Theo Epstein: “When we do win it’s gonna mean more than just a World Series”

October 26, 2011 – 11:10 am by Chris Fedor

The Chicago Cubs have made some big splashes in free agency that haven’t amounted to much. This time instead of bringing a player to Chicago, they brought a new President of Baseball Operations to run the show in the Windy City. After yet another disappointing season on the North Side the Cubs went and lured Theo Epstein out of Boston. Epstein is seen as one of the better young baseball minds in the business and did a tremendous job during his time with the Red Sox. Some people will point to the misses that he had recently with players that have not lived up to their inflated contracts, but Epstein’s tenure was a huge success and will be looking to do the same thing that he did in Boston: End a championship drought.

However, Chicago might present a different kind of challenge for the 37-year-old with two World Series titles attached to his resume. Unlike in Boston where he was welcomed with a roster full of All-Stars, future Hall-Of-Famers, and a team ready to compete right away, the Cubs are rebuilding again and trying to clean out the organization.

The Cubs have made a huge splash and brought a lot of excitement back to Chicago with this hire, but they haven’t won a title in 103 years. They haven’t been to the World Series since 1945. It will be up to Epstein to put together a title team and reverse the fortunes of a franchise the same way he did in Boston.

Theo Epstein joined ESPN Radio Chicago with Waddle and Silvy to talk about taking the job with the Cubs, how he would describe the last 24 hours, what it would mean to win a World Series with Boston and Chicago, if there will be more pressure in Chicago, what he learned from free agent mistakes, and if he was ever skeptical about taking the job with the Cubs.

How do you describe your last 24 hours?

“Pretty busy I am glad to get the press conferences out of the way. They’re all well and good but have nothing to do with really winning baseball games so now we can move on to the hard work. And trust me there is plenty of work ahead. I was kind of getting flashbacks to nine years ago when I was named GM in Boston, it’s a pretty similar experience. You’ve got the press conference and all the follow up interviews that last for like twenty four hours and then you finally sit down and start cranking with the work.”

Have you ever thought about where you would be put on the sports landscape in the history of executives if you won in Boston and Chicago?

“That’s the sort of ego gratification part of it that I don’t think really gets you anywhere. I can’t say that deep down on some level that didn’t appeal to me but if that was the main reason for taking the job I would be worried about how it would go. The two things I like best about my experience with the Red Sox were one getting on the ground floor helping building a scouting and player development and operations with everyone else in the front office. Defining a Red Sox way of how we were going to run the organization up and down all the way from rookie ball to the majors and putting it into place. Having success drafting players and having them come through the system. The second thing I liked was in 2004 when we won it affected so many people. It meant so much to so many people and I got to see just how it affected the city of Boston. Generations of people with folks leaving Red Sox pennants on gravestones. It was just a transcending experience for the whole region. The Cubs opportunity gives me a chance to hopefully do both of those things over again. The parts I liked the most from Boston I have a chance to maybe do again here. When we do win it’s gonna mean more than just a World Series as you guys know to the folks here. They deserve it and generations have waited, waited, and waited so when it does happen it will mean that much more.”

How do you expect to the pressure to be different here with the Cubs then in Boston?

“Basically they’re similar. You know Boston’s not Chicago and Chicago’s not Boston and every market has its own personality. I had a little bit of an advantage in Boston because I grew up there. So I knew the guys who were asking me questions because I had read their stuff for years. I had a feel for the market. Maybe some things to avoid saying and other things to emphasize. Chicago it will take me a little bit longer. As far as the pressure goes, they’re about the same. You’re dealing with two teams who haven’t won in such a long time and there has almost been a fatalistic sense that has come over the fan base. So when things weren’t going well it was ‘ok here we go again.’ And when things were going well they were waiting for the other shoe to drop. I think the way to combat that is from the inside out. In the end the best way to please our fans is by winning. So from the baseball operations point we’re gonna focus on finding players who want to win because they’re hyper competitive, find players who have each other’s back, find players who want to pull together as a twenty five man unit, who want to win for each other and not necessarily listen to what the media is saying and don’t care about people expecting the other shoe to drop. So that’s how we will combat it. We’re not going to run from the pressure and expectations. We are gonna find motivation from within.”

What can you say to Cubs fan to expect from next year’s team?

“The work of building a foundation is going to take some time. We have to enter every winter no matter what is on the roster or what happened the year before saying what can we do to put ourselves in the best possible position to win. Opportunities to win are sacred. We know our fans feel that way and we feel that way. Our fans deserve it. The interesting part comes when those two interests conflict. If we are faced with a situation where there is something to do to marginally improve next year’s club and make it more competitive but it takes away a lot of resources such as too much payroll or prospects. When it’s time to break that tie I’m going to defer to the long term health of the organization. Simply because I think what Cubs fans really want as much as you’er excited about 2012 and making sure we’re competitive, trust me I’m excited about that too, but I think what you really want is to be competitive every year. You don’t want that one year where things go well and you happen to win ninety two games and a couple series and then you disappear for the next five years. I think what this is all about is building a foundation to have a core that can get us in deep, deep into September and October every single year. Then we can make tweaks each winter to maximize that chance.”

What kind of shape is the foundation in for the minor league and Dominican
program?

“There are really good signs of a new direction. You know the Cubs traditionally have not been really big spenders in the draft and now all of a sudden this year you can tell that they are being more aggressive. They were selecting higher ceiling players who had strong commitments to college and would require bigger bonuses than normal and they went for it. It’s not that we agreed with every selection and every team sees these players different but it was clear that they were committed to it and they followed through by signing the players during the summer. That was a philosophical shift in the right direction in my opinion. Building the academy in the Dominican Republic. Every head of baseball operations and every owner has always talked about a commitment to scouting it but now the Cubs are actually doing it, and it’s my job to make sure we see through to that.”

Can you envision Ryan Sandberg having some sort of role with the Cubs next year?

“That would be way pre-mature to talk about but right now he is a Philadelphia Phillie. He was a great Cub, great player, great guy on all accounts. I’m going to sit down with Mike Quade and get a debrief from him and share my vision for the organization. I’m going to do that with everybody with the organization before we talk about bringing anyone in from the outside. I have to get a feel for what we have here.”

What do you learn as a GM and now President from some of the free agent signings that you didn’t go the way you expected?

“The key to free agency first of all is to recognize that the goal for every organization is to build your system up through scouting and development, so you have so many players coming through where you never have to enter free agency from a position of need or desperation. The ideal is if your third basemen is going to become a free agent hypothetically he is going to get more money elsewhere, you let him go. But you have a 3rd basemen ready who spent a full year in AAA and is big league ready. Maybe had a cup of coffee the year before and he can step right in. If you can do that for every position then you never have to enter free agency in a position of need. From my personal experience that’s where mistakes are made because you talk yourself into needing a player. Like we have a great team but we don’t have a third basemen. If we just had a third basemen that would put us over the top. You might not even like the free agent third basemen but the best one out there starts to look better and better to you and all of a sudden instead of three years you’re giving him four years instead of 6 million you’re giving him 8 million. That’s the way you make bad mistakes. So the way to succeed in free agency is to focus on building the rest of your organization and then be a selective shopper so you can say we are going to be interested in free agents but only the ones that check every box for us. They’re the right age, right position, do the things we like on offense and defense, they’re good character guys, they fit into the clubhouse and we can get them on the right deal. That’s the key. You can’t get yourself into a position where you fill you need a free agent or you’re in trouble.”

Any moment where you thought you were a little skeptical about this job or was it full go the whole time?

“I had to make sure I wasn’t talking myself into it. I had this romantic notion as a kid watching from across the American League at what the Cubs were like and what they represented as a purist I really buy into the tradition, the ballpark, and the fans. The World Series drought was appealing in some respect because it will mean so much more when you do win. But I had to do the work and the research and talk to Tom Ricketts and make sure the reality matched up with my fantasy and I was really happy when I did do the work that it was clear that this was actually a great opportunity and not just something that I hoped was a great opportunity.”

Listen to Theo Epstein on ESPN Radio Chicago with Waddle & Silvy

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