Editors note: The following post is a midwinter dispatch from Dylan Stableford of Yahoo! News
FAIRFIELD, Conn. — "I never wanted to be the general manager of the New York Yankees," Brian Cashman said. "I still don't."
You would think he was joking, but he said it twice.
Cashman and Theo Epstein, his former Red Sox rival-cum-Cubs president, took part in a wide-ranging, surprisingly candid discussion with ESPN's Steve Berthiaume on the campus of Sacred Heart University in Fairfield, Connecticut on Tuesday.
Theo and Cash, as they call each other now, have not seen Moneyball.
"We live it," Epstein said.
But they have enough stories for a sequel.
Cashman recounted his contentious relationship with George Steinbrenner. "We had some legendary fights," Cashman recalled, calling the late Yankees owner "intense" and "the boss of all bosses."
"Forget the game, every inning was Armageddon," Cashman said. "It was very tough to operate like that in a game of chance like baseball."
The Yankees GMs that had preceded him— including Bob Watson and Bob Quinn — were worried about their health. And he understood why: "The jubilation from the winning was, 'Thank God we didn't lose.'"
The most striking example of that dynamic came during the 2000 Subway Series against the Mets, when Steinbrenner was concerned that the Yankees' television contract with MSG hinged on the outcome. "It felt like if we lost, we'd lose the city," Cashman said. "The entire corporate business plan was on the line."
At one point during a Q+A with the audience, a brash youngster asked Cashman bluntly, "Do you feel comfortable with A.J. Burnett in the starting rotation?"
"You sound like George," Cashman quipped.
Losing was not tolerated off the field, either — especially when it came to free agents coveted by Epstein, like, say, Jose Contreras.
In 2002, Boston's Latin American scout was the first to arrive at a Nicaraguan hotel where Contreras — who had defected from the Cuban national team--was staying, and booked the room next to the right-hander.
"He called me up and said, 'All the other teams are on their way down here, what do you want me to do?' I said, 'Buy all the rooms,'" Epstein recalled. He did, and Yankees executives were forced to stay down the road. "We were smoking cigars and drinking rum [with Contreras] at four in the morning."
"The boss was not happy," Cashman recalled of Epstein's stunt. "He would not be denied."
The next day, Epstein said, the Yankees offered him $10 million more.
"That was it," Epstein said, adding that he confronted Contreras in the tunnel at Yankees Stadium years later. "I said, 'What happened?' He said, 'I don't know.'"
Another pitcher both executives coveted was Curt Schilling. In Nov. 2003, Epstein flew to Arizona to negotiate a contract with Schilling, spending Thanksgiving with the family. Schilling's wife cooked her first Thanksgiving turkey. Jed Hoyer, Epstein's assistant GM, got food poisoning.
"He was vomiting all over the place," Epstein said. "I was throwing $20 bills all over the hotel room for the maid because I felt so bad."
When Epstein finally reached a deal with Schilling, he said he walked into Schilling's home office to type up the contract. Sitting on the desk, a copy of "Negotiating For Dummies."
"He had been using it the whole time," Epstein said.
The new Cubs president bemoaned the rise of Moneyball-style management, because until the book became a New York Times bestseller, only a handful of teams were able to truly assess the market.
"Owner of baseball teams have a lot of leisure time because they're really rich," Epstein said. "So they're on their yachts, reading 'Moneyball,' saying, 'Hey, why aren't we doing this?'"
The unlikely chummy GMs revealed only once did they even discuss a trade, when Epstein, then in his first year in Boston, offered Shea Hillenbrand for Nick Johnson.
"Cash laughed at me," Epstein said.