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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.

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.