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Theo Epstein opens up about his emotional ride with Cubs

MESA, Ariz. - Theo Epstein is fresh off presiding over his third World Series championship. Epstein won two with the Boston Red Sox, breaking an 86-year drought in 2004 and winning again in 2007.

As Chicago Cubs president, he oversaw a massive rebuild, culminating in November's World Series victory over the Cleveland Indians, ending a 108-year run of futility.

On a windswept Friday afternoon at the Cubs' spring-training complex, Epstein sat down for a question-and-answer session, telling me what the experience was like on professional and personal levels. Here is our conversation.

Q. Many Cubs fans said they could die happy now that their team has won a World Series. Was what happened last year the culmination of your efforts or just the first culmination?

A. I don't look at is as a culmination as much as I look at it as a transformative event.

For fans, it provided joy and redemption and pride and opens the door to a whole new way, I think, to experience Cubs baseball while at the same time validating all the time and energy and passion and love they have given.

And for us, both in Boston and here, people would always spend time worrying what it would be like after you won a World Series. Would it be as much fun? Would it be the same?

It doesn't have to be the same, but I can tell you from experience in Boston, it's better. Everything gets enhanced after you win. There's more interest in the team. There's greater connection, if possible, between the fans and the players. Our players feel they have a special place in the fabric of the city, which they do.

Q. It seemed the Red Sox were no longer as lovable as they were before they won more than one World Series. Do you worry about that happening with the Cubs, or is not being lovable a good thing?

A. There are a few differences. In '04 when we won, we had a really veteran team. Here we have this unique young nucleus of really likable players who all are going to be here for a while. Our fans already have relationships with these guys and will continue to get to know them better and better over the next five years.

Look, I think when you win a lot and you win every single year, there's a certain segment of the country that's not going to care for you because of the Horatio Algers. They root for the underdogs. But I think we can learn from that. I think our players are likable, and that should mean that a lot of folks who were rooting for us in the World Series in '16 hopefully will continue to be on our side.

Q. What was the parade and rally like for you on visceral, emotional level?

A. It was one of the best experiences of my life. There had been so much anticipation about what it would be like to see everyone celebrating and so happy and see the town come alive. It exceeded even our wildest expectations, the degree of passion and the volume of people.

On a personal level, I never wanted to entertain the notion of having to leave Chicago without having been part of a World Series championship. That's one of the feelings I had during the celebration and during the parade, that I did have that weight lifted from my shoulders and just enjoy the whole experience of being in Chicago while the Cubs are a good team.

Q. Was that feeling different from what it was in Boston?

A. Similar feelings, but I'm at a much different point in my life now. I'm more mature. I have kids. I feel like I have a much better perspective on it, that maybe it came too soon in Boston and I didn't appreciate how rare it was, how meaningful it was, how many things have to come together to make it happen. I think I maybe appreciate this one a little bit more.

Q. Do you allow yourself to think about how far the organization has come?

A. At some times I think about that. Joe (Maddon) and I went to dinner (Thursday), and we just started talking about how wonderful a place this is right now, where there is a special feeling around camp. We have high-character players. We give a lot of freedom to them. We really trust them to do the right thing. It really kind of runs itself. Thanks to our players, it means something to be a Cub now.

I think from ownership to the front office to the manager and coaching staff to the players to the minor leagues to the facilities, there's a lot to like about this organization now, and I appreciate it. I'm in a unique spot where I get to see all the levels come together. I don't take it for granted. It has come a long way. I think primarily it's a testament to what our players have done and how supportive they have been to one another and the organization along the way.

Q. What was the most daunting aspect of the rebuild?

A. It was probably around May of 2013 or so when we felt like we had such a talent deficit. We knew we needed six to 10 impact players in order to get where we wanted to go. We felt like we had only one or two. We didn't know where they were going to come from.

Then all of a sudden in rapid succession, we drafted (Kris) Bryant. We made a couple big trades. Other players we had previously acquired had started to blossom. Within about an 18-24-month span, our nucleus really came together quickly. There were some tough moments. As the talent started to come in and change what it meant to be a Cub and change our expectations, the picture really started to crystallize.

Q. The math of the postseason makes it hard to repeat. What should fans realistically expect in the fall or in the season leading up to the fall?

A. It's important not to look past the regular season. If we do our jobs, we will put a team on the field that almost every year can win 90-plus games and get into the playoffs. That in and of itself will give us a chance to win multiple World Series. But if we catch some breaks and respond to adversity the right way and do our jobs well, we hope to be peaking if we're lucky enough to have the opportunity to play in October.

We're not going to win every year. Actually look no further than the 2016 playoffs. We were in the ninth inning of Game 4 against the Giants. We were one inning from having to beat Johnny Cueto to survive. We were down two games to one and hadn't hit at all in two straight games against the Dodgers and came back against them having to beat (Clayton) Kershaw in order to avoid a Game 7. Then we were down three games to one against Cleveland and blew a lead late in Game 7.

Your mortality in the playoffs shows up constantly. I don't want to say that it's World Series-or-bust every year, but I do feel like we're the type of organization that can win every year if we do our jobs and get a few breaks. That's really a testament to how talented this nucleus is.

Q. Would you like to be the 1990s-2000s Atlanta Braves of the late teens and early 2020s, not that you're going to win only one World Series but that you're going to be a team in the postseason every year?

A. I have tremendous respect for the teams that are synonymous with October baseball whether it's the Braves or the Yankees, the Red Sox, Cardinals. I do feel five years from now if the Chicago Cubs are synonymous with October baseball and hopefully winning multiple championships, that would be a job well done.

Follow Bruce's Cubs and baseball reports on Twitter @BruceMiles2112.

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