Cashman and Epstein Entertain With Behind the Scenes Baseball Stories
Although no longer the rivals they were when they were booked for Sacred Heart University’s 2011-2012 Student Affairs Lecture Series, Brian Cashman and Theo Epstein entertained a capacity crowd at the University’s Edgerton Center for the Performing Arts Tuesday night with tales of what goes on behind the scenes in the world of major league baseball. The event was moderated by ESPN’s Steve Berthiaume.
Cashman, senior vice president and general manager of the New York Yankees, and Epstein, general manager of the Boston Red Sox for nine seasons and now president of baseball operations for the Chicago Cubs, professed to have great respect for one another and to be looking forward to serious trade talk now that they aren’t arch enemies.
“Cash was always on top of everything. We couldn’t let our guard down; we could never relax,” Epstein said. “We tried to focus on executing our own strategy and building our organization the way we wanted to, but he seemed to be in all places at all times. I always felt like he was lurking around and had a great sense of the marketplace. It wasn't a good feeling, but I certainly admired those characteristics.”
Cashman said his perception of Epstein was “pure, objective discipline. Their decision making was based on pure, objective analysis about what was best for the team rather than emotion about the player. The Red Sox were constantly making the right choice instead of the popular choice. That helped us change our thinking and reset our buttons. The best compliment you can give is when you start studying your opponent, and I was forced to study what the Red Sox were doing.”
With the niceties out of the way, the two moved on to the Red Sox-Yankees rivalry, the rewards and frustrations of the job, the high and low moments of their careers and the funny things that happen behind the scenes.
Epstein said he grew up a Red Sox fan in the Boston area and had the hatred of the Yankees that goes along with that. “Once I was on the inside, I needed to shift my focus. I felt sometimes that we were focused on image rather than substance and were too focused on the Yankees. Of course we saw them 19 times a year for five-hour games, so we couldn’t ignore them. But, as an executive, I sometimes had to look away; as a fan, you can focus on the rivalry.”
“There was always a letdown after those series,” Cashman said. “It’s intense and the people you work for can overreact to what is essentially a three-game series.
They spoke of the stress that comes with making decisions under a public microscope. “There’s a winner’s curse in free agency. The real dynamic is that the moves that have the most acceptance from fans and the media are the one that don’t work out, because the bigger names command longer contracts and more money,” Epstein said.
“I seem to have buyer’s remorse after every move I make,” Cashman added. “When the players get resounding praise, it’s almost as if they can’t live up to the expectations.”
Cashman said the most disappointing moment in his career was the Yankees’ heartbreaking loss to the Diamondbacks in game seven of the 2001 World Series. His best moment was the World Series win against the Mets in 2000. “It was really important to Steinbrenner that we win. With him winning was ‘thank God we didn’t lose.’ There was a lot of pressure that year with our MSG television deal coming to an end. It felt like we had the whole corporation’s business plan on the line if we didn’t deliver. Thank God we did.”
For Epstein, the most disappointing moment was Aaron Boone’s homerun to keep the Red Sox out of the World Series in 2003. His proudest moment was winning the 2007 World Series. “The 2004 World Series win had the most relevance, because it had been such a long wait,” he said. “But in 2007, we had 12 homegrown players on team. When you win with 12 homegrown players, it resonates with so many people all through the organization.”
Cashman elaborated on his relationship with “The Boss,” noting that he never wanted to be general manager of the Yankees – and still doesn’t! “He was the boss of bosses. It was difficult because he did everything. He managed; he general managed; he did the tickets; he did the marketing. He micromanaged,” Cashman said. “We had some legendary fights; it was an interesting dynamic. But I learned so much from him. He was like a second father.”
The two swapped tales from the negotiating table with Cashman confessing to having dinner with Carl Crawford’s agent just to make the Red Sox think the Yankees were interested and drive up the price for the outfielder. Epstein countered with a story about booking all the rooms in the Nicaraguan hotel where Jose Contreras was staying when both teams were looking to sign him. The Yankees ended up signing Contreras, but Cashman admitted the maneuver got to Steinbrenner.
The two agree that signing players has become more difficult in the age of “Moneyball.” “It’s a tough environment to make trades. People are more conservative. Everyone has the same information, and they are evaluating players the same way,” Cashman said.
“The criticism is everywhere,” Epstein added. “It takes courage to make a risky move. You can’t be afraid to fail or you will never make a trade.”
During the question-and-answer session, the two were asked about dealing with aging superstars. “You have to have an alternative, but once you do, you tell them the truth. You have to keep the emotion out of it. You have to have that emotional disconnect,” Cashman said.
“It’s the hardest thing we deal with,” Epstein said. “That competitive drive that made them superstars also prevents them from being accurate self-evaluators.”
In response to a question about interleague play where American League pitchers have to take batting practice and step into the box during games, Cashman said simply, “I hate it.”
“I didn’t like it two months ago, but I like it now,” Epstein said to a laugh from the crowd. About his move to the National League, Epstein said he is looking forward to “a great, new challenge. My experience in Boston was so meaningful that I couldn’t just go anywhere. Because the Cubs haven’t won (since 1908) and have a great passionate fan base that deserves a winner, when we get it right, it will impact lots of generations of fans all over the country in a very unique way. I'm looking forward to working hard to get there.”
The SHU Baseball Team poses for a photo with Theo Epstein and Brian Cashman.