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Theo Epstein on Ryan Dempster, changing a clubhouse culture and flowers for J.D. Drew’s wife

Cubs president of baseball operations and former Red Sox GM Theo Epstein [1], in an interview on WEEI’s Red Sox Hot Stove Show on Thursday, touched on a number of topics of relevance to his former team. Among them:

He praised the deal [2] that sent Adrian Gonzalez [3], Carl Crawford, Josh Beckett [4] and Nick Punto [5] to the Dodgers in exchange for five players, foremost Rubby De La Rosa and Allen Webster. He also suggested that the Red Sox organization appears unified in its decision-making in the aftermath of the deal, which he described as “a great thing for the franchise.”

— In an offseason in which the Sox have been reluctant to pursue Adam LaRoche [6] in no small part because he would cost the team a second-round draft pick, Epstein discussed the increased value of a second-round pic [7]k under the terms of the new Collective Bargaining Agreement.

— Epstein also discussed right-hander Ryan Dempster [8], who was dominant last year for the Cubs before a deadline trade that shipped him to the Rangers, and who was ultimately signed by the Red Sox as a free agent to a two-year, $26.5 million deal.

“I think Red Sox fans are going to love him. He’€™s another pitcher who’€™s been extraordinarily consistent and healthy,” said Epstein. “He takes the ball 30-plus starts every single year. Very, very competitive. He’€™s really evolved as a pitcher. Earlier in his career, he was a guy with great stuff, a terrific swing-and-miss breaking ball, not always known for his command, more of a power guy than a finesse guy. 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. Now he’€™s more of a pitch-maker. He hit his spots consistently all year long. Really executed with his split-finger to keep hitters off balance. Even when he didn’€™t throw a good split, it’€™s just the type of pitch that hitters don’€™t get good swings at. They don’€™t center it. He’€™s smart, he knows what he’€™s doing, he’€™s still got solid, average stuff, the difference-maker in the split, he’€™s competitive, a really great teammate and a guy you want out there on the field. He always has fun and keeps things positive for everybody. He knows what he can do, knows what he can’€™t do, and should be a very effective, consistent, effective pitcher for the Red Sox.”

Mike Napoli [9] remains in a state of limbo more than a month after agreeing to a three-year, $39 million deal with the Sox, due to health issues that emerged during his physical. While Epstein did not have knowledge of the specifics of Napoli’s situation, he did offer insight into his own protracted negotiations to sign J.D. Drew after his five-year deal required measures to address a shoulder concern that emerged in the outfielder’s physical.

“If things come up as part of the conditions being met in the deal and new information, then usually the sides have to just sit down together and hammer things out in light of new information,” said Epstein. “Some things came to light in the course of [Drew’s] physical that just meant that we had to work on some language in the deal that was fair to both sides, that would protect the club, that wasn’€™t overly onerous. It got a little bit awkward. I remember that period of negotiation went through the holidays. It could have been unsettling for J.D. and his family. I remember we sent some flowers to his wife and apologized. We were able to work something out that really did protect the club and at the same time was fair. It didn’€™t end up coming into play. Everyone felt better about it when it was done, then we went out and won the World Series [10] that year, so things were fine and it was forgotten. It can be an awkward situation in general. I have no idea at all what’€™s going on in this specific case, but usually it’€™s just a matter of the club and representatives sitting down and working things out.”

— Epstein will be in Boston next week to take part in the Hot Stove Cool Music events that benefit his non-profit Foundation To Be Named Later. As part of the events, the annual baseball roundtable discussion will feature a conversation about changing a clubhouse culture (a conversation that will include Epstein, Sox GM Ben Cherington, Sox manager John Farrell [11], Orioles manager Buck Showalter [12], Sox assistant GM Mike Hazen and Hall of Fame writer Peter Gammons [13]).

Epstein reflected on the challenges and importance of creating and sustaining a successful clubhouse culture, based on both his experiences with the Red Sox and the Cubs.

“I think it’€™s fundamentally important but it’€™s really hard to define. It’€™s almost an amorphous thing,” said Epstein. “You can set out to change the culture and try to institute certain changes, bring in certain people, identify some priorities and values, but it’€™s just a really hard thing to accomplish. I don’€™t think there’€™s any one thing you can do to do it. But certainly it takes an organizational commitment and you have to stay on top of it or it can get away from you.

“I think, my two experiences trying to set out and sort of acknowledge there was a need for change, was back with the Red Sox, I joined the Red Sox right after that 2001 season where clearly there were some things wrong and some culture change needed. Then took over as GM after the 2002 season, and it did become a priority to bring in some personalities like [David] Ortiz [14] and [Kevin] Millar, players like that, who would sort of embrace the role of being a Boston Red Sox [15] and wouldn’€™t let the outside influences bother them, would really create significant bonds with their teammates, sort of establish a certain way 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 well established, then sort of morphed into a little bit more of a professional culture as things got a little bit out of control as there was some success. Then certainly at the end some things got away from us inside the clubhouse. So it was interesting to see how things evolved.

“I’€™ve hopefully taken some of those lessons with me to the Cubs and tried to use them here as we had 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 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 wasn’€™t a single player who complained. The players had each others’€™ backs. Nothing leaked out that shouldn’€™t have leaked out. They prepared hard, they played hard, they certainly covered for each other. We got rid of a couple of the players who were causing some of the issues. I think that was important. But really, ultimately, there’€™s 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.”

To listen to the complete interview, click here [16]. For information on the Hot Stove Cool Music events, which include the baseball roundtable and a concert, visit the website of the Foundation To Be Named Later [17].