In addition to Epstein, a source told ESPNBoston.com that San Diego Padres general manager Jed Hoyer will leave for the same position in Chicago. Hoyer had previously worked as an assistant to Epstein in Boston.
The front office shakeup will have a direct impact on Dempster. The 14-year veteran has a one-year, $14 million player option to determine if he will remain with the club for the 2012 season.
He said he plans to discuss the blueprint for success with the new front office regime before making a decision.
"You know what's funny is people sit there and you see the kind of money that it is and automatically you just assume that it's a no-brainer," Dempster said. "And to me, I never played the game for money. I never do. It's a great byproduct of what we do, but I play to go out there and try and win, and win as a team. I don't know what the direction of the team is with somebody (new) in charge. ... Do they want to go younger? Do they want to go older? Those are questions that obviously I gotta ask.
"But I love playing in Chicago. I love being a Chicago Cub, and I want to be here for the rest of my career. I'm happy that Theo is going to be in charge now and really looking forward and excited and getting an opportunity talk with him. And hopefully it's not just picking up an option for this year, but I'll go out there and play the best I can and be here for a long time."
Dempster is coming off a somewhat disappointing 2011 campaign in which he posted a 4.80 ERA and 10-14 record. Those numbers were weighed down by an uncharacteristically slow start -- he posted a 9.58 ERA in six April starts.
Dempster didn't mince words when discussing his performance last season.
"You want my honest answer? I thought (his 2011 season) was terrible. ... April was the worst month of my career," Dempster said. "For some reason or another, I just found a way to give up four or five runs every game. I scratched and clawed the whole way to try and make it respectable at the end of the year, but I think that was a big reason why we didn't succeed the way we did. I mean, obviously, we had guys out, but your team starts with your starting pitching. I just had a subpar year and I'm gonna go out there and bust my tail this winter. And I'm gonna ... do the best I can to go out there and have a better year next year. "