Write of Passage: The Sports Guy

Popular ESPN columnist and best-selling author Bill Simmons spent his most influential years in Greenwich playing hoops, making great friends, and cultivating his writing skills. Here, he shares how his hometown roots paved his path to sports media glory.



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When Simmons was in eighth grade, his parents got divorced and he moved from Boston to Stamford with his mother, who has worked at the Greenwich Avenue Lux, Bond and Green for many years. Simmons started at Country Day in the ninth grade, and most of his fellow students had known each other since kindergarten. “It’s not easy coming into a situation like that,” recalls Simmons’s basketball coach and English teacher, Wally Ramsey. “Bill handled it perfectly. He just came to our first practice and said, ‘OK, everybody, your point guard is here!’ He could say things like that and people didn’t take offense. Everyone just liked him.” That same year, Simmons wrote a paper in English class that was so good it stunned Mr. Ramsey. “When you’re a famous sportswriter,” the teacher wrote at the top, “I want to be your agent and get 10 percent.”

Wally’s son, Gus Ramsey, was two years older than Simmons, but the two immediately bonded. They were best friends throughout their teenage years, while they worked their way through Country Day and Brunswick. At one point, the boys started a 20-watt pirate radio station in a Greenwich Country Day classroom, playing records and making Howard Stern–style prank calls to their friends. Another time, they played ball in the Ramsey backyard with Mets hall-of-famer Tom Seaver, who was a friend of the family. And they spent hours in front of computer games on the Commodore 64 in Simmons’s basement, dedicating one whole summer to playing a complete 162-game season of the early sports-strategy game Micro League Baseball.

They also sparred jokingly over their different tastes in teams. “I was a Mets fan,” Gus recalls. That led to difficulties during the ’86 World Series, when the Red Sox of Jim Rice and Wade Boggs lost to Darryl Strawberry and Dwight Gooden’s Mets. “I don’t know how we survived that,” Gus recalls.

Perhaps even tougher was the rivalry between Celtics superstar Larry Bird and Gus’s favorite player of the era, Julius “Dr. J” Erving. “Simmons always called Larry Bird ‘The Basketball Jesus.’ He was obsessed with Bird; he even mimicked Bird’s pigeon-toed walk,” Gus recalls. “At one point, Dr. J and Bird got in a fight during the game. One of them got the other in a headlock. That was tough for me and Simmons. It nearly drove us apart.”

Actually, nothing could separate these two pals, and the five other buddies Simmons has from Country Day and Brunswick. They talk and e-mail almost daily and meet up in Las Vegas at least one weekend per year. “We stay in a casino, play blackjack until obscene hours, and make fun of each other,” Simmons says. “It’s like time hasn’t passed at all. We fall back into all the same jokes.” These lasting Greenwich friendships have been especially important to Simmons, since he doesn’t have any brothers or sisters. “Those two schools were the best things that ever happened to me,” he says.

Simmons often thinks about returning to Greenwich so his kids could have a similar experience. “I look at my daughter, and I think about the way fifteen-year-olds dress in Los Angeles,” he says. “I don’t like the winters in Connecticut, but I’d like my kids to go to Country Day. It’s such a special place, full of kids who were raised well. It had a big impact on me, and it would be the number one reason I’d come back.”

Making It Big

After majoring in political science at Holy Cross (and writing a sports column for the newspaper that planted the seeds for his successful style), Simmons studied journalism at Boston University, and then took an entry-level job at the Boston Herald, covering high school games. But he chafed at the stiff conventions of newspaper writing and soon found another outlet, writing columns on Boston’s Digital City website while working as a bartender to supplement his bare-minimum wage.

At first, Simmons called himself “The Boston Sports Guy,” but his column quickly built up a national following, partly because he had so many friends from high school and college, and they all e-mailed it to each other. Gus Ramsey had taken a job as a producer at ESPN’s Sports Center, and he passed his friend’s columns to Keith Olbermann, Dan Patrick and other folks in the network’s Bristol, Connecticut, headquarters. In 2001, Simmons moved his column to ESPN.com.

Simmons writes like he’s talking with friends, and he has made many real-life buddies through his column. Kindred spirits from around the country often e-mail him, and sometimes that turns into long-lasting back-and-forth conversations. Simmons got to meet the late Hunter S. Thompson that way, and the original gonzo reporter has clearly influenced Simmons’s own technique. Jimmy Kimmel is another longtime Simmons reader who eventually became a pal. In 2002, Kimmel invited Simmons to move to L.A. to write for his late-night talk show. The job lasted only about a year and a half, but Simmons stayed in California.

Kimmel jokes that his friend wanted to go back to watching TV for a living, but in fact Simmons has kept busy. His ESPN.com columns are still popular, and he’s mastering a new medium with his ESPN podcast, The BS Report, regularly the most downloaded audio on the site. Simmons is also breaking into television production for ESPN. He came up with the idea that became 30 for 30, a series of documentaries about the last three decades of sports that will air this fall as part of ESPN’s thirtieth anniversary celebration. Simmons is an executive producer on the project. He hired some top Hollywood names to direct the documentaries, including Spike Jonze (Being John Malkovich) on BMX biking star Mat Hoffman; Barry Levinson (Rain Man) on the Colts leaving Baltimore; and Ron Shelton (Bull Durham) on Michael Jordan’s brief pro-baseball career.

But even as Simmons has branched into other media, writing remains his passion. “I really like writing books,” he says. Now he has a new one, The Book of Basketball: The NBA According to The Sports Guy, which hits stores in October. It’s a collection of Simmons’s thoughts on nearly the whole history of pro hoops, including his ranking of the top players in NBA history. He won’t say who’s on the list, but promises that some of his choices will surprise. “I spent a lot of time trying to figure out which guys mattered,” he says, “and whether there’s a common theme that makes the great players great.”

The book also revisits subjects that led to some of Simmons’s most intense columns, such as the tragic 1986 death of University of Maryland All-American Len Bias, just forty-eight hours after he was drafted in the first round by the Celtics. It also includes a blow-by-blow account of his infamous feud with former Knicks general manager Isaiah Thomas, who threatened to punch Simmons during a 2006 interview because he was mad about one of the Sports Guy’s columns. The two eventually met to discuss their differences, but Simmons refuses to discuss what happened — at least for the moment. “I don’t want to spoil the surprise,” he says. “You’ll have to read the book.”

One of the book’s footnotes lists twenty titles that Simmons wanted to use before his publisher nixed them. There’s Tuesdays with Horry, a joking tribute to Mitch Albom’s bestselling book Tuesdays with Morrie and longtime Los Angeles Lakers power forward Robert Horry. Then there’s Tell Me How My Book Tastes, which riffs on a profane insult that Shaquille O’Neal threw at Kobe Bryant last summer, during a freestyle rap onstage at a New York City nightclub. Simmons also had to give up on his original idea, The Best Basketball Book Ever Written. That title was meant as a joke, of course. But it reveals something about Simmons’s ambitions for the rest of his career. “I really wanted to write a great book,” he says. Internet columns won’t cut it forever. “I want to do something special, something that will last.”   

 

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