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Thursday, November 3, 2011
Updated: November 4, 9:04 AM ET
New GM Cherington swinging for fences

By Jackie MacMullan
ESPNBoston.com

During the long, lazy days of summer, young Ben Cherington assembled his trusted friends, grabbed his whiffle ball bat and assumed his stance, demonstrating an uncanny knack for recreating the batting tendencies of each of his beloved Boston Red Sox players.

When the bitter New England winters settled in with a sheet of snow and icicles hanging menacingly over the lip of the roof like winter fangs, Cherington remained undeterred. He moved his performances inside, mimicking the habits of his favorite hitters in the kitchen, by the fire.

Watch. Here's Jim Rice, throwing his hand aloft after he connects on a fastball, almost as though he's waving. Can you guess this one? It's Ellis Burks, the cerebral outfielder whom Cherington so fervently admired.

Jim Rice
Ben Cherington's passion for the Red Sox dates back to the heyday of Jim Rice, whose swing is imitated by the future GM.

Ben would leave friends and family choking with laughter over his impressions, his humor surpassed only by the adeptness with which the 10-year-old captured the nuances of the game that would consume his life.

During precious pilgrimages to Fenway with his grandmother Rita, he locked into the pitcher, mesmerized by the fluid throwing motion, by the power that seemed so effortless. He studied Baseball Digest from cover to cover, implored his parents to drive dozens of miles to secure a Sunday Boston Globe so he could devour the baseball notes column. He and his buddies collected baseball cards, but, explained lifelong friend Ben McGee, "The rest of us only cared if it was a rookie card. What interested Ben was all those numbers on the back."

"He memorized them all," concurred his mother, Gretchen. "Every statistic."

Years later, as he established himself as a new-wave baseball scout, Cherington was known to occasionally perform a rendition of Nomar Garciaparra at the plate, capturing his frenetic stance, including the trademark jittery back toe tap.

But by then Ben Cherington wasn't idolizing Nomar, he was analyzing him. And, in July 2004, he was part of a baseball operations team that shocked baseball by trading the popular shortstop.

"I thought it was a good idea," Cherington said. "I understood the very best Red Sox teams were able to play good defense, and we weren't doing that. And there was clearly something going on with Nomar. He wasn't as happy as he'd been in the past for whatever reason.

"It was a bold move by Theo [Epstein], to trade his franchise player.

"I've always felt it was the turning point. It wasn't just winning the World Series. It was winning it after trading Nomar. We reached a threshold I don't think we would have ever reached if just one or the other happened."

Ben Cherington
Cherington was all smiles on the day he ascended to the GM's office, but don't be fooled: He means business.

While Cherington values the data and "objective" side of the game, his "natural bias" toward the subjective components is perhaps one of the most telling differences between him and his predecessor.

Epstein lauded J.D. Drew, armed with statistical subtleties that he could recite from memory. Yet there was a disconnect with the right fielder that many fans could not reconcile. How any player could be utterly devoid of emotion as his teammate (Jacoby Ellsbury) stole home directly in front of him was mind boggling to many.

"Drew is an interesting case," Cherington said. "At his best he was a guy appreciated by both the objective and subjective camps. When he was at his best he had incredible physical skills that any scout could see. But if there was a failing, it was things like [the lack of emotion over the Ellsbury steal].

"I put a value on that. I prefer to have players for whom the game means something, as opposed to players who don't care so much about the game."

Making a stand for Crawford

The collapse of the 2011 Red Sox begs the question whether his current roster exhibited that required passion. Tales of cold brews and finger-lickin' chicken have shredded their credibility with the paying public.

"I don't believe I'm being stubborn about it, but I still believe we have a core of players who care about the game," Cherington said. "It's something we have to look at, but I really don't believe the end of the season is who we truly are."

That includes Carl Crawford, the gifted but underachieving outfielder. Cherington conceded at his introductory news conference that he not only approved of that lucrative free-agent signing, he advocated for it.

"During the last offseason we felt as an organization -- not just baseball ops -- that given what had happened the previous two years, and given that we had a little gap in the farm system at the very top, and what the threat of another disappointing season would have on the success of the business, we felt we needed to strike big," Cherington explained.

Adrian Gonzalez was the primary target, yet each time Crawford's name came up, Cherington lingered over his scouting report.

"We felt Crawford was a little underappreciated because he was helping teams win games in a slightly different way than highly paid players," Cherington said. "He wasn't hitting 40 home runs, but he was playing incredible defense, stealing bases and hitting 20 homers with a lot of doubles. We felt he was a top-five player in the league even though he didn't have Miguel Cabrera numbers.

"We thought he'd have a big impact on the game. He was a hard worker, well-liked in the clubhouse, and relatively young for a free agent.

"From a scouting perspective, he was an incredible athlete who got to the big leagues and was still learning how to play. We felt he was on an upward arc in terms of skill development -- or so we thought."

With Gonzalez already acquired and the winter meetings approaching, Cherington said Boston considered Carlos Beltran but Crawford approached the Red Sox, declaring, "This is where I want to be."

And that is when Cherington made his case.

"I told them, 'If we're going to do this, this is the winter to do it, and I believe this the guy we should do it with,'" Cherington revealed. "Theo bought into it, but I'm the one that pushed it.

"Then we had a conversation with ownership, and I had to push them too.

"I've learned a lot. One part of the puzzle is doing all the scouting, the background, the info gathering, the negotiating. But it can't stop there.

"You've got to keep going. It's a huge adjustment for these guys. We need to do a better job of getting to know Carl well enough to make him feel comfortable, because we've seen how good he is when he's comfortable.

"It's also on him to figure out ways he can make himself better acclimated next year."

Carl Crawford
Cherington pushed hard to convince Sox brass to sign Carl Crawford, and the new GM is hoping his left fielder gets more comfortable in 2012.

For a new GM to begin his tenure by accepting accountability for one of the team's most controversial moves is unorthodox, but, insist Cherington's lifelong friends, to be expected.

"Ben's always been accountable, as well as unflappable," said David Hall, who grew up with Cherington in tiny Meriden, N.H. "He's never been impressed with what he's accomplished."

Dreams dashed

The boys from Meriden grew up tight, fiercely loyal. They were spread about town, and, according to Cherington, "It wasn't riding your bike a couple of blocks. It was riding your bike a couple of miles. You kind of had to work to have fun. You had to earn it."

Each of Ben's birthdays was a new baseball adventure. One year they drove to Nashua to watch the Double-A Pirates, where a memorable brawl that included future major leaguers Bobby Bonilla and Paul O'Neill broke out.

Then there was the overnight trip to see the Montreal Expos. McGee was a catcher and a fervent Gary Carter fan, so it was a perfect baseball event -- until McGee realized halfway home he'd left his signature Carter catcher's mitt at the park. Fortunately for him, the Cheringtons understood a $14 glove lovingly broken in by a heartbroken kid was priceless, so they turned around and drove an additional four hours to retrieve it.

Like Epstein, Cherington's New England roots run deep. His grandfather was a Dartmouth professor and Pulitzer Prize winner in poetry, while his grandmother "Gumma" was Ben's companion during his visits to campus. Ben's grandmother Rita, his chaperone at Fenway, lived in Cambridge and spent countless hours with him talking baseball.

When Cherington was in the fifth grade, he was shagging fly balls before his game when his coach hit a sinking fly ball to center field. Cherington dove for it, hoping to execute one of those shoestring catches his Red Sox idols had made look so effortless. Instead, he broke his wrist and missed the entire season. That, in addition to breaking his collarbone three times (jumping off bleachers, football at recess, absorbing a check in hockey) accounted for his reputation as the most accident-prone member of the group.

He was a standout pitcher at Lebanon High School and was admitted to the prestigious Amherst College as an English major and a baseball pitcher.

"Ben had average velocity, about 85 mph," his former coach Bill Thurston said. "He knew better than to try to blow it past someone. He liked to throw 5-6 pitches per batter, with no intent of a strikeout. He was so calm, so smart. He would have been a fine college pitcher for us."

Instead, an offseason of hockey and lifting weights left Cherington with a damaged shoulder. Thurston noted his delivery had been compromised and ordered some tests. The diagnosis: torn labrum. Surgery ensued and Cherington's pitching career was done.

It was devastating news, yet neither his mother, his buddies from Meriden nor his new teammates at Amherst recall him discussing it much.

The shoulder injury was the culmination of a series of blows that shook the very foundation of Cherington's world. The first was the revelation at age 16 that his parents were getting divorced, news that saddened and confused him.

Ben Cherington
Cherington is facing a difficult decision to name Boston's new manager, a key piece to make the dream of getting the Sox back on top come true.

"I was shocked there was a problem," Cherington said. "Looking back, there were probably signs, but I was just a kid. I didn't see them."

His sense of security was further shattered by the death of both of his beloved grandmothers within a couple of years of one another.

By the time his baseball pitching career was taken from him, young Ben Cherington was reeling.

"It was a tough time for me," Cherington said. "There was a lot of loss, then I got hurt. I didn't know how to talk about it."

He returned to Amherst for his senior season, but his role had been reduced to a fourth outfielder. Even so, Cherington pushed to get in the lineup. "I felt I should have been playing," he said.

Thurston called on him to pinch-hit during a chilly New England afternoon in April. Cherington went to the plate thinking fastball and deposited one 400 feet for the only home run of his college career.

"I've never seen a team so excited for a guy," former teammate Justin Cronk said. "That home run symbolized everything Ben stood for as a person -- persistent, determined, humble. We were going crazy, but he was the same old Ben."

"I was happy I hit a home run, but it didn't solve anything," Cherington said. "I was still dealing with a lot."

Recasting the future

He recognized he needed a way to stay connected to baseball, so he offered to help with the pitchers, became a de facto student coach.

Jon Cross was a freshman at Amherst when Cherington watched him throwing during fall ball and spotted a flaw in his delivery.

"It had to do with my posting leg," Cross said. "I had never noticed it. My high school coaches never said anything about it. When Ben mentioned it, he did so without a hint of arrogance. He simply told me, 'This is something Coach will pick up on.'"

Cross paid little mind to Cherington's observation -- until that spring, when Thurston took one look at his freshman's motion and barked, "Look at your posting leg. That's not going to work."

Cherington's attention to detail landed him a job with the Cleveland Indians. While he was there, he was given a side project that attempted to determine what constituted a No. 1 and No. 2 starter.

Cherington combined the objective and subjective data and drew conclusions that raised eyebrows in the front office.

"With Ben, there was always a better way to do it, while still being respectful of what was in place," said current Pittsburgh GM Neal Huntington, who back then was the assistant farm director in Cleveland.

David Ortiz and Dustin Pedroia
Dustin Pedroia, right, was one of Cherington's scouting successes, while David Ortiz's future in Boston is uncertain as he hits free agency.

In 1997, when fellow Amherst alumnus Dan Duquette brought Cherington to the Red Sox, he immersed himself in the Sox farm system, delighted in tracking the team's prospects.

One of his success stories during his time there was Dustin Pedroia, who after the Sox drafted him in 2004 was a doughy shortstop with great instincts and a big swing.

"He took this huge hack, but he rarely swung and missed -- it didn't matter what the velocity was," Cherington said. "I saw him crush a ball to left field at the Phillies' spring training facility. I remember thinking, 'Wow, this guy has some power.'"

Pedroia arrived in midseason 2006 to a Sox team that had already established its personality around future major leaguers Jonathan Papelbon, David Murphy, Brandon Moss and Manny Delcarmen. Yet, within a week, all of them gravitated toward the diminutive infielder.

Pedroia struggled when he first arrived in the majors, and Thurston, Cherington's former coach, declared, "Doesn't look like that kid Pedroia is big league material."

"Ben told me, 'Coach, I think you're wrong. He's one of the few guys we have who gets more extra-base hits than strikeouts,'" Thurston recalled. "Of course Ben was right. Pedroia turned out to be a coach's dream."

There are some personnel decisions Cherington would like back, such as trading Cla Meredith, or signing Dominican prospect Junior Frias to a $400,000 contract. Frias, a promising pitcher, never got out of Double-A ball.

Tomorrow is now

The new Red Sox GM is unafraid to swing and miss. He has a weighty list of tasks ahead, among them a new manager, some pitching depth, and offseason visits with his battered players.

The boys from Meriden understand their friend will be busy. They cherish the time they steal with Cherington, like a few years back when he met them at a Pearl Jam concert. Ben arrived in a limousine with Theo, but eschewed the GM's offer of two rows from the stage so he could sit in the cheap seats with his friends.

"It was never 'if' Ben would be a GM' but 'when,'" said Dan McGee. "We always assumed it would be a team like the Kansas City Royals and we'd get rid of all our Red Sox stuff and we'd go to as many games as we could. We wouldn't have to feel bad about asking for tickets because no one else would want to go.

"That was our plan: Let's find a small market and follow Ben."

Cherington had an alternative vision, one he revisited each year while jogging around Boston's spring training complex.

How would he run the Red Sox? He's been planning forever for this, ever since he swung that whiffle ball bat and took his best crack at being Jim Rice. Maybe that's why, in his first official news conference as the team's general manager, he didn't have any notes. He didn't need them. He has committed this journey to memory.

Not all of Ben Cherington's wishes have come true. His path to the Red Sox leads all the way back down that long dirt road to his kitchen in a tiny New Hampshire town, where a little boy with big dreams understood that, in time, if you pay attention to the little things, they just might set you apart.

Jackie MacMullan is a columnist for ESPNBoston.com.