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.

Photography by: Steven Barry

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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 ESPN.com 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 ESPN.com 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.”


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