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Bill Simmons' Big Score

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In his columns, Simmons embodies the precise average of American maleness: He loves sports, movies, fantasy baseball and hot actresses, and is not unfamiliar with porn. "I don't have a shitload of hobbies," he says. "I'm not very complicated."

Once a year, he goes to Vegas with several friends — to gamble. "He's much more interested in playing cards than in seeing naked girls," Jimmy Kimmel says, with a tone of disdain. On his podcast, Simmons often talks about betting on games — up to $1,000 on individual games, or $2,000 on futures bets, he tells me. "I love gambling. I wish it was legal. But I never bet a lot, even in Vegas. Unless I'm really drunk."

He won't say whether or not he has a bookie in L.A., which means he likely does. And if he offers you a bet, you should probably take it — last football season, he won only 108 out of 256 picks against the spread in his column. "It was kind of a bummer," he says, though he points out that in 2006, he had his wife Kari make her own football picks in his column. "And she beat me. So if I had credibility after that gimmick, it was an accident." (Kari was also at least as funny as her husband. She said Lindsay Lohan would "look like a leather purse in 25 years no matter how much Proactiv she takes," and theorized that Katie Holmes "had her ankles removed" so she'd be the same height at Tom Cruise.)

Simmons will always be associated with New England — he might love Tom Brady and Larry Bird as much as he loves his wife and two kids — but he's unsentimental about his roots. "I don't think you could get him to go back to Boston at gunpoint," Kimmel says. Simmons is credited as an Internet visionary, but he went into new media only because old media rejected him. "Boston," he says, "is where I failed."

He began his career as a lackey at the Boston Herald, the lesser of the city's two daily papers, "organizing Chinese-food orders" and covering high school teams. He stood outside the Herald building on the Mass Turnpike, smoking cigarettes and "wondering what the fuck I was gonna do with my life."

Except for the addition of tall buildings, Boston hasn't changed since Paul Revere bought a horse. TV anchors and newspaper columnists keep their jobs for decades, and at the Herald, "mediocre writers were blocking my way," Simmons later wrote. 

Simmons interviews the president for his podcast.
Courtesy of "B.S. Report"

"I didn't do myself any favors," he adds now. "I was probably too arrogant, and could barely hide my disdain for some of the writers." After three years, "frustrated to the point of insanity," he quit and worked as a bartender. At 24, he began smoking pot, and soon owned a four-foot purple bong. (In L.A., he discovered West Coast weed was way more potent, and one night, ended up "hiding behind the curtains in my living room for 40 minutes because I thought somebody was watching us. After that, I phased back big time.") He considered going into commercial real estate with his stepdad before he came across a new website, AOL, where even a Herald reject could write.

He wrote with a fan's dismay and delight, rejecting the idea of being objective (a Boston partisan, he openly despises the L.A. Lakers and any team from New York), and attacking local sportswriters by name. No team would give him a press pass, so while newspaper guys padded short articles with boring quotes from athletes, Simmons distinguished himself by mixing in references to bands and movies (especially Shawshank Redemption and Karate Kid), and by writing long: "85,000-word essays about Rocky IV," Kimmel jokes.

Simmons' early work had flaws — bitterness, cheap cracks about the manliness of female athletes, praise for the Counting Crows — but it was also funny, fresh, expansive, and even sentimental, especially when he wrote adoringly about his dad and their sports bond. That's the secret element of Simmons' success: He's the most emo sportswriter around. He once penned a 3,000-word column describing how his dog Daisy died of lymphoma. It's the Fall Out Boy of sports columns.

In 2000, when ESPN launched Page 2, a site that mixed sports, pop culture and humor, Simmons waited for his phone to ring. "That was probably the lowest I sunk, when ESPN didn't hire me for Page 2," he says. He was in his early thirties, still borrowing money from his parents. A few months after the launch, he wrote a column mocking ESPN's annual awards show, and his taunts got noticed. "I was on the floor laughing," recalls ESPN's John A. Walsh. Soon, Simmons had his first ESPN assignment. If there's a moral, it's this: Bite the hand you cannot kiss. 

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No sportswriter has ever had as much success as Simmons, partly because sports is now inseparable from pop culture. Even if you don't care about football, you know Peyton Manning from his ads for Buick. Or DirecTV. Or Gatorade. By integrating with television, digital media, and Madison Avenue, sports has shifted from a pastime to a conglomerate: according to Forbes, the four major professional leagues are worth a combined $91.2 billion. This makes it harder to care about sports — who roots for Comcast, or Chevron? — but the enthusiasm of Simmons' columns and podcasts return fans to the spirit of the pre-show-me-the-money era.

ESPN has both enabled this growth and benefitted from it, and is now worth $50.8 billion, making it the most valuable media brand in the world, according to Forbes, with 7 domestic and 24 international TV networks, radio networks, a weekly magazine and websites. That's a staggering sum for a network that launched in 1979 with a lineup of college soccer, wrestling, and slow-pitch softball.

Tony Kornheiser, a Pulitzer Prize finalist for his sportswriting, and a host of ESPN's lively Pardon the Interruption, calls this "a Golden Age for sportswriters," though not a Golden Age for sportswriting. In spite of all these opportunities — or maybe because of them — sportswriters have never seemed more unhappy. They bicker like Real World cast members, and beef like gangsta rappers in the Nineties. And Simmons is often in the middle of these tiffs, partly because people only beef up, and partly because Simmons' name guarantees website traffic, especially if he replies.

Deadspin is to mocking Simmons what Michael Jordan is to basketball, so I asked Tommy Craggs, the site's editor, to summarize the case against him. Craggs denounced Simmons' "chuckling, incurious, cleverest-guy-standing-around-the-Phi-Delt-keg writing voice," and dismissed him as "nothing more than a dispenser of dull, honkified conventional wisdom about sports." He also said Simmons had been smart in not hiring Bill-Jr. clones at Grantland, adding that a site full of Simmons-ish prose "would suck."

What is it with these guys? They're nearly as bad as Sports Twitter. Charles Pierce of Esquire wrote a snarlish review of Simmons' Book of Basketball (on Deadspin, of course), mocking his frequent digressions into gambling, movies, his friends, and strip clubs, and concluding with the words, "Get the fuck over yourself." This lead to an angry exchange of emails and posts, during which Pierce called Simmons a "mendacious, whiny little thin-skinned bag of breeze." Several months later, Simmons hired Pierce as a staff writer, so presumably, all has been forgiven. Also: Tommy Craggs, Simmons' chief tormenter, was set to take a job at Grantland in 2011, before he shit-talked an ESPN.com writer and the new job fell apart. Why do even Simmons' most severe critics want to work with him? 

For an impartial opinion, I asked a younger journalist who works for one of ESPN's competitors if he thought Simmons is a good writer. "As far as craft? No. His pieces are too long, there's too much I in them, and he goes on too many tangents. But he's very smart, he's wittier than all the people who imitate him, and he has an almost encyclopedic knowledge of the NBA. The Internet made Bill Simmons, and it also produced all the people who like to tear him down. That's the thing about the Internet — it makes its own gravy, over and over again."

Once Simmons got an ESPN assignment, he quickly found an audience. But just as immediately, his relationship with the Worldwide Leader in Sports was full of conflict. "ESPN was idiotic," says Simmons, who can match any athlete for self-confidence. "They fucked with my column for the first year, taking out jokes, and I was pissed off. They were rebuilding their site around me, but they were paying me nothing. So I had a meltdown: I didn't turn in a column. I was like, 'Attica! Attica!' " He laughs. "I was probably smoking too much pot." 

ESPN rewarded his work strike with a raise. "Bill likes to be in control," an insider says. "In the early days, he was very upset about where they placed his column, versus where other columnists were. He's a great advocate for himself and his brand."

It wasn't Simmons' last fight with his bosses. They've suspended him from Twitter twice for tweets: for referring to Boston sports-radio hosts who worked for an ESPN affiliate as "deceitful scumbags," and also for saying an interview that aired on ESPN was "awful and embarrassing." Does he think they were right to suspend him? "No, I don't."

ESPN is owned by the Walt Disney Company, and some of Simmons' behavior — like, say, calling soccer "gay" or mocking people for being fat — makes him a far more troublesome employee than Mickey Mouse. Periodically, the two parties get annoyed at one another. ESPN president John Skipper once said working with Simmons was "about 99.8 percent great." ("Working with ESPN is 99.1 percent great," Simmons counters.) Convincing the network to do 30 For 30 required "a year of arm-twisting," he says. When it was a success, and his basketball book had been a big hit, his contract was up for renewal. "I had a little leverage." He told ESPN that he wanted his own site, or he'd leave and do it elsewhere.

Grantland's success, like Simmons', has resulted from good fortune as well as talent. Since 2002, Boston teams have dominated pro sports, tallying eight titles in twelve calendar years, including baseball, basketball, hockey, and football. No other city has ever had that kind of success, and it brought a lot of attention to Simmons. No wonder he loves Tom Brady so much.

"When we were launching, we didn't realize technology advances would help us so much." GIFs, Instapaper, wi-fi, embeddable links — all foster the ease of promoting a digital magazine. "The iPad has been a godsend — it's probably the greatest thing that's' happened to Grantland. Nobody knew the fucking iPad was coming. I didn't. We hit at the right time."

In a recent month, Grantland, according to comScore, had 4.7 million unique visitors, which represents just a sliver of ESPN's 62 million unique visitors and pales compared to Yahoo Sports' 57.9 million. (Even Deadspin, the Johnny Lawrence to Simmons’ Daniel LaRusso, had 13.8 million.) But the site's balance sheet isn't the point. ESPN likely pays him more than $5 million a year, the insider estimates — not because of Grantland, but because Simmons is a guy with big ideas, a one-man vertical-integration engine.

Now that he oversees an empire, Simmons says he doesn't care as much about Boston teams. "It's not life-or-death anymore," he says with a shrug. But that might not be true. His daughter loves L.A.'s hockey team, the Kings, so he took her to see them play his team, the Bruins. "Boston won, and I taunted her on the way home. She started crying. She was, like, six years old." A few years later, they went to another Kings-Bruins game, and this time her team won. "She was yelling and high-fiving everyone," Simmons says, "and she taunted me." Of course she did. It's in the bloodline. 

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