The short version: Epstein really likes what Boston's president of baseball operations, Dave Dombrowski, has done.
"They're well positioned. A lot of good young players," Epstein said of a group that includes many youngsters who came to the organization during his tenure -- Xander Bogaerts, Mookie Betts, Blake Swihart, Jackie Bradley Jr. , Henry Owens, Christian Vazquez and Matt Barnes. "They've added a couple of really good pitchers this winter, so it should be a fun year for them in the American League."
Epstein himself was after one of those pitchers, David Price, with the Cubs reportedly offering the left-handed ace about $50 million less than the Red Sox. Price agreed to come to Boston for $217 million over seven years.
"Price is a great pitcher. One of the best in the game," Epstein said. "I came to admire him over the years, watching him pitch against us, so I wish him the best and the Red Sox the best. I think it'll be a great fit."
Another player Epstein brought to Boston, David Ortiz, has said 2016 will be his final season. Epstein noted that it was "kind of sad" that it'll be the end for Ortiz, but at least the player is going out on his own terms.
Ortiz is still one of the best hitters in baseball, Epstein said.
"He's going to be a force for good, whatever role he has in life," Epstein said. "I hope he has a great year and can go out on top. He deserves it."
And then there is the matter of Manny Ramirez, who works for the Cubs as a hitting adviser. With the recent announcement of the Hall of Fame's 2016 class, there has already been chatter for 2017 about Ramirez, with his 555 home runs and .312/.411/.585 slash line and two positive PED tests.
"Manny's turned his life around," Epstein said. "He works for us in Chicago. He's great with our young hitters. Teaches the kids not to make the same mistakes he made. He's really just trying to make a positive impact on the game that gave him so much and trying to help young players.
"If that has any influence on his [Hall of Fame] candidacy, then good for him. I know it's coming from a genuine place. He's made his mistakes over the years, but he's doing a lot of good now."