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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.

by russell scott smith
Write of Passage: The Sports Guy
Photography by: Steven Barry

Bill Simmons watched the fifth game of last October’s American League Championship Series in his Southern California home. For the first seven innings, it wasn’t very fun. The Boston Red Sox were losing to the Tampa Bay Devil Rays. His favorite team’s season hung in the balance, but they were down by seven runs and looked half-asleep on the field.

“I was getting ready to call my dad,” recalls Simmons. “It was time for a postmortem on the Red Sox season.”

In the meantime, Simmons tapped at the laptop on his knee, reworking a column about football set to appear on the next day. That’s what Simmons does for a living. The Greenwich Country Day and Brunswick School grad is famous across the country as ESPN’s “Sports Guy,” one of the best-known sportswriters on the Internet. He was an early pioneer of sports blogging, and his columns still draw some 500,000 unique visitors each month.



Nothing fires Simmons up like an exciting game, something that reignites the thrill he first felt watching the Celtics from front row seats as a kid in Boston.


But that night’s game wasn’t doing it — until the seventh inning. “Suddenly, my team woke up,” Simmons recalls. With two outs in the seventh inning, David Ortiz, Boston’s star designated hitter, crushed a fastball into the stands. Right fielder J.D. Drew followed with another home run. “I couldn’t move,” Simmons recalls. “I didn’t want to uncross my feet.”

It was 7-7 in the ninth when Drew came back to the plate. He knocked a single over the right fielder’s head. First baseman Kevin Youkilis danced home from third, and Fenway Park reached the decibel levels of a jet engine at takeoff. Final score: 8-7.

Some three thousand miles away, Simmons leapt from his couch, just as the phone started to ring. It was his father, from his home in Massachusetts.  “J.D. Drew!” Bill Sr. screamed. “I always liked him!”

“I know!” Simmons yelled back.

Another call came in. Then another. Simmons’s buddies were calling from around the country. His old friend Bug phoned in. A reader and Devil Rays fan named Darren e-mailed. This was big. Clearly, Simmons had a job to do. It was almost midnight, and that football story was in the can, but no matter. He wasn’t about to go to bed. With regret, he told friends that he had to get off the phone. “It was time to go into column mode,” he says.

Seven years ago, when Simmons first started at ESPN, he could have easily stayed up until dawn working on a column. That’s what he did when the New England Patriots knocked off the St. Louis Rams in the 2002 Super Bowl in New Orleans,  “After the game,” he recalls, “I drank about four hurricanes on Bourbon Street, then went back to the hotel room, finished the column at five in the morning and sent it to my editor. It was on the website a couple of hours later. I woke up at noon and was like, ‘Oh, my God, what did I do?’ ”

Simmons has mellowed since then. He met his wife Kari, whom he is fiercely protective of privacy-wise. Today they have two children, three-year-old Zoe and one-year-old Benjamin Oakley Simmons — whose middle name is an homage to former NBA power forward Charles Oakley and whose initials spell a not-so-subtle tribute to his dad’s favorite teams, the Red Sox, the Celtics, the Patriots and the Bruins.

“I’m on kid time now,” Simmons says. “My brain doesn’t work right past 2 a.m.” Yet he finished his column the night of the Red Sox win, fueled by exhilaration of the victory. The next day, his 3,300-word column appeared on the ESPN website, and it was vintage Sports Guy, definitely not a dry news-paper sports story. There were no predictable quotes about a team effort. Instead, Simmons did what he’s famous for, riffing on the game, the players, the fans and seemingly anything else that popped into his fertile mind.

One moment, he was discussing J.D. Drew’s $14 million-a-year salary — “a downright bargain” — and the next he was laughing about the play-by-play announcer’s weird pronunciation of “David ORRR-tese.” He lamented the shallowness of the nouveau Red Sox fan and poked fun at his dad, who almost gave up on the game after the sixth inning because he didn’t want to miss Maura Tierney’s final episode of E.R. When the Red Sox started scoring, Simmons called Bill Sr. to make sure he was tuned into sports — not medical — drama. The column’s last line was a pretty good summary of the Simmons philosophy: “You either love sports or you don’t.” For Simmons, the answer is an emphatic yes. His columns are full of a fan’s passion. They read like a late-night bull session with your best buddy, who also happens to be really funny and an encyclopedia of sports knowledge. They’re infectious and are available not only on his popular blog, “Sports Guy’s World,” but also in ESPN: The Magazine. His chronicle of the Red Sox’s 2004 championship season, Now I Can Die in Peace, reached number 19 on the New York Times best-seller list.

“How cool is my job?” he asks. “Something amazing like that Red Sox game happens, and I get to write about it. My story leads the next day, and a million people read it. Of course that gets me excited.”

Birth of a Sports Guy

“I have pictures with Bill at eight months old in a Red Sox cap,” says his mom, Jan Corbo. “He practically came out of the womb this way.”    

Simmons spent his first several years living in Boston, and by first grade, he was reading box scores for the Red Sox, the Celtics, the Patriots and the Bruins every day. One time, his father got a call from the principal. “They were upset,” Bill Sr. says, “because he wouldn’t start his school work until he’d finished reading the Boston Globe sports page.” A couple of years later, another call came from the school: “He was refusing to sign his name as William Simmons. He wanted everyone to call him Abdul-Jabbar Simmons.” Bill Sr., a former biology teacher who went on to become a middle-school principal and the superintendent of schools in Easton, Massachusetts, was the one who introduced his son to sports. Simmons is an only child and when he was six, his dad bought a season ticket to the Boston Celtics, near the tunnel where the players would enter from the locker room. The NBA was a lot looser in those days, and the ushers used to let Bill Sr. bring his small son into “the Gahden” for free.

Simmons sat on his dad’s lap, right next to the Boston Garden’s famous parquet floor, for every game of the 1976 season, as John Havlicek and Dave Cowens led the Celtics to a championship. Simmons was courtside for that year’s finals versus the Phoenix Suns, including the unprecedented three-overtime Game 5, often called the greatest game in NBA history. (Actually, the young Simmons slept through most of that one, a fact that his dad still ribs him about.) He was even allowed out on the court before games, and he got to rebound for the Celtics during their warm-ups. One night, a photographer from the Globe shot a picture of him, standing under the basket and watching the players intently. It wound up on the cover of the paper’s sports section.

“We sat right by the tunnel where the players entered and left the court,” Simmons recalls. “Over the years, I saw Bird up close hundreds of times. Michael Jordan walked right by me.” Their seats were so close to the action that Simmons and his dad often showed up on TV. And many of these old Celtics games are famous, so they run in regular rotation on the ESPN Classic nostalgia channel. “I’m always turning on the TV and seeing myself,” he says. “Those games are a record of my life. You can see me at different stages of puberty, from when I was six until the end of Bird’s career, when I’m there with my college girlfriend. In one game from the ’80s, my dad has this crazy Village People mustache. I still tease him mercilessly about that.”


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

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 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.”