates the case, because even as a child or teenager, every thinking fan is certain to feel that the entire circus is beneath his dignity. It is not just the inane, wannabe-macho commentary during every halftime show, or the ever-present backdrop of misogyny, or the incessant beer ads that run during time-outs. By high school—at the very latest—one could surmise that a deep love of sports was meant only for dumb jocks, and was therefore incompatible with the contemplative life. What intelligent person, after all, would choose to spend his Sundays with Terry Bradshaw’s grating folksiness and Mike Ditka’s roaring bluster?

If James and Ditka represented the two poles of the sports commentariat, surely the middlebrow fan could find a middle ground. This territory was for a long time occupied by Dan Patrick and Keith Olbermann’s ESPN show, SportsCenter (and their book, The Big Show, which came along a few years later). Olbermann and Patrick registered the impressive accomplishment of making sports highlights even more compelling; yet neither had Ditka’s transparent machismo or James’s intimidating nerdiness. The brilliance of Olbermann and Patrick’s shtick was that their observations and analysis came from such a distance. Indeed, this constituted their entire mode of scrutinizing the sports universe. They probably felt the same passion as other sports fans, but their routine was so full of irony and sarcasm that they hovered above the spectacle. It was as if they, too, sensed that the wonderful world of sports was full of nothing so much as hot air, and thus the only way to preserve what they loved was to take a step backward. Why not gently mock and jeer and wink at viewers, empowering both them and yourselves in the process?

The Big Show feels dated today because Olbermann occupies such a radically different place in our culture, but also because ESPN’s television commentary has been dumbed down significantly. However, in a chapter portentously titled “How to Be a Sportscaster When You Grow Up,” the authors not only manage to outshine expectations with some enjoyable advice, they also preach the following:

Another part of the attitude adjustment may come as a shock. Do not take sports seriously. Take your work seriously: Be dedicated to it, know everything you need to know about it, enjoy it, remember that the viewer or listener may be fanatical about it—but maintain a healthy distance from it. The moment you think that a sports team or league or player is actually important, you become a servant of the “sports media complex” whose only purpose in being is to separate people from their money. Your dedication has to be to your viewer or listener, to the truth, and, lastly, and only to the degree that it does not conflict with your ethics, to the success of your employer.

MSNBC viewers will not be shocked to learn that Olbermann was the writer of this self-important passage. And yet, he neatly defines the Olbermann-Patrick ethos: artfully remain above the fray.

Olbermann and Patrick set the standard for sports commentary, even if they did not “redefine” it sufficiently (the term is taken from Bob Costas’s introduction). A legion of imitators, on both ESPN and other sports networks, did their best to mimic the anchormen’s detachment. The problem was that a smirking sense of humor can, shockingly, come across as obnoxious. Olbermann and Patrick managed to strike the right balance, but many of the next generation’s commentators were no more than smug, arrogant jerks (Costas ruefully concedes this). Despite their achievement, room remained for an entirely different approach that could still thread the needle between aggressive masculinity and statistical obsessiveness.

This might seem both rather obvious and easily attainable, but Bill Simmons threaded this needle more skillfully than his competitors. Simmons, a Boston-bred writer living in Los Angeles, is, without much question, the most popular sports columnist in America. He is extremely prolific and, for a sportswriter, quite intellectually curious. His first book, an account of the Red Sox’ miraculous 2004 season, was tellingly called Now I Can Die in Peace. His latest effort, a 700-plus-page history of the NBA, is biblically titled The Book of Basketball. From a distance, the book looks like a Tolstoy novel: its encyclopedic ambitions are clear. But as with all of Simmons’s work, it is written in (usually excellent) conversational prose and sprinkled with digressions, in-jokes, and bawdiness. It is the work of a true fan—an emotional, biased observer who seems to relish his subjectivity. Simmons might be walking the same line that Olbermann and Patrick once trod—the line that separates mathematical formulas from beer jokes (and believe me, the book contains plenty of both). But Basketball is not ironic or dispassionate. And it might just represent the next phase of sports commentary.

Simmons is known on as “The Sports Guy”; readers can be excused if this reminds them of a politician who calls himself a “man of the people.” In public, Simmons fans love to yell out “Hey, Sports Guy!”—which (again) recalls voters who, when interviewed on camera about their candidate of choice, say that he is “one of us.” To Simmons’s credit, however, the unassuming nickname actually fits him comfortably. In certain respects, the public figure that Simmons most clearly resembles is the early David Letterman, although Letterman has never tried to seem like an average guy. Still, they have one thing in common: the way they personalize their work. Letterman fills his show with in-jokes and (usually self-deprecating) personal references, but he also demands that his viewers accept what he thinks is funny. If you do not think that throwing watermelons off the roof is interesting, then you are out of luck, because Dave finds it fascinating. You rarely get the sense that Letterman’s show revolves around jokes that he himself finds boring and lowbrow. (The opposite is true of Jay Leno, a comedian canny enough to understand his audience.) Of course, this tendency is also Letterman’s greatest weakness as an entertainer (“Oprah, Uma”).

Simmons is eerily similar in this regard. If you do not recognize his pop-culture references, too bad. If you don’t like the long digressions about Teen Wolf (a mid-’80s Michael J. Fox film about basketball, for those who do not regularly read Simmons), too bad. True, Olbermann and Patrick would also make plenty of references to pop culture, but the references came across as charmingly haughty, as if the anchormen were showing us that they had interests that extended beyond the court or field. Simmons’s podcasts, now a regular feature of his ESPN page, are filled with conversations between the host and his old friends and relatives. He thinks they are interesting, and you should too. That takes a certain arrogance, but Simmons is smart enough to follow his own good instincts.

The opening pages of Now I Can Die in Peace—subtitled How the Sports Guy Found Salvation Thanks to the World Champion (Twice!) Red Sox—give a good window into Simmons’s style. Here is how he begins the book:

My editors had to dissuade me from naming this book Love Child of the Impossible Dream. The more I thought about it, they were probably right—it sounds like the title of a John Mayer album, or maybe a crappy civil rights epic starring Reese Witherspoon and Omar Epps. And we wouldn’t want that.

The second sentence here is clumsily written, which is not often true of Simmons’s prose (I’ll return to this later), but one immediately understands that we are getting Red Sox history through a very particular prism. A footnote on the first page makes the following observation:

Imagine being stuck at an all-male school in 20-degree weather? Yikes. If you’re scoring at home, Holy Cross finally started admitting women in 1972, although they didn’t start admitting women who put out until 1999.

A few pages later, however, Simmons is talking about his parents’ divorce. In other words, he gets away with (most of) his sex jokes because the reader understands perfectly well that he isn’t striving to be the toughest guy in the room. He jokes about sex because everyone jokes about sex; he has the same unfiltered quality that we expect from our friends. Similarly, his writing about his father is emotionally rich, but avoids the sentimentality that is often the gruesome complement to manly posturing (think Oliver North or Tom Clancy).

If Simmons’s first book was a personal journey through Red Sox fandom, The Book of Basketball is an even more personal travelogue through the NBA galaxy. Simmons has always loved professional basketball; he is both a passionate critic of the sport’s (and the league’s) shortcomings, and a fierce opponent of people who deplore the pro game and have a more politically correct—and misguided—preference for college basketball. Unsurprisingly (or do I mean unfortunately?), Simmons is a Celtics fan, and while his bias more than occasionally reveals itself, his enthusiasm for basketball is infectious. It is hard to summarize exactly what The Book of Basketball is: Simmons has written a guide to NBA history, a list of the 96 greatest players of all time, and a memoir of his relationship with the sport—all with his trademark humor and style. In an early footnote about Boston’s reputation for not embracing black players, he notes,

Boston’s deep-seated racial issues bubbled to the surface one year later, thanks to a divisive decision to proactively integrate Boston’s public schools and all the ugliness that followed. Although, looking back, it was probably a red flag that Reggie Smith and Jim Rice were the only black guys on the Red Sox for like 40 years and everybody was fine with this.

Even the sections of the book that most resemble a reference work are written in this same style. His player rankings begin with dense statistics, but then Simmons lets loose. Here is the opening of his mini-essay on the Dallas Mavericks forward Dirk Nowitzki, who led his team to the NBA finals in 2006, only to suffer a crushing loss:

The NBA’s alpha dog almost ended up being German. Yup, we came that close in the 2006 Playoffs—if not for the heroics of Wade, Salvatore, Payton, and others, Germany would have made its biggest advancement on American culture since David Hasselhoff infiltrated the horny brains of teenage guys with Baywatch. Personally, I was terrified—this was the same country that started two world wars and deliberately injured Pele in Victory.

(The names above belong to perennial NBA all-stars Dwyane Wade and Gary Payton; Salvatore is Bennett Salvatore, a referee who Simmons thinks is at best incompetent.) A couple of pages later, he is discussing whether to induct Nowitzki into the “42 Club,” which is named for a strange (but helpful) statistical formula that Simmons himself has created. But to get to the Jamesian formula, you first have to consume a couple of politically incorrect jokes and a reference to an early-’80s movie that, one hopes, very few people remember.

This is Simmons at his best, but his tics are occasionally irritating. The Sox’ victory “wasn’t just a lucky chain of events,” he writes.

This was like winning the lottery three different times, or better yet, like Justin Timberlake banging Britney Spears, Jessica Biel, Scarlett Johansson, and Cameron Diaz in their primes, only if he had added Lindsay Lohan, Angelina Jolie, and Katie Holmes.

These jokes, sprinkled over 700 pages, become wearying. Simmons, at times, would benefit from taking at least a half step backward and sticking to his subject matter.

Simmons’s biases are part of his charm, although his chapter comparing Wilt Chamberlain with the Boston Celtic Bill Russell could have used more objectivity. By the time he ends his case for Russell with “the defense rests,” his sometimes thoughtful insights into these two great big men have been obscured by the feeling that we are watching a show trial. He also adopts the annoying habit—perhaps from his friend Malcolm Gladwell (who wrote the book’s introduction)—of quoting statistics and telling us what to think about them, or assuming that we will draw the same conclusions from them that he does. In the same chapter, Simmons, perhaps unable to resist his better instincts, spends two pages trying to expose the “myth” that Chamberlain was a “great guy.” Well, fine. I once approached Russell at a Chinese restaurant, where he was standing alone, and told him that I was a huge admirer of his. He grunted and turned his head away. I enjoy repeating this story to my friends who are Celtics fans, but alas, I would not argue that it proves Wilt Chamberlain is the greatest center in NBA history.

Still, Simmons’s personal recollections of his favorite players are generally smart and well executed. In an especially good section on Larry Bird, he writes,

You can’t call him a superhero because he wasn’t saving lives or making the world a better place. At the same time, he possessed heroic qualities because everyone in New England bought into his invincibility. He came through too many times for us. After a while, we started expecting him to come through, and when he still came through, that’s when we were hooked for good … Unfortunately you can’t glance through Bird’s career statistics in the Official NBA Register and find the statistic for “most times the fans expected their best player to come through and he actually did.”

The tone here—personal but intellectually open-minded—is just right.

The standard rap on Simmons is that he is no more than a passionate fan who happens to be a terrific writer, and this is more or less true. His writing, over 700 pages, rarely flags—an impressive achievement considering how many sports columns stall after 700 words. Some have faulted Simmons for his lack of interest in reporting, and rightfully so. The upside of this, however, is well phrased by Gladwell:

The other part about being a fan is that a fan is always an outsider. Most sportswriters are not, by this definition, fans. They capitalize on their access to athletes. They spoke to Kobe last night, and Kobe says his finger is going to be fine. They spent three days fly-fishing with Brett Favre in March, and Brett says he’s definitely coming back for another season.

Simmons may not be removed from his passions, but he does appear remarkably distant from the sports establishment. His biases and shortcomings are the result of childhood allegiances, not off-the-record dinners with Larry Bird. He is willing to endlessly criticize athletes, and his attack on the NBA’s secretive management style and pathetic officiating continues to be his most valuable contribution as a writer. (In this same outsider spirit, Simmons divides his bibliography into books that were helpful and books that are not particularly worth reading. Not only is this useful for prospective readers, but it marks a nice break from the normal back-scratching.) The only time that I can remember seeing him completely desert common sense and succumb to old-fashioned conventional wisdom was when he decided to pile on Patriots coach Bill Belichick’s controversial decision to “go for it” on a fourth-and-two last season. But, of course, we are talking about the New England Patriots.

The danger of Simmons’s approach—for the rest of us, if not for him—is the same danger that eventually overtook ESPN after Olbermann and Patrick left. Personalized, opinionated discourse is fine, but if you cannot write as intelligently and humorously as Simmons can, you might as well leave the rest of us in peace. My guess is that 10 years from now, Simmons will come to be seen as an outlier, primarily because few people will be able to match his style and skill. Sports commentary will still be a swamp of dank bromides and unattractive aggression. “You either love sports or you don’t,” Simmons declares, tautologically, at the end of his first book, and about this proposition, he has never wavered. A love of sports is not a sufficient condition for smart sports commentary, but it very well might be a necessary one.