"Obviously, being there for 10 years, there's a connection and it will never go away," said Epstein, who grew up two miles from Fenway Park. "I don't feel like it's my team, so to speak, but I do root for a lot of people there."
While Epstein's tenure in Boston was largely successful -- highlighted by the club's first two World Series titles since 1918 during his tenure as general manager -- it ended with infamy. The 2011 Red Sox became the first team in Major League history to own a nine-game lead in September and miss the postseason.
"I think everyone moves on," Epstein said. "I remember stuff from 2003. I'll sit there and see Aaron Boone coming to the plate sometimes. Every time you have the opportunity to advance and do some damage in the postseason and get to the postseason, and you don't, that always stays with you -- last September in particular, because we not only failed to perform in the standings, but we lost our identity as a team.
"That was a tough pill to swallow. I think for everyone involved, it stayed with them. But at the same time, you move on and learn from it, and try to get better. I take responsibility for the team not getting to where we were supposed to go. But I think a lot of the people involved took responsibility and have moved on."
The fundamental things Epstein is trying to change with the Cubs are very similar to when he took over as GM of the Red Sox before the 2003 season.
The difference, however, is that the Red Sox were built to win when he started, led by established stars like Pedro Martinez, Manny Ramirez and Nomar Garciaparra.
At 21-42, the Cubs entered Friday's game with the worst record in the Major Leagues.
"We made moves at the big league level and had some success right off the bat, and that bought us time to commit to the Red Sox way of doing things, which we established there in scouting and player development," Epstein said. "The work is similar here, but there was clearly a mandate for change."