For Cubs' Epstein, connections with Boston are real

History, both ancient and recent, will be hard to avoid this week as the Cubs visit Fenway Park for the second time in four years.

When the Cubs played the Boston Red Sox at Fenway in 2011, it marked the first regular-season meetings between these stalwart franchises in the National and American Leagues, respectively.

At the time, Theo Epstein probably had no way of knowing that he was in his final season as general manager of the Red Sox.

An epic collapse in the final days of the 2011 season set off a series of events that led to Epstein leaving the Red Sox as general manager and coming to Chicago as president of baseball operations of the Cubs.

So this week's three-game series should hold some extra meaning for Epstein, who will not travel to Boston because of personal business in Chicago.

A few days ago, I sat down with Epstein in the stands at Wrigley Field and chatted with him about his feelings for Chicago and Boston, where he spent most of his life and will always be known for overseeing two World Series titles with the Red Sox, breaking their so-called “curse.”

Q. After almost three years here, do you feel like a Chicagoan?

A. Yeah, I do. I'll always be a Bostonian, and that will always be “home” home for me. But I feel that this is home as well. I'm a lucky guy. I can call two of the great cities in the world home. I've really enjoyed my time here, and this is where I want to be.

This is a great place. It's so livable for families.

Q. What do you see as the differences and similarities between the two cities and their fan bases?

A. The biggest difference by far is size. Boston is so small you can walk the entire city. It's intimate that way. I didn't appreciate how big Chicago was before I moved here.

It's massive. I think it's a nice balance because it still feels intimate the way Boston does, unlike New York. It's really livable.

As far as the fan bases, the biggest difference by far, and I can only say this because I am a Bostonian, is that the fans here have that more natural optimism. There's this Midwestern sensibility where they're looking to cheer players and looking for things to go well.

In Boston, probably because of our Puritanical roots back there, the sky is always falling; we're waiting for the other shoe to drop. There's always a tension.

Even when things are going well, there's this anticipatory tension about what might be right around the corner.

Q. Has anything about the whole Cubs experience surprised you?

A. I grew up talking about the Red Sox every night at the dinner table. So I knew it was one of those institutions that resonated with families right up there with any of the great institutions. It was a fundamental part of family life.

I guess I didn't appreciate the value that's placed here. A lot of families kind of define their daily rhythm based on the Cubs games and how the Cubs are doing, meeting up at Wrigley.

It just makes me excited because of the impact this team can have on a city where when we win the way I think we're going to win, and that's not with mercenaries but with players fans really get to know and hopefully play together for a decade and a whole generation of Cubs fans can get to know them, love them and relate to them.

I think it will be a great thing for the city. I'm excited about it. It makes us want to do our jobs really well.

Q. Do you believe the fans are buying in?

A. There are always going to be fans on both sides. Sometimes the most negative fans can be the most vocal. By and large, I've been really impressed and appreciative of our fans and their patience and their understanding and their willingness to look at the big picture.

We haven't given them an acceptable product at the big-league level. I think they realize that in some sense it's a means to an end and that they've diverted some of their attention to some of the good things happening in the organization as a whole. We'd love to reward them.

Q. You obviously take pride in the two world championships in Boston. Do you look back with any pangs of regret over how your time there ended?

A. With some time and perspective, I think the way it ended was the way it ended. When you're somewhere for 10 years, there are going to be great moments, and there are going to be painfully disappointing moments. I couldn't ask for more out of the 10-year run that we had there.

Yeah, the way 2011 ended was horribly disappointing, but I also look back at the last couple drafts we had there. I realized that those players are going to be playing in Boston for a long time.

A lot of guys I worked with are still there and have been with that organization for a long time. So I feel, as a whole, the time I got to spend in Boston and what's left there from that time period, I couldn't be prouder.

Q. When the Wrigley Field renovations finally get done, you will have worked in two iconic ballparks that have survived into the modern age. What is it like going to work in places like that?

A. I'm so lucky. I'm really a traditionalist at heart, baseball wise. There probably wasn't a day that I walked into Fenway Park and went down to the clubhouse where I didn't think about the fact that Ted Williams walked down the same corridor. I really appreciated that.

I think about that here many times. At the same time, I reserved the right be a bit spoiled at times. I like having the best for our players in the clubhouse. I like them to be comfortable, and I like to be comfortable.

If we can pull it off and preserve everything, that's great. If we can be in Wrigley for 100 years and still give all the different constituencies the best of the best of the best and the most modern amenities around without being too conspicuous about it, then we'll really strike the right balance.

Q. In the end, would you like to be known as that guy from Boston or as someone who won in both Boston and Chicago?

A. If at the end of the day I'm associated with both teams, I'll be very proud. More than anything, it would be great someday to look back and think that I was a small part of helping to bring a World Series to two places that hadn't gotten to experience it for a long, long time. That will be the most meaningful thing for me.

bmiles@dailyherald.com

Cubs scouting report

Cubs vs. Boston Red Sox at Fenway Park

TV: Comcast SportsNet Monday and Tuesday; WCIU Wednesday

Radio: WGN 720-AM

Pitching matchups: The Cubs' Jake Arrieta (4-1) vs. Jake Peavy (1-6) Monday; Edwin Jackson (5-8) vs. Clay Buchholz (3-4) Tuesday; Travis Wood (7-6) vs. Brandon Workman (1-1) Wednesday. All games 6:10 p.m.

At a glance: The Cubs are 4-5 all time in regular-season play against the Red Sox. They lost two of three at Fenway Park in 2011. Both teams enter the series having endured problems on offense. The defending world champion Red Sox entered their Sunday night game at Yankee Stadium last in the American League in runs scored and slugging percentage. They were 13th in batting average and eighth in on-base. Mike Napoli went into Sunday with a line of .275/.390/.459, while David Ortiz led Boston in homers (18) and RBI (49). The Cubs are 15-26 on the road, and this begins a tough 11-game journey that also sends them to Washington and Cincinnati. The Cubs, who were off Sunday, were 14th in batting average and OBP and 13th in runs scored.

Next: Washington Nationals at Nationals Park, Friday-Sunday

— Bruce Miles