Theo Epstein expects to be with Cubs in 2021, seems poised to leave after that

"You have to be smart in discussing the timing and nature of a transition," Epstein says.

(670 The Score) Judging by Cubs president of baseball operations Theo Epstein’s own words, he seems poised to leave the organization when his contract ends after the 2021 season.

Two days after a report surfaced that he could part ways with the Cubs before his contract ends, Epstein on Monday pushed back at that line of thinking while also seeming to hint that his exit will come when his deal is up.

“My expectation is that I’ll be here,” Epstein said in regards to the 2021 season. “And my expectation is also that I’m going to do whatever is best for the Cubs every day. That means being thoughtful about a transition, whenever that may come. But I’m focused on the 2021 Cubs and how to position ourselves for long-term success.”

Epstein and Cubs chairman Tom Ricketts are scheduled to meet this week to discuss Epstein’s future with the organization, David Kaplan of NBC Sports reported Saturday. The expectation is Epstein won’t sign a third contract, and he could leave the organization before the end of his contract if the sides agree that’s best for the Cubs, Kaplan reported.

When he was hired by the Cubs in October 2011, Epstein cited the benefit of executives and organizations experiencing change every 10 years or so at the top of a baseball operations department. He stood by those words Monday, an indication that he’ll likely leave the Cubs after the 2021 season.

“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. “As part of that process, I usually meet with Tom one-on-one as well. Those are meetings that we’re looking forward to having. We were hoping to do it quietly and behind the scenes. We’ll still do it as quietly as possible. That was the thrust of the article, essentially that we’re going to meet. We do do that every year.

"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). I think I mentioned it my first day as a Cub and again when I signed my second contract. I’m not going to run away from those feelings, but I also am as invested in the Chicago Cubs as our leader in baseball operations today as I was at any point in the last nine years. I woke up this morning thinking about how we can improve for next year and position ourselves for long-term success. 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.”

The Cubs were swept by the Marlins in two games in the best-of-three wild-card round after going 34-26 and winning the NL Central. The Cubs won the World Series in 2016 and have advanced to the NL Championship Series on three occasions in Epstein’s tenure, which dates back to October 2011, but they’ve either exited in the wild-card round or missed the playoffs altogether in each of the past three seasons.