Bill Simmons Will Not Die in Peace

A couple of months ago, a men’s magazine asked me to write a profile of the sportswriter Bill Simmons. The story idea was prompted by the public feud Simmons and his employer (ESPN) had gotten into earlier this year, but the piece was also meant to include classic elements of career-retrospective profile. Set up who Simmons is, why he’s important, find out where his head is now, etc.

Because I’ve been a fan of Simmons for a number of years and because I think his book, NOW I CAN DIE IN PEACE, is one of the funniest sports books ever written, I was pretty excited about the assignment. After putting in calls to Simmons’ agent and a PR rep from ESPN to set up an interview, I began doing a bunch of research and writing notes and little disjointed chunks of copy. This is my basic SOP when doing profiles. Do a ton of research. Come up with two or three angles that might or might not end up being the approach to the finished piece. Write up a ton of questions, pose them to the person in the interview, go back and decide which of my assumptions were right, which were wrong, and write the piece using a bunch of interview quotes to help support or refute my original points.

Alas, six weeks into this process, Simmons (after some back and forth with ESPN) declined to be interviewed (for reasons discussed below). Not having access to the person being written about puts writers and publications in tricky territory and in this case the magazine decided that without Simmons’ participation, the parts about his testy relationship with ESPN would be especially tough to pull off. The whole piece was killed before it ever really got off the ground.

Despite understanding the magazine’s decision, I was nevertheless disappointed, not the least because I had about 8,000 words of a half-written profile I’d spent a lot of time putting together. I hate wasting time and effort, and I also felt that during the process (including re-reading his book) I’d come to appreciate Simmons in a way I previously hadn’t. And then I remembered I hadn’t posted anything on this site for a while (been in India this summer; more on that later), so rather than let a lot of time and energy and perhaps a modest amount of insight go to waste, I wrote up the Simmons’ story, sans its star. My original hope was to get Simmons to annotate the story with quotes, sort of the gimmick he uses in NOW I CAN DIE IN PEACE, but for now here’s the “killed” story on the best American sportswriter of the decade. CT

HED: Bill Simmons Will Not Die in Peace

DEK: Ripped in the press. Censored by his bosses. Betrayed by supporters. How long until the most famous sports fan in America throws in the towel?

Find a guy who grew up fixated on something specific—music, cars, hammers and nails—then saddle up in a bar next to the backup guitarist, the shop mechanic, the CAD-zombie architect. You’ll hear it before the first beer’s gone—nothing sucks the fun out of something you love like repetition and obligation. Like many before him though, Bill Simmons, the most important sportswriter of the new century, figured he could play by his own rules. Thought he’d hit on a way to turn his obsession into his profession and not get burned by the switch. Thought he could game the system.

Simmons’ love was sports and his idea was to live the dream for all of us. If he couldn’t be a professional athlete, he’d be the next best thing—a professional fan. With an innovative writing style, and helpful kick from an emerging communications behemoth, he’d skip right over the conventional model of objective “sportswriter” by taking his hometown Boston Red Sox, the NBA, and the plainly obvious connections between game three of 1987 Stanley Cup Finals, the surprising lack of decent bars outside Yankee Stadium, and Beverly Hills, 90210, and spin it all into a career that essentially amounted to publicly rooting for his favorite teams.

Simmons’ ticket out of the suburban white guy, nine-to-five ghetto was a prodigious writing talent. To co-opt the vernacular of his style, the kid hit the keys like Clubber Lang coming out like a house on fire in the first fight against a bloated, unprepared champ. With its searing humor and unapologetic Sawx cheerleading, The Boston Sports Guy, the one-man website he started in 1997, drew the 28-year-old a growing number of devotees. One of them, Jimmy Kimmel, brought him out to L.A. in 2002 to write jokes for his TV show. By 2003, Simmons had moved on to become the full-time Sports Guy,’s most popular columnist, a platform from which he quickly seized the mantle of America’s Biggest Sports Fan from Chris Berman.

Simmons became sports’ first Internet star. Before The Sports Guy, professional athletics were written about in a vacuum, as though nothing else existed outside the arena. Simmons’ instant-classic columns, like his dead-on dissection of Hoosiers, placed sports within a broader social context, inserting them seamlessly (why had this not been done before?) into the entire mainstream milieu in a way that millions of young guys instantly identified with. His murderously funny recap of the 2006 NBA All Star Game in Houston—aka “the black Super Bowl”—concluded with Michael Jordan’s wife breaking up a raucous hotel-bar card game: “She sneaks in and sits down next to him. And poor MJ looks like somebody who took a no-hitter into the ninth, then gave up a triple off the left-field wall.” Columns like these spoke to fans with such universal empathy that they stand beside anything Grantland Rice or George Plimpton ever wrote.

I personally know a writer is great when he can get me to read and laugh at all 374 pages on a subject I hate—in this case, the Red Sox and the miracle run of Boston sports dominance the rest of the nation has been enduring alongside the worst presidential administration in history. (I’m not saying there’s a connection, but I’m not saying there isn’t, especially given Curt Schilling’s repulsive and needlessly divisive public endorsement of Herr Bush immediately after the 2004 World Series.) In addition to being ridiculously funny, Simmons’ account of the Sox’ curse-killing Series triumph, Now I Can Die in Peace, is one of the three best sports books of the modern era, alongside Jim Bouton’s Ball Four and Joe Queenan’s True Believers.


If you’re a sports fan, or if you’ve been paying any kind of attention to the career arc of media darlings, you know what happens next. Get famous enough and pretty soon people will start hating you simply for being a celebrity. For Simmons, the backlash began in earnest during March Madness 2006, when a Sports Illustrated feature on Internet sports websites portrayed him as the field general for a style of sub-literate, frat-boy, turd journalism with less credibility than a North Korean presidential election. Web postings dedicated to Simmons antipathy blossomed, typified by the Anti-Bill Simmons blog, which continues to rip Simmons despite aping his signature style. On the eve of last season’s Celtics-Lakers NBA Finals, when all of Boston was wrapped in a euphoric group hug of disbelief (“The Pats? The Sox? The Celts? What’s next, Scarlett Johansson comes over to give us all blowjobs?”), longtime sportswriter Bob Ryan (who Simmons thanked in the acknowledgments of his book) devoted an entire Boston Globe column to annihilating Simmons. The piece began with the sentence, “Beware of False Prophets.”

Outside criticism is one thing, but from the day he signed with ESPN, Simmons has also famously struggled with pleasing corporate masters who frown upon such Simmons specialties as toxic excoriation of the network’s most inept announcers. All of this professional strain exploded into public spectacle this past spring when the beleaguered Simmons announced that he’d be cutting back on the number of columns he writes for by way of protesting the Disney-owned company’s censorship of his work. Simmons had recently signed a major contract extension with ESPN through 2010, but now he claimed the company was reneging on its deal and editing his best jokes, telling “I still love writing my column and only re-signed last year because I really did believe that we had hashed out all the behind the scenes bullshit and come to some sort of agreement on creative lines, media criticism rules, the promotion of the column and everything else on Within a few months, all of those things changed and certain promises were not kept.”
If you’re curious about the kind of material the worldwide leader considers inappropriate for you and other impressionable children, Simmons provides an example in Now I Can Die in Peace as part of a discussion on the creative use of profanity at Fenway Park. “My favorite shirt that I wasn’t allowed to mention at The one that says ‘Yankees suck’ on the front and ‘Jeter swallows’ on the back. Now THAT’S comedy.”
For a guy in the smart-aleck business, depriving readers of laughs is never wise, but the highly publicized dustup with ESPN may have hurt Simmons’ image more than the company’s. The smattering of onetime fans turning on their former hero has lately begun to feel like a sea change, with readers beginning to wonder if sandbagging his column doesn’t put Simmons in the company of diva athletes who cheat the fans by loafing after fly balls or refusing to take their allotted twenty-five jumpers a game just to prove a few pissy points to management. The gathering mood was summed up by one ex-fan in a web posting succinctly titled, “Bill Simmons is a Twat.”
Another of those ex-fans is my buddy Shanghai Bob, a man who follows American sports with the obsessive fervor characteristic of homesick expats yearning for familiar touchstones amid the chaos of Southeast Asia. Shanghai Bob’s far-flung residence makes him precisely the type of reader Internet columnists are built to reach and for a number of years he and I giddily forwarded each other links to stories with subject lines like “Simmons does it again!” Shanghai Bob stopped with the Sports Guy emails a couple years ago and lately has taken to referring to Simmons as “that little punk from Boston.” A few weeks ago, I emailed Bob to find out why exactly he’d soured on the guy.

“I vividly recall a three-page sponge bath and neck rub of Curt Schilling published long after the 2004 Series when it might at least have been understandable,” he replied. “Without doubt the most nauseating piece of jock-sniffing ever composed.”

Kidlike adoration of athletes is part of Simmons’ shtick, but his relentless Beantown boosterism was bound to get old with a national audience. It hasn’t helped that with their teams’ ascendancy Boston fans have morphed into the most obnoxious lot this side of an Arsenal football riot, remarkable for being the sole entity on the planet capable of making a sympathetic figure out of Hank Steinbrenner. Most of this is due to the city’s insufferable run of sports success, but Simmons shares the blame for playing a not insignificant role in rallying the quaint, mythical notion of something called Red Sox Nation into a cohesive conglomeration the rest of the country now despises in a way it had not previously realized was necessary.

After the somewhat predictable “Fuck Boston” rant, Shanghai Bob moved to the other chief criticism of Simmons, that the man often simply doesn’t know what he’s talking about. A prime example (provided by my Simmons-hating friend Rama in New York) is this exchange between Simmons and ESPN NBA “draft guru” Chad Ford following Ford’s critical review of several European players during an online debate.

Simmons: Wait a second, aren’t you the same guy who keeps pushing that superduperstiff Kosta Koufos on us as a potential lottery pick?

Ford: Ummm … Kosta Koufos was born in the exotic locale of Canton, Ohio. He’s played American basketball his entire life. Yes, his parents are Greek … but does that now count as international?

Simmons: Kosta Koufos is American??? My whole world has been shattered! Can we count him as a foreigner, anyway? Come on, throw me a bone.

While the view that Simmons doesn’t have a clue about certain subjects is occasionally valid—Ryan essentially made the same point, though less effectively given that his tone suggested a man being prepped for a hip replacement—this criticism has never made sense to me. Simmons is without question a blowhard (to my ear, the lovable kind, but I understand dissenting opinions) and like all columnists he plays fast and loose with rhetoric to support his various outrageous arguments. But his rise to fame was facilitated not by a keen grasp of numbers or precedent (though more often than not he has that), but rather by a unique recognition of how sports fit into the fuzzier realm of the prevailing cultural zeitgeist.

On this last point, however, there’s also cause for concern. Throughout his career Simmons has been obsessed with growing old and irrelevant, telling The New York Times in 2005, “I live in fear; fear of being tapped out,” and Sports Illustrated in 2006, “I really feel like I have a year or a good eighteen to twenty months left in me.” By way of keeping fresh, he’s replaced the 90210 jokes with references to The Hills and The O.C., but more and more often he’s been misreading the landscape in more fundamental ways. Previewing Wimbledon in his ESPN magazine column this year, he essentially declared the entire sport of tennis dead. “If I guaranteed you that the 2008 Wimbledon men’s final would be the best match of the past 20 years, would you watch it?” he wrote. “Amazingly, many sports fans would say no.”

Rafael Nadal’s epic finals triumph over Roger Federer, of course, turned out to be perhaps the greatest tennis match ever, one of those transcendent TV events, like the Boise State-Oklahoma Fiesta Bowl, during which energized fans texted and emailed like-minded friends around the country until, even before it was over, the match had passed into the realm of legend. And plenty of people watched it. NBC pulled a twelve-percent share of the total TV audience, a forty-three percent increase from the year before. Two years in the making, Federer’s dethroning was the apex of one of the most ferocious rivalries in contemporary sports yet Nadal hadn’t even been mentioned in Simmons’ column.


Actors and musicians have reputations for being difficult interviews, but the fact is that, dating back to the days of Howard Cosell and then Bryant Gumbel, no one in the celebrity universe is as big a prima donna as the sports media celebrity. (Bob Costas being a rare, holy exception.) Employed by a media company that was a major sponsor of his radio show, I once spent six months unsuccessfully trying to track down Jim Rome, cock-blocked at every turn by an army of protective minions reminiscent of David Spade as Dick Clark’s personal assistant on Saturday Night Live. “And you would be? And this would be regarding?” “Uh, the same guy who’s been jumping through your fax-phone-and-email hoops for the past six months trying to arrange an interview with the guy we dropped a quarter of a million bucks on this year.”

Back when he was hosting Around the Horn, I flew to Washington, DC to interview Max Kellerman. The rising ESPN star postponed our first scheduled meeting, then a second, and I spent three days in a hotel room watching the TV show he was filming half a mile away and waiting to be rescheduled. I finally went home without an audience with the media giant. Tom Hanks? A sweetheart. The allegedly temperamental Williams sisters? Graciously allowed me into their Florida home less than forty-eight hours after flying back from losses in the Australian Open. For sports guys, though, you have to grovel.

Simmons took his time ignoring interview requests for this article before eventually declining through an ESPN publicist, and a few days later with a polite, apologetic email. Since the SI story, which Simmons still sees as a hurtful ambush, he’s been wary of interviews, and extremely selective about media he talks to.

Like most of us would, Simmons has recoiled from public criticism, but the infamous SI piece wasn’t so much a hatchet job on him as it was an unintentionally comic display of insecurity and fear of the Internet by the brick-and-mortar establishment. Like all shortsighted print media (listen, the Internet is going to replace print the same way TV replaced radio and the movies), SI is scared shitless of the Internet and undoubtedly saw in Simmons’ youthful hand the dagger coming to hack the majestic treacle of its old-school sapmeister Rick Reilly into obsolescence. (Unable to beat ’em, Reilly and his cloying style merely joined Simmons at ESPN.)

The article was also notable for the scolding tone it took with supposedly unscrupulous and ill-informed Internet writers who had been the first to break the news, back in 2006 mind you, of a link between Roger Clemens and a positive steroids test. Tsk, tsk, you Wild West neophytes, finger-wagged the scooped magazine, leaving us all to wait another two years for the established, respectable media to crawl up to the story.

The SI piece was a joke to every reader under fifty, but anyone who’s ever been mauled by a bloodthirsty reporter or backstabbed by fellows in the profession will have sympathy for Simmons’ newfound suspicion of interviews. On the other hand, it’s hard to drum up sympathy for a guy who made his fortune naming names and blasting away at targets and who then signals for a time out once the pot shots come flying back at him. If Simmons didn’t want to be called out in public, maybe he shouldn’t have once described the roster of Red Sox managers in his lifetime as “a staggering collection of drunks, butt-kissers, dimwits, village idiots, senior citizens, hotheads and lunatics.” Nobody likes a guy who dishes it out but can’t take it.


I’ve never met Simmons and I could be wrong on this, but I don’t get the sense he’s a prima donna or a bad guy. But either way, I really don’t care. I don’t continue to read his stuff because I think he’s right—I read him because I find it remarkable that after so many years, after so many columns, after so many brilliant and completely justifiable Stephen A. Smith jokes have undoubtedly been cut from his copy by unimaginative corporate weasels, the man is still the funniest, most insightful sportswriter we’ve got (the Wimbledon whiff notwithstanding). I don’t say that facetiously. More than anything it’s his talent as a writer that people underestimate—Simmons is often dismissed as an Internet phenom, but the fact is he excels in books and magazines and probably the screenplay he’s occasionally mentioned writing.

That said it’s hard to account for the strange place his once brilliant career is in and a lot of Simmons’ problems seem to be of his own making. I’m glad I don’t work for a Disney-owned company and I’m sure Simmons’ columns suffer as a result of the fact that he does. But we all make compromises and having worked for ESPN before Simmons presumably signed his new contract with his eyes open. He undoubtedly enjoys the financial security (various estimates put his annual salary between $500,000 and $1 million) and status that comes with being a big wheel at ESPN, but who wouldn’t expect a deal like that to require certain concessions? Keith Olbermann isn’t at MSNBC for no reason.

It’s possible that after more than a decade of helping the public fully appreciate the social value of multi-millionaire kids with godlike fast-twitch muscles and steroid dealers on speed dial, Simmons’ current temper has much to do with the assertion his sometimes blog partner Chuck Klosterman makes in the book Sex, Drugs, and Cocoa Puffs: “Nobody realizes how much the people who write about sports despise the subject they write about.” Do something long enough, turn your love into a job, and see how fast it takes to become embittered.

Simmons repeatedly insists he’s still as big a fan as ever—making the point often enough that you begin wondering who he’s trying to convince—but all of us fell in love with sports as kids and I have a hunch that Simmons is as much a fan of his childhood as he is a fan of sports. After the table of contents, the first page of Now I Can Die in Peace features a photo of Boy Bill dressed up for Halloween as his childhood hero, Boston centerfielder Fred Lynn. It’s a sweet shot—baggy uniform, eye black smeared like butter, cockeyed Sox cap. You see a lot of love in that kid’s face. And if you look at it long enough, you can almost avoid coming to the conclusion that Simmons hasn’t become what he promised himself and tacitly promised all of us that we never would—sick of the game.

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