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Epstein was an old pro

General manager's decisions key to building winner

Multimillion-dollar baseball dealmaker by day, garage-band guitarist by night, Theo Epstein found refuge one brutally cold night last January a few blocks from his childhood home in the warm cocoon of a couple thousand Red Sox fans stoking the embers of their unrequited dream: a new world championship banner fluttering over Fenway Park.

They called it Paradise, the rock club where they convened on Commonwealth Avenue, and the faithful who braved the chill that night could only hope -- as their parents and grandparents had hoped -- that the Sox by October would enter baseball's promised land.

At 30, Epstein was the vessel of their dreams, the youngest general manager in the game. And as the flannel-clad, moonlighting rocker faced the yearning masses at the annual "Hot Stove, Cool Music" benefit for the Jimmy Fund, comedian Seth Meyers put the question to Epstein in terms the bluntest Bostonian could grasp.

"Are the Red Sox this year going to be awesome, wicked awesome, or wicked [freakin'] awesome?" Meyers said.

"I grew up in Boston," Epstein said. "I know the right answer. We're going to be wicked [freakin'] awesome."

And so they were, thanks largely to a kid who grew up in Brookline, a short walk from Yawkey Way, dreaming of a life in sports, and built a team that triumphantly ended an epic struggle for baseball supremacy with the first Sox championship since 1918.

"It's like something out of a movie, seeing how thrilled everyone is," Epstein said yesterday, after the Sox returned from St. Louis and watched scores of drivers jump out of their cars to applaud them as police escorted them from Logan Airport to Fenway Park. "Seeing the joy on their faces made it a ride we'll never forget."

From Paradise to the pearly gates of the national pastime, Epstein transformed a team that for several years only flirted with championship glory into a band of wild-haired, Harley-riding, tradition-busting renegades who played the game better than any team in the land.

It was no simple task. For the first time in his life, Epstein swallowed a sleeping pill as the walls closed in on him amid the midseason pressure. The Sox had slipped into a months-long run of mediocrity with no end in sight, and with his players generally feckless in the field and dangers to their cause on the basepaths, Epstein designed a daring gambit.

"I definitely have a few more gray hairs than I did in spring training," he said. "You want so much to do the right thing and hope it turns out for the best."

Epstein traded shortstop Nomar Garciaparra, the most popular Sox star in New England since Ted Williams, for two players who possessed none of Garciaparra's fame but many of the skills the Sox lacked: Montreal shortstop Orlando Cabrera and Minnesota first baseman Doug Mientkiewicz. In a separate deal, he also acquired Los Angeles outfielder Dave Roberts.

"After a period in which we had played .500 ball for more than 80 games, he identified our weaknesses and he dealt with them in a bold way by trading the face of the franchise," principal owner John W. Henry said. "It was a very risky move."

It was so risky that Epstein needed the sleeping pill to get through the night after the trade, then he slinked for a while through the streets of Boston as if he were incognito, to spare himself from the possible backlash.

"We did the trade for the right reasons, but there would have been hell to pay if it didn't work out," Epstein said. "If we hadn't made the playoffs and the Cubs had, there would have been dire consequences for the club and the people I care a lot about."

Henry had calculated the risks with help from Bill James, a senior adviser widely considered the godfather of quantitative baseball analysis. The findings supported Epstein's move, as did the results on the field.

A championship team was born, though Epstein planted the seed the previous winter when he stunned the baseball world by acquiring Arizona's Curt Schilling, one of the greatest big-game starting pitchers of his generation, and Oakland's Keith Foulke, the preeminent closer last year in the American League.

The boldness of Epstein's moves came as no surprise to those who know him best. To his family, he was born to the challenge. While his peers watched cartoons, Epstein read the sports pages. He insisted on playing baseball at Brookline High School even though he was a natural at soccer. He edited the sports pages of the Yale newspaper while others studied the classics. And while his fellow Yalies fanned out in academia or the corporate world, Epstein tackled low-paying drudge work as a public relations assistant for the San Diego Padres before he worked his way up to the director of baseball operations under team president Larry Lucchino and picked up his law degree part time at the University of San Diego Law School.

By 28, Epstein was the 11th general manager of the Sox -- and the youngest GM in major league history. Perfect, thought his father, Leslie Epstein, a former Rhodes scholar who heads the creative writing department at Boston University.

"When Alexander the Great was Theo's age," the elder Epstein said, "he was general manager of the world."

Fair enough, but Henry had some reservations. Henry has made fortunes for himself and many others with his expertise at managing risks in the financial markets.

"Whenever you take risks, they should be calculated risks, so we try to calculate the risks before we take them," Henry said. "Hiring Theo was a calculated risk, but it was one we were very, very comfortable with. The only risk we thought of was that we would be criticized for placing a team of this magnitude in this particular market in the hands of someone who was 28 years old. But we were very confident that he was the right guy."

It was November 2002, and Epstein had lobbied for Oakland's general manager, Billy Beane, to succeed Mike Port, who had served as interim Sox GM for eight months after Dan Duquette was fired. Beane declined the job, after accepting it 24 hours earlier, prompting Epstein to push for ownership to hire Toronto GM J.P. Ricciardi. But Ricciardi signed a long-term contract extension with the Blue Jays.

"Theo was his own third choice," Henry said.

And maybe the perfect one, considering the moves he made and the personality his team developed. Epstein balked at first when Johnny Damon launched the team's run toward baseball irreverency by reporting to spring training so long-haired and bearded that he looked like Jesus of Nazareth.

Soon, Damon, Foulke, Kevin Millar, and others showed up riding Harleys, even though some of their contracts prohibited motorcycling.

Had Epstein clamped down as Yankees owner George Steinbrenner almost certainly would have, he risked losing the team's loyalty, a potentially damaging twist. But he ultimately joined manager Terry Francona and the ownership group in endorsing the team's freewheeling style off the field as long as the players performed to their potential on the field, which they did.

Epstein credited Henry and his fellow owners for backing him.

"They're not afraid to fail," he said. "We're not afraid to do something stupid."

The Sox players responded enthusiastically.

"They said all along, `Just go out there and play well and you guys can grow whatever hair you want, grow whatever kind of beards you want,' " Damon said. "It's something the whole nation has taken watch of. The biggest thing is, when people look at our team, they can see that we're having a lot of fun."

So are their fans, who will join them in paradise tomorrow at a celebratory parade for the ages. 

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