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October 22. 2011 8:02PM

Kevin Gray's On Baseball: A lifetime of preparation for Ben Cherington


Ben Cherington is shown pitching for Lebanon during his high school days. 

From the bleachers of Fenway Park, Ben Cherington watched his first Red Sox game as a 5-year-old.

Little Ben, sitting next to his grandmother, Rita, who organized the trip, was captured by the game itself and never lost interest in the game, or whined for popcorn.

“Ben was just riveted,” his mother, Gretchen, said. “I think every other 5-year-old wasn't paying attention, but he just watched what was going on. There was a focus and passion for the game way back then.”

Cherington became a National Merit Scholar finalist and an excellent pitcher at Lebanon High School, carving through lineups by outsmarting the competition and making the most of his talent.

Now 20 years after pitching Lebanon to the 1991 Class I finals, the New Hampshire native will take a similar approach as general manager of the Boston Red Sox. The official appointment is expected Tuesday at Fenway Park.

When Theo Epstein showed interest in working for the Chicago Cubs, the Red Sox immediately turned to Cherington, a 37-year-old who's spent a career preparing for this moment. As team president Larry Lucchino once said, “When I think of New Hampshire, I think of Ben Cherington because of all he's done for this organization.”

Rising to the top

Cherington's road to Fenway Park's front office began in 1998, in Cleveland. The Indians hired Cherington as a video advance scout, acting on a recommendation of fellow Amherst College graduate Neal Huntington, also a graduate of Milford High School. Cherington worked 100-hour weeks, engrossed in a system that featured Huntington — a future Pirates GM — and other rising executives such as Josh Byrnes (currently GM of the Diamondbacks) and Paul DePodesta (Dodgers GM).

After a long season with the reigning American League Central champs, Cherington was hired by then-Red Sox GM Dan Duquette. By the time Cherington reached age 28, he'd already served as amateur scout, coordinator of international scouting and assistant director of player development. He was later promoted to director of player development, where he oversaw a farm system that helped produce World Series champions in 2004 and 2007.

“He's learned a number of different jobs to learn the business from the ground floor up,” said Duquette, who hired Cherington in 1999.

Cherington helped build a farm system that produced multi-year All-Stars Jonathan Papelbon, Dustin Pedroia and Kevin Youkilis, but he never overlooked the lower-profile minor leaguers — those who never made it.

Kyle Jackson of Litchfield, drafted in the 32nd round, beat the odds and earned a spot on Boston's 40-man roster before his eventual release. From the day he was drafted in 2001, Jackson knew only one constant in the Red Sox' front office: Cherington.

“He's seen it all. He has pretty much every idea of how to be a GM,” said Jackson, an Alvirne of Hudson graduate, who had elbow surgery to remove bone spurs last year. “I always found him to be very personable and easy to talk to. He never put anyone above. If you perform, you get moved up whether you're a first-rounder or a guy like me drafted in the 32nd round. In the end, they gave me every opportunity.”

Intelligence and vision

Former Lebanon High baseball coach Chuck Hunnewell, who always checked on his players' grades, knew Cherington had the intelligence and self-confidence to succeed.

“This wasn't any average intelligent kid,” said Hunnewell, who coached at Hanover and Lebanon for 36 years. “We're talking about a Merit Scholar and a kid that was motivated. The other thing was he never got rattled about anything. He wasn't a rah-rah guy. He was a quiet leader and led by the way he did things.”

Cherington grew up in Meriden, a small village of Plainfield, and was often surrounded by intellectuals and scholars. His grandfather, Paul Cherington, taught at Harvard Business School, and was an assistant secretary of Transportation in the Nixon administration. His grandfather on his mother's side, Richard Eberhart, won the 1966 Pulitzer Prize for poetry. His mother's cousin, the late Susan Butcher, became the second woman to win the Iditarod sled dog race, of which she was a four-time winner. She died from cancer in 2006 and is commemorated in Alaska on the first Saturday of every March, Susan Butcher Day.

“Ben followed her and was very close to her. She was inspiring to him,” Cherington's mother said. “He grew up around people on top of their field, in different fields. It's small town, maybe 700 residents back then, but he knew there were things one could do in life.”

As a junior baseball player at Amherst College, the right-hander suffered a shoulder injury and needed surgery. He became more of a player-assistant — and began setting his sights on a front-office career in baseball. Gretchen Cherington, on a car ride back then, remembers when that vision came into focus.

“He was a junior at Amherst. We were in the car, and I asked him what his life might look like down the road,” Gretchen said. “He said, ‘I want to help a team get to the World Series.' I was like, ‘Wow. Really?' I'd never heard him say that. He's very thoughtful when he speaks, and he really wanted to get a team to the World Series. So he did. Twice.”

Staff writer Kevin Gray covers pro baseball for the New Hampshire Union Leader and New Hampshire Sunday News. His email address is kgray@unionleader.com; blog: graymatter123.blogspot.com.


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