Theo Epstein Talks Cubs on WEEI in Boston

Theo Epstein joined Rob Bradford, Alex Speier and Kirk Minihane during Red Sox Hot Stove Show (WEEI in Boston) on Thursday night. The Cubs’ President of Baseball Operations discussed a variety of topics from  his first two off-seasons with the Cubs to the signing of Edwin Jackson to Anthony Rizzo to the importance of the draft under the new CBA and what potentially losing a pick to sign a player tied to draft pick compensation means.

Theo, good evening. How are you?

Theo Epstein: Hey, good. Thanks for having me on guys.

How is season two, this second off-season with the Cubs now that you’ve been there for a while? How is it different from that first one? It seems at first glance that you guys have been more active in this off-season.

TE: Um, maybe a little bit. It’s always different the second winter with a new organization. The first winter you are spending most of your time getting to know the ins and outs of the organization, the personnel and you don’t have as much firsthand knowledge of the players. Certainly not having seen them play day in and day out for yourself and it is especially true of your own minor league players. So there is more of a comfort level any time you’ve had a full calendar year in a new organization. We are at a slightly different point. We are certainly still in our building process and every move that we make is certainly toward an eye for the future. But we are hopefully a year further along. We have a few more core assets than we did a year ago and we can start to be a little more aggressive trying to continue to build that core.

Theo you just locked up Edwin Jackson to a pretty good contract and I’m just curious about what you saw in him and also what you saw in Ryan Dempster when he was with you that maybe Red Sox fans can expect.

TE: Okay, I’ll answer the Jackson part first. First and foremost, Jackson is the right age. He is still a player that has plenty of prime years left. He’s just 29 years old. He’s been around a while because he broke in so young, but still 29. Of all the free agents he’s been the healthiest, knock on wood, one of the most consistent, one of the most durable, never really had an arm problem and because he’s bounced around so much from team to team he’s a little bit underrated for his consistency. He’s been a solid middle of the rotation pitcher for many years and on top of that he’s mixed a few outstanding seasons. So of all the bet in free agent pitching, which is not a bucket you want to be diving into too often, he’s really one of the safest, relatively speaking, Someone still with elite stuff and somebody we think can be in the middle of our rotation for years to come. With our organization there is a bit of an in balance. We have a lot more depth with our position player prospects than we do with our pitching prospects. As we look forward to future years and the desire to be competitive, we understand it’s really next to impossible to build an entire rotation over the course of one winter or even two winters. So, we really had to start the process of picking our spots to bring in starting pitchers when they were available. If, they were healthy, talented, and the right age. So, Jackson really checked a lot of those boxes for us and he was available for a fair value relative to the free agent market.

TE: On Dempster, I think Red Sox fans are going to love him. He’s another pitcher who has been extraordinarily consistent and healthy. He takes the ball for 30-plus starts every single year. Very, very competitive and he’s really evolved as a pitcher. I think earlier in his career he was a guy with great stuff, with a terrific swing and miss breaking ball but not always known for his command. More of a power guy than a finesse guy and as he’s matured he’s a different guy now. He came up with a split, which was a huge pitch for him last year and now he is really more of a pitch maker. He hit his spots consistently all year long and really executed with his split finger to keep hitters off balance. Even when he didn’t throw a good split, it’s the type of pitch that hitters don’t get good swings at. They do not center it. So, he’s smart, he knows what he is doing, he’s still got solid average stuff and the difference maker is the split. He is as competitive of a guy as you want out there. He’s a great teammate and great person of the field. He always has fun and keeps things positive for everybody. He picks his spots and knows what he can and can’t do. He should be a very effective, consistent pitcher for the Red Sox.

Theo, one of the reasons it’s been kinda interesting to watch your off-season and that of the Red Sox because I think that in some respects they’ve taken very similar courses. Just the idea that the Cubs and Red Sox enter the off-season in similar places with regards to team building was interesting. I guess it kinda stems back to the Red Sox making that blockbuster deal with the Dodgers. Obviously respecting the fact that you don’t want to get too much into what the Red Sox have been doing since you left, it’s still worth asking on just the broad level. When you saw the Red Sox make that deal with the Dodgers, trading Adrian Gonzalez, Carl Crawford, and Josh Beckett to L.A., how stunning was that for you to see that they had done that? And to you what did that say where the Red Sox were?

TE: I think everyone in the industry was surprised at the scope of the deal when it became clear just how many players were involved. But you know, I really like that trade because I am a big fan of the young talent they got back. We spent a lot of time scouting the Dodgers’ system because we had some possible fits with them. They were interested in Dempster at the deadline. It’s hard to make any trade these days where you can acquire two young starting pitchers the caliber of Webster and De La Rosa. I think so much was made of the players going from Boston to L.A. and the vast amounts of payroll that suddenly became available to the Red Sox but I think that not enough was made of the young talent that came back. Besides the two players that I have mentioned, they have already used a couple of other players in deals this winter. But I think Webster and De La Rosa being the key to that deal if those two  develop into the core starting pitchers they can be it’s going to be a transformative deal. The payroll they freed up was remarkable in its own right. It’s an interesting dynamic and we are experiencing the same thing to a certain extent but having available dollars today, this moment in time, with this marketplace dynamic, is not what it was 10 years ago or even five years ago. There was a time when you really had to cling to payroll flexibility because there was so much you could do with it. You had the market, you had the catbird seat in the market and you could really pick and choose what you wanted to do. If there was a player out there you got him because you had the most payroll flexibility. If you had a good farm system, as the Red Sox do, and payroll flexibility, you could just about do anything you wanted to do in trades. These days with the TV money and things going on in the game there are a lot of teams with money to spend and there’s only so many ways to spend it. The new CBA really limiting clubs flexibility to allocate those resources to the amateur market or the international market. There are a lot of teams with money to spend and fewer and fewer quality free agents becoming available so, just having money to spend does not necessarily put a franchise in a great position anymore. So I think the underrated part of that deal for the Red Sox was the young pitching coming back. I think that will serve them really well for a long time to come.

Theo Epstein joins us on the Hot Stove Show on WEEI. Theo, last summer you talked about the monster that the front office had to deal with at times. I guess two parts. One, the elements of that said monster, do you feel they still exist? If you do, how do you feel that Ben Cherington is doing dealing with that?

TE: Well, I’m not in a position to know that or to comment on it but since you just asked about the deal. I think if that trade was an indication that the entire organization is on the same page going forward and is a really united front and that they are prepared to invest in the future together and take a long view together than I think it’s a great sign for the franchise. It sure seems that way so that’s terrific for everyone involved. Ben has always been someone with great perspective and great wisdom and the ability to look at the big picture and it seems that everyone is putting their faith into him. I think the outlook of franchises is based on what they’ve been through. We were in a position where we were having tremendous success year in and year out and averaging 95 wins or so. When you are doing that it can be hard for everybody to agree on looking at the big picture and the long haul. But after you go through some adversity and you have some deals that don’t work out, and you miss the post-season, especially if you go through what the Red Sox went through last year, which was so traumatic I’m sure for everybody I think that there can be a silver lining where it can make priorities more clear and can unite people behind a common strategy. From a far, it looks like everyone is united and everything is going in a great direction as long as it is known there is going to be some patience involved.

Theo around these parts we are still waiting on the Mike Napoli situation to get resolved. We talked to J.D. Drew a couple of weeks ago and he was very complimentary in the way that his 52-day ordeal kinda went and how he had a lot of faith that was going to get worked out. If you could kinda go through what in general terms and what goes on behind the scenes in regards to something like that.

TE: You know I shouldn’t get into too much detail about it but in just real general terms. If things come up as part of the conditions being met in the deal with new information then usually the sides just have to sit down together and hammer something out in light of that new information. That one I can talk about because that contract is over now. There were some things that came to light in the course of the physical that just meant we had to work on some language in the deal that was fair to both sides that would protect the club. It wasn’t overly onerous. It got kinda awkward. I remember that period of the negotiations went through the holidays and it could have been unsettling for J.D. and his family. I remember we sent some flowers to his wife and apologized and we were able to work something out that really did protect the club but at the same time it was fair and it didn’t end up coming into play. Everyone felt better about it when it was done. We went out and won the World Series that year so everything was fine and it was forgotten. It can be an awkward situation in general and I have no idea at all what’s going on in this specific case. Usually it’s just a matter of the club and the representative sitting down and working things out.

Clearly that was your first indication, in direct terms, of J.D. Drew’s unflappability and his even-keeled nature.

TE: I think the industry was aware of that from probably the time that he was an amateur at Florida State to the first time he was drafted. He doesn’t get bothered by much.

One thing that has been interesting to see from a far, as I alluded to, it does seem you guys are kinda moving with similar priorities as the Red Sox, namely signing a lot of guys who require relatively short-term commitments that haven’t cost you a draft pick to this point. I’m just curious, since you do have that protected number one overall pick, how valuable is a second round pick in the new baseball landscape and how important is that when you still have a protected pick to still protect that second round pick?

TE: It’s real important now and probably more important now than it used to be for several reasons. One, you don’t have the amount of compensation picks that you had in the past so that second round pick for us is really where a high sandwich pick would have been in the past. So it really doesn’t matter what round you are picking in, it matters what number it is. We are protecting more than a second round pick, we are really protecting a really high sandwich pick and that’s the case for most teams. I think they will look at it that way. The other thing is something you guys alluded to earlier, there are not multiple paths into the amateur market place anymore. In the past you could give up a high pick and realize you were going to over pay someone later on. You could give up a couple of draft picks and realize you could just go out and try to dominate international free agency that year. You just don’t have the ability to do those things anymore so when you surrender a draft pick and the pool space that goes with it you are really admitting that you are not going to have an impactful draft that year as you would otherwise and that is something that is really hard to do. Given the price of free agents these days and just how meaningful it is to develop your own talent and have that player under control for six years. It’s really hard to try to say we are trying to build a healthy organization but we are going to do it while admitting out draft isn’t going to quite be as impactful this year. I think you are seeing a real premium placed on the draft picks and the pool space that goes with it for good reason. I think it’s a little bit unfortunate that the effect it has had on certain free agents. There is no rhyme or reason to it. The single best thing that can happen to a perspective free agent is platform years and getting traded because it removes the burden of the draft pick compensation. I’m sure that is something they will look at going forward.

Having said that, could you see yourself allocating that pick to any remaining free agents this off-season?

TE: I don’t want to talk specifically about the remaining free agents or our plans in general but I will say that you cannot be dogmatic about it. Clearly there are Major League free agents that are talented enough to justify surrendering a first round pick and certainly a second round pick. You are acquiring the assets. If the contract makes sense then you are getting more in the player’s services and potential trade value for that player, something that is more valuable than what you are surrendering in terms of dollars and the draft pick certainly would make sense. It all depends on not just the player but the contract and then potentially what you get out of the player in terms of contributions on the field or potential trade down the road.

Theo obviously Anthony Rizzo has been highly regarded around these parts for a while and if he wasn’t he would be involved in such a big trade like he was. Has his progress and how quickly he’s kinda evolved over the last year surprised you or is it about the track you thought he might take?

TE: By in large he’s on the path we projected for him from the time he established himself in our system. I think the remarkable thing about what he has accomplished is just how quickly he made a significant adjustment with his swing. When he went out to San Diego and crushed Triple-A and then got promoted in June of 2011 he came up and got into some bad habits really quickly with the Padres. Part of it was trying to do too much and part of it was playing in a park that is just death on left-handed power hitters. He started to over-swing and really go an uphill plane, a dramatic uphill plane going in his swing and his bat was almost never in the zone. He had a really high finish and it was hard for him to impact the baseball to the point where there were some respected evaluators around the game that thought he was not going to make it based on the swing and just how fundamental the adjustment was that was needed. We traded for him and tried to buy low on him last winter because he came up and failed in 150 or so plate appearances. We bought low on him and we thought it would take a little bit of time for him to make that adjustment and planned to send him back to Triple-A. Well, Anthony being the person that he is took it on himself to make that adjustment as quickly as possible and worked his tail off over the winter and really leveled his swing out, lowered his finish, calmed himself down in the box and from the moment he showed up in Spring Training it was a completely different swing. As a 22-year old, we worked his swing in a really fundamental way and took it into the big leagues and it’s just not something you see done with a lot of success too often. I think that instant transformation was really rare. But the general path that he is on he is still showing the same pluses and minuses to his game that we projected for him when he was with the Red Sox. He is just someone that is going to work hard enough to continue to improve over time and has a chance to be an elite player.

Talking to Theo Epstein, Cubs President of Baseball Operations. Theo you’re coming back next week for the Hot Stove, Cool Music Event. The roundtable this year is about changing a baseball culture. It seems like that has been a driving force for the Red Sox certainly this off-season and that was obviously something you obviously placed a great priority on with the Cubs over the last, whatever it is, 14 months or so. How important is it to change a baseball culture where you’ve kinda been through a traumatic run of losses and how much of that was on the forefront of what you tried to accomplish in your first off-season as the Red Sox GM back 10 years ago?

TE: I think it is fundamentally important but it is really hard to define. It is almost an amorphous thing. You can set out to change the culture and try to institute certain changes and bring in certain people, identify some priorities and some values but it is really a hard thing to try to accomplish because there is not one thing you can do to do it. But certainly it takes an organizational commitment to try to stay on top of it or it can get away from you. I think the two experiences trying to set out and sort of acknowledge that there was need for change. I joined the Red Sox right after that 2001 season and clearly there were some things wrong and there was some culture change needed. Then took over as GM after the 2002 season and made it a priority to bring in some personalities like Ortiz, Millar and players like that to embrace the role of being a Boston Red Sox and wouldn’t let some of the outside influences bother them and would really make significant bonds with their teammates and establish certain ways of doing things in the clubhouse that would serve the team well through the grind of the season under the spotlight. I think that really helped and became established and sort of morphed into a more of a professional culture as things got out of control after there was some success. In the end some things got away from us inside the clubhouse. So that was interesting to see that evolve. I am hopefully taking some of those lessons here to try to use them with the Cubs. We have a culture that really needed to be transformed into a winning culture. Even though we lost 101 games last year, the clubhouse that Dale Sveum and the coaching staff and the veterans helped establish that really was a winning culture. I know it sounds ridiculous to call it a winning culture in a season like that with 101 losses but there was not a single player who complained. Players had each other’s backs, nothing leaked out that should not have leaked out and they prepared hard, they played hard, they certainly covered for each other. We got rid of a couple of players who were causing some of the issues and I think that was important. I think ultimately there is only so much the front office can do. It really falls to the manager and some of the veterans to truly establish what’s called the culture of the clubhouse.

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