Boston success informs, fuels Epstein

The "overwhelming" feeling of the 2004 Red Sox title is one Theo Epstein wants to savor in Chicago. Brad Mangin/MLB Photos via Getty Images

BOSTON – If there’s one thing Chicago Cubs president Theo Epstein brought with him from Boston in 2011 it was an understanding. An understanding of what an iconic sports franchise means to its fan base and to its city. He knew all about it growing up in New England, then felt it deeply when, in 2004, he orchestrated the Red Sox's first World Series title in 86 years.

That was a decade ago, but it’s something Epstein, now 40, said he will never forget because it meant so much to so many.

“Driving from Logan [Airport] to Fenway Park the day after we won, passing cemeteries, seeing Red Sox hats and pennants draped over tombstones and realizing what we all accomplished together impacted multiple generations and would profoundly change people’s lives,” Epstein said recently. “It was overwhelming.”

That’s the same sort of deep impact a Cubs World Series title would bring to Chicago diehards, and Epstein knows it. He won’t get to relive his Boston memories this week, as family matters will keep him in Chicago when the Cubs play the Red Sox the next three nights, but the upcoming series did give him a chance to reflect on those early years as an executive and how far he’s come.

“When I got that job, I was 28 and still learning how to be an adult,” he said. “I was not emotionally mature enough to handle the weight of that job. I had to learn on the fly. I have much stronger footing. I know what I’m dealing with. I know myself better. I know the job better. I’m a better executive."

Cubs fans should be grateful for the experience Epstein got in Boston because a first-time general manager would probably need a life jacket to navigate the Cubs' current situation. Between financial issues and city politics, the team isn't exactly the model of a well-oiled machine. But that doesn’t mean the baseball department isn’t doing what it can to move the organization closer to that ultimate goal. Epstein has stripped the Cubs down in a way no other big-market team has ever seen, but the trials and tribulations of the past few years might actually be a blessing in disguise.

“Given the talent and financial realities of the situation, once we understood them, there was no alternative here, and I think it’s going to be -- in the long run -- the best thing that’s ever happened to us,” Epstein said.

That’s an important statement. Yes, the Cubs might have had some young, international additions such as Yoenis Cespedes or even Yu Darvish if they could have spent the way the Red Sox were spending when Epstein worked there. But how would they have rebuilt a farm system or flipped aging veterans for prospects if they were winning a few more games? Only in hindsight can we see the parity that has taken over in baseball and make the assumption that the Cubs could have contended these past few seasons. Maybe they would have had a run in them with some new, talented players to go along with what was already on the team, but that would have amounted to exactly what Epstein doesn’t want: a quick fix. Then where would the Cubs be?

“The biggest difference is we had a third of the roster that was already elite over there [in Boston], including some Hall of Fame-type talent,” Epstein said. “We felt like we could make an immediate impact by focusing on the whole roster and acquiring some undervalued talent.”

That was the plan during Epstein's first few years in Boston because a foundation was in place and the Red Sox could spend. When Epstein took over in Chicago, he quickly realized he had neither resource going for him, so he went big on the rebuild while waiting for money to arrive.

“The good fortune of winning the World Series early bought us some security to invest in scouting and player development,” Epstein said of his Boston tenure.

With the Cubs, Epstein and his front-office charges went directly to scouting and development because it was the only choice. He might not admit it, but not being beholden to a certain win-loss record must feel liberating for an executive. Of course, there will be a day when he’s held accountable for the Cubs’ place in the standings, but right now he can build the franchise without looking over his shoulder. In Boston, the 2004 title bought him the time to do it through the farm system, and when 2007 came along there was a very different feel to the Red Sox team that won the World Series.

“We went from one homegrown player in 2004 to 12 in 2007,” he said.

The Cubs are hoping to be the 2007 Red Sox someday -- or even the 2013 version, which won after adding minor pieces, like Epstein did following a near-miss 2003 season. The process has worked in Boston, and it all leads back to what the youngest executive in the history of the game started there. It’s the same thing he wants in Chicago.

“We’re starting from the bottom,” Epstein said. “It’s more grassroots. The starting line was further away from the finish here than in Boston.”

As you can imagine, Epstein will never forget the “moment the ball went into the glove” to end the 86-year Red Sox championship drought in 2004, and he’ll never forget those tombstones he passed the next day. He wants to feel it all again.

“That’s the best part of this job,” he said. “I’m lucky that I could take another job where there’s that goal again. We do say when it happens, not if. When it does, it will be like picking between your children. They’re all special.”