Bill Simmons Shoots, He Scores

One of the Internet’s first success stories, the ESPN columnist writes about sports like he’s living in the cheap seats

For his ESPN column, in podcasts, and on the cover of his new 700-page epic, The Book of Basketball (Ballantine/ESPN, $30), Bill Simmons styles himself “The Sports Guy,” but that’s an inadequate title. This summer, weighing in on baseball’s steroid mess, he evoked Koufax and Mantle but also Melissa Rivers’s fragile emotional state, the Good Ship Lollipop, and the U.S. Constitution. A product of Connecticut prep schools, Simmons came to L.A. to write for Jimmy Kimmel Live. Though he’s moved on, he still shares Kimmel’s delight in professional sports and its relation to the absurd. Such eccentricities have only helped make the 40-year-old Simmons the most entertaining horse in ESPN’s stable. We spoke with Simmons about being a Red Sox fan in Dodger Blue country, the Clippers’ ignominy, and the brilliance of one Kobe Bean Bryant.

How was “The Sports Guy” born?
In the  mid-1990s, I worked at the Boston Herald for three years as a sports reporter. I hated it there. It was a miserable place, and I finally quit. I bartended for a year and thought, this might be it. Around that time AOL had this thing called “Digital City.” It was ahead of its time because its goal was to be an electronic newspaper. I talked them into giving me a site called “The Sports Guy.” I was getting, like, $50 a column.

When did you realize the Internet was the next big thing?
It was November of 1997, when the Red Sox traded for [pitcher] Pedro Martinez. That happened in the morning. My column went online at, like, 1:30 in the afternoon, and I got all this reaction. People were e-mailing me and forwarding it to their friends. Meanwhile the newspapers weren’t coming out for another 16 to 18 hours. I started thinking, this might take off. By the time anyone reads the newspaper, they’ll have read my column a full day before.

You write your column without venturing into the press box or the locker room.
When  I was in Boston, I’d call up the Red Sox and ask for a press pass. They’d say, “Who do you write for?” I’d say, “Digital City.” They’d say, “No.” Eventually I settled into writing from the fans’ perspective, about fantasy sports, Las Vegas, and betting-guy stuff. I knew it was going to work because it was so different from everybody else. The rest of sports media was entrenched, middle-aged white guys. They didn’t seem like they even liked sports.

Your first book, Now I Can Die in Peace, was about the Red Sox. Now you’ve written 700 pages—with footnotes—about the NBA.
I wanted  to write a great basketball book. The initial goal was to figure out the top 90 or so players in basketball history and then rank them in order—like a Hall of Fame pyramid. I’m fascinated by the whole concept of why certain players matter more than others, why some guys endure and others don’t. I think that’s universal: Why do De Niro and Pacino matter, but Harrison Ford never gets brought up even though he’s arguably had a better career? But I don’t think people should be intimidated by the page length. It’s the type of book you can pick up, put down, skim ahead, consume however you want. By the time you’re done, you’ll feel like you understand the NBA.

You’ve long rooted against the Lakers, in particular Kareem Abdul-Jabbar. Yet you rank him as one of the greatest players of all time.
Kareem was my least favorite player growing up. He was an aloof, unfriendly guy with the skyhook, the most amazingly effective shot we ever saw. But also pretty boring. Robotic: the same shot every time. When you look at what happened to the league in the 1970s, he gets some of the blame. He was the signature guy, but fans couldn’t connect with him in any way. Jim Murray interviewed his back once. How bad of a personality do you have to have that Jim Murray said, “I’m going to interview this guy’s back”? But it was important for me to have the rankings right and to feel that there’s no bias. I have Kareem and Magic ahead of Bird, which just murdered me. It tore my heart out and stomped on it, but there was no other way.

Your feelings about Kobe Bryant, whom you have tied with Jerry West for the number two spot on the Laker greats list, have changed.
I don’t think I’ve ever written about any athlete more than Kobe. He’s polarizing. He’s changed the most over the years, and he’s unique because he’s actually succeeded as an individual in a team sport, which has only happened twice. It’s him and Wilt Chamberlain. They’re the only guys who are great enough to supersede the team, turn everyone into their cohorts, but still win. I respect Kobe. Look what he’s done the last two years: two NBA finals, one title, the Olympics, and he played 218 games in two years. Would I want to play with him? No. Do I think he’s a genuine person? I really don’t. I think he puts too much thought into how he’s perceived.

The Lakers signed Ron Artest to replace Trevor Ariza. You wrote that “this won’t end well.”
The Lakers have violated one of the rules for putting together a [championship] team: They’ve chosen to add Artest, who is only the most completely insane person we’ve ever had in the league. Meanwhile Lamar Odom signed a big contract and has married a Kardashian [Khloe]. Now, I wouldn’t count out the Lakers. We’re going to know when we see Kobe in training camp what kind of shape he’s in. He might decide, “I want to win two and I’m gonna kill myself to do it.” If he’s properly motivated, I wouldn’t bet against him. But I’m thinking it’s going to be San Antonio.

As a Clippers season-ticket holder, you’ve ripped coach-general manager Mike Dunleavy. Do you think Dunleavy the general manager should fire Dunleavy the coach?
I think they should fire each other. He’s the first coach ever to coach 300 games for two different teams and have a sub-.400 winning percentage for both. He’s made history. It’s an organization that’s so fucked up that it’s perfect for him.

You talk a lot about race in the book.
Race permeates every part of the NBA. It’s the single most important issue with the league. Everybody thinks baseball is the sport that reflects American society with race. I would say it’s basketball. There are no black guys left playing baseball. But in the NBA, a guy like Allen Iverson is hugely important in the inner city because of the cornrows, the tattoos, his attitude.

What surprised you in researching the book?
All the drugs in the 1970s and what a huge problem they were. It was more than an epidemic, it was almost a catastrophe. It took them a whole decade to get rid of it.

You include a ton of footnotes.
I’d never seen anybody do that until I read David Foster Wallace. He wrote this article about [tennis player] Michael Joyce that was in a Best American Sports Writing anthology. I thought the footnote was such a weird gimmick, but it’s so liberating for me. I feel like it’s the right format for my style. It makes me mad that footnotes don’t work on the Internet. I have to use parentheses instead.

Malcolm Gladwell, Chuck Klosterman, and William Goldman contributed to the book. Who knows the most about basketball?
Goldman, because he’s been going to Knicks games since the ’60s. He’s watched the league evolve. The book he wrote with Mike Lupica, Wait ’Til Next Year, had a huge impact on me. It was such a neat idea for a book. It shaped how I write my columns.

How do you survive as a Boston fanatic who lives in L.A.?
It’s not as hard as I thought it was going to be because there are so many transplants here. I have a lot of Boston friends. Also, there’s Direct TV. I think if I’d come here earlier, I would’ve been miserable because I wouldn’t have been able to watch my teams. But now it doesn’t really matter where you live ’cause you can watch every game. I do miss going to Fenway. I do miss going to Celtics play-off games. But the trade-off is 80 degrees every day.

Do L.A. fans get a bad rap?
A team like the Dodgers , which I’ve come to appreciate, has real fans, real history. Dodger Stadium is arguably the greatest stadium in the country. It’s between Fenway and Dodger Stadium. You go to a game at Dodger Stadium, and Ron Cey or Tommy Davis will be on the infield before the game. It’s cool.

How about Laker supporters?
It’s funny how the Laker flags on the cars come out in June. Where are they in December? To have Laker tickets, you have to have money. It’s, “Yeah, I got tickets from my agent.” Or, “Yeah, my buddy’s rich, and his dad gave him tickets.” The best crowds are for the bad games. If you go see them play Memphis, it’s all real fans because it’s their one chance a year to go.

Manny Ramirez left the Red Sox for the Dodgers.
I’m glad he was in Boston, glad we won two titles with him. But his personality is perfect for here. He’s bilingual, happy-go-lucky—he sort of fits in.

Your take on his being suspended for steroids?
It definitely tainted my baseball fanhood. It’s pushed me a little toward basketball and football. At least in football, I know the guys are cheating. It’s funny that this is the one city where he could have gotten away with what happened. This is a city where people are so used to breast implants and Botox and all kinds of stuff, nobody here really reacted to Manny. With the suspension, they were, 50 games, he’ll be back; it’s all good. They didn’t even take down the Mannywood billboard on Sunset.

How’s ESPN as a boss?
They’re the mothership I needed to get to. Creatively, they play it safe a lot. They have to because they’re a very complicated company that has a lot of different goals and makes a lot of money. I do think they underestimate the general public sometimes. I almost quit doing my podcasts because they were taking out stuff and bleeping stuff. I was, like, give me some leeway with this. It took a while, but to their credit, they did.

This fall’s “30 for 30” documentary series—30 films for ESPN’s 30th anniversary—is ambitious, ranging in topics from O.J. to BMX to the Raiders’ L.A. era. How did you become a producer on that?
I sent ESPN a memo about how it bothered me that HBO had become the go-to network for sports documentaries. We’re ESPN, we should own that. The problem was, ESPN had kind of burned its bridges with Hollywood. But once we started brainstorming ideas and getting commitments from the directors—once we got Barry Levinson in, once we got Ron Shelton in—it was like dominoes. We’ve assembled a dream team of directors: Brett Morgen, Ice Cube, Spike Jonze, Peter Berg, and on and on.

What’s next?
I’m definitely going to try something big. I just don’t know what. I’m ready to go down in flames on something so that people say, “Did you hear about Simmons? He lost $20 million in two months. All the investors want to kill him.” That’s one of my goals.