"It wasn't a last-minute decision. It was something I had talked about all year long," Epstein said on the show. "Ben Cherington and I had talked about it for years. We had so many lunches where I'd just take him out and say you're the guy I want to take over. There's a very good chance that the end is coming for me, it's gonna be 10 years with the Red Sox. We talked about his development and all the different things he had done in the game. But the one or two areas where he still needed some development time, in the last two or three years, we specifically got him a lot of experience in those areas so he would be well-rounded to take over."
Epstein was asked about leaving while still under contract.
"It's the standard in baseball that employees who are offered promotions are almost universally allowed to leave," Epstein said. "This became a huge deal but it didn't have to be.
"When the Cubs became a possibility I was open about the fact that was probably the only place I could really see myself. After working for the Red Sox, you can't just go anywhere but the Cubs. Because of the similarities between the franchises and the fact that they haven't won in 103 years. And the fact that that's such a great challenge. That was kind of the one place I could see myself. So when they offered the promotion, it was fairly standard."
Asked about the possibility of signing Manny Ramirez, Epstein said "I don't think it's a good fit for us."