Bill Simmons' Big Score

How a failed newspaper writer built a new kind of media empire at ESPN

April 29, 2014 1:00 PM ET
Bill Simmons
Bill Simmons
Chris McPherson

From Bill Simmons' fourth-row seats at the Staples Center in L.A., we're close enough to hear basketball players swearing. In the last few minutes of a belligerent game, full of glaring, taunting, and pushing, the hometown Clippers are in the process of erasing Dallas' comfortable lead, scoring 23 of the last 27 points. To Simmons' dismay, the crowd doesn't seem to appreciate that they're watching one of the best games of the year.

Clippers forward Blake Griffin, who has been the main target of Dallas' animosity, rises above the rim like he's wearing a jet pack and tomahawks a ball into the net.  The L.A. fans celebrate his feat with a mild golf clap. "He could dunk with his dick and nobody here would stand up to applaud," Simmons mutters. Unfortunately, we don't get to find out.

Yup, These Are His Leaders: Bill Simmons' Best Columns

Simmons was raised mostly in Boston, where every loss is like a death in the family, and even at 44, he watches sports with the delight of a kid — albeit a kid who's a multimedia mogul. During the NBA playoffs, which last nearly two months and end in June, he'll be a fixture on ESPN and ABC, via NBA Countdown. His 700-page Book of Basketball, despite being fatter than Eddy Curry in the off-season, debuted at Number One on The New York Times' nonfiction bestseller list. He goaded ESPN into making documentaries, which yielded 30 for 30, an excellent, Emmy-nominated series he executive-produces. His lively B.S. Report podcast, where he interviews jocks, actors, comedians college buddies, his dad, and Barack Obama, was downloaded 32 million times last year, and to keep him from bolting in 2011, ESPN gave him his own well-staffed website, Grantland. TV, books, documentaries, digital — it's the sportswriter version of the EGOT.

"We have similarly thorough backgrounds when it comes to movies, TV, sports and other worthless things," says his friend Jimmy Kimmel, who hired Simmons as a joke writer on Jimmy Kimmel Live! "Bill's very funny, he's married pop culture and sports more than anyone else, and he built his own media empire from a little blog."

That's not just tickle-tickle buddy talk. Simmons started to accrue a huge following in 1997, when he began blogging on AOL's Boston website in the role of an irritant and smart aleck, under the name Boston Sports Guy. Last summer, a Canadian columnist called him "an honest-to-God magnate" and "one of the defining figures" in digital media. All magnates have haters; Simmons makes it easy by frequently getting into feuds.

On NBA Countdown, Simmons plays a slightly exaggerated version of himself: a comedic troublemaker, "the wild card who doesn't give a shit," he tells me. "I'm part historian, part know-it-all, and part shit-stirrer. I don't hold back – that's the key."

During a recent Countdown, he denounced Brooklyn Nets shooting guard Joe Johnson, whom Simmons has tagged as the most overpaid player in the NBA. "Joe Johnson did not deserve to be on the all-star team," he says, so outraged and high-pitched he's nearly yelping. "Even he had to be shocked he made it." After the show goes off the air, Countdown host Sage Steele turns to him, shaking her head. "You," she tells him, "are a psycho."

The shit has been successfully stirred: Within minutes, Twitter is in flames. "Never hated a sports analyst as much as I hate Bill Simmons," I read as I scroll through his mentions, followed by "I want to punch him in the face," "He is such a douche" and "If Bill Simmons ever got in a car accident, I would be happy." There are compliments, too, but, let's face it, those are boring.

Simmons has 2.6 million followers on Twitter. Many can't wait to tell him what an idiot he is. (The Simmons brand has a strong ripple effect: Even his wife, known as the Sports Gal, has 25,000 followers, despite not having tweeted in almost a year.) Sports Twitter is a mire of stupidity, homophobia, and violent threats. It's probably the most inane culture on Twitter; at least on Politics Twitter, you occasionally come across a fact.

Simmons uses Twitter almost exclusively to promote and link to Grantland material. He doesn't reply to people who think he's a douche, or want to punch his face. He also writes fewer sports columns than he used to, partly because TV and movies occupy more of his time. The Internet gave him a career, an audience, wealth, influence, and fourth-row seats for the Clippers. But lately, Bill Simmons is kind of over the Internet.

Bill Simmons' Top 10 Go-To Writing Moves

On a Friday in January, Simmons and his Grantland staff scheduled a celebration: drinks at a glamorous hotel, after work, to celebrate the site's redesign. He and I talked for three hours in his undecorated office at ESPN's downtown L.A. complex, and a few times, he described his ambivalence about the effects of online culture.

Before the site launched, he decided Grantland wouldn't run slideshows, which draw big traffic but are dumb, or print reader comments, which breed idiocy. "Everybody was saying, 'Articles have to be short, because people have short attention spans.' And I felt like the opposite was true."

He built Grantland around long-form articles, the opposite of Twitter's enforced brevity, and hired writers known for their cleverness and insight, particularly with sophisticated sports statistics, rather than their snark: Jonah Keri for baseball, Bill Barnwell for football, Katie Baker for hockey, and for basketball, Zach Lowe, whom Simmons poached from Sports Illustrated by relentlessly pursuing him.

Unlike almost every other site, Grantland doesn't pick fights. "There's a mean-spiritedness on the Internet that we've stayed away from," Simmons told me in his office. "It seems to be getting angrier — especially Twitter, which is full of coyotes, waiting to attack the next victim." One false move, he added, and you find yourself in "a 24-hour shitstorm."

His thoughts about vengefulness took on a different meaning only a few hours later, when the shit-stirrer was now in a shitstorm of his own. Two days earlier, the site had published a story, "Dr. V's Magical Putter," about Dr. Essay Anne Vanderbilt, a female physicist who had invented a new, possibly superior golf putter. When writer Caleb Hannan investigated her background, he learned Vanderbilt was a transgender woman. Despite having agreed to her demand that he not write about her life, Hannan told Vanderbilt that he'd discovered the secret she clearly wanted to keep private, and he outed her to an investor. In the third-to-last paragraph of the story, Hannan revealed that Vanderbilt had committed suicide. It was a fascinating story, but also cruel and irresponsible.

Bill Simmons coaching in the NBA All-Star Celebrity Game in February.
Joe Murphy/NBAE via Getty Images

The initial reaction was favorable: other writers called it "a great read," and "mesmerizing," as they shared the link on Twitter. Richard Deitsch, a reporter at Sports Illustrated, said Hannan's article "might be the best I've read this month," an opinion he regretted four days later, after the article had been widely condemned. 

Unlike the controversy over Joe Johnson, there were genuine stakes in play. A political reporter called the "Dr. V" piece "absolutely, stunningly unforgivable." One Tweeter called Hannan "a fucking shit head and a murderer," and another said to him, "you harassed a trans woman until she killed herself."

On that Friday night, Simmons dismissed the furor — just more "mean-spiritedness on the Internet." Oddly, a master of new media was badly misreading what was happening. The next day, he took his daughter to her soccer tournament, and during a break between games, looked online, where the angry reactions had continued. "That's when everything turned," he says, "and I started to think we'd made a serious mistake. It snowballed over the weekend, and I started going into deep self-hatred."

The story's misjudgment was not the result of malice. The Grantland staff is more diverse, in gender and race, than most publications ("God forbid we ever get credit for that," he grumbles), and when I talked to him in the thick of the anti-Grantland tempest, he was clearly morose and regretful. "People hate our site now," he said.

But Simmons also didn't fully understand why people despised the article. "Crazy" and "hysterical" responses on Twitter had made him "embarrassed for mankind," and he didn't agree with me that Grantland never should have mentioned the fact that Vanderbilt was a transgender woman. Like a lot of people, especially people in the sports world, he's amiss in issues of gender and sexuality; a few weeks later, during a podcast in which he discussed Michael Sam, a college football player who came out in February, Simmons used the offensive phrase "sexual preference" – not out of hostility towards Sam, but out of ignorance. 

Simmons wrote a lengthy apology for the "Dr. V" story, which Grantland posted the next Monday. The article, he admitted, lacked empathy for Vanderbilt, and should not have outed her posthumously. His apology was thorough and almost self-flagellating, but was also mitigated by his defensiveness, which ESPN Executive Vice President and Executive Editor John A. Walsh told me he found "unfortunate." In addition, Grantland published a stinging critique by ESPN baseball reporter Christina Kahrl, who is a transgender woman; she denounced the story's ignorance and "casual cruelty." "By any professional or ethical standard," she also wrote, Vanderbilt's past "wasn’t merely irrelevant to the story, it wasn't [Grantland's] information to share."

And ESPN ombudsman Robert Lipsyte, an accomplished 76-year old writer, added his own column, in which he called the article "inexcusable" in its "unawareness and arrogance." He described Simmons as "a talented, overextended 44 year old" with "considerable vision and celebrity." Lipsyte did not intend "celebrity" as a compliment.

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