The Chicago Cubs season ended in a disappointing fashion last week, as the underdog Miami Marlins swept them out of the Wild Card round. Chicago had a fine season, making the playoffs for the fifth time in the last six years and taking home their third NL Central division crown during that span.

Looking at the future of the Cubs organization, there is some questions about who will be leading the franchise moving forward. Theo Epstein will be entering the final year of his second contract as the President of Baseball Operations and is not expected to sign a third.

Speaking with the local radio station of 670 The Score, Epstein talked about his role with the team moving forward, saying that he expects to return in 2021. While he pledged to continue to position the Cubs for long-term success, Epstein did insinuate this to be a transition period which could leave him on the job market after next season.

Epstein will be meeting with the team owner and chairman Tom Ricketts this week, but Epstein described this as an annual occurrence, in which they will discuss the future of the Cubs.

“After every season, we get together as leadership – baseball ops leadership and ownership – and we talk about the state of the club, the state of the organization, what lies ahead in the future, how to improve going forward, how to position ourselves for long-term success,” Epstein said.

Epstein has put together a Hall of Fame career as an executive, as helped end two of baseball’s the infamous “curses” winning World Series’ with both the Boston Red Sox and the Chicago Cubs. He first took over as the Red Sox GM in 2002, becoming the youngest to ever hold that position in MLB history. Epstein ran the Red Sox from 2002 through 2011, winning two World Series championships.

After that 10-year span, Epstein left Boston and took on the challenge of winning with the Chicago Cubs. Epstein has always believed in the notion that leadership can grow stale over time and cited this again as he enters the final year of his decade running the Cubs.

“Look, I’ve been transparent about my feeling that after a certain period of time, there can be real benefit both for an individual leader and for the organization for change. I’ve not backed away (from that thought).” Epstein explain.

“But given the things I’m on record with about the benefits of change at a certain point, it just means that you have to be smart in discussing the timing and nature of a transition. Because it’s inevitable at some point.”

One of the interesting aspects of Epstein’s departure is what happens with Cubs GM Jed Hoyer. Hoyer could take over as the new President of Baseball Operation, but he has worked under Epstein dating back to 2002, when he was his assistant GM in Boston.

This will be an interesting story to watch develop, as the Cubs have a lot of decisions to make if they want to remain perennial contenders moving forward.