Why Theo Epstein and the Cubs felt now was the right time for transition
A few days after the Cubs were knocked out of the playoffs last month, Theo Epstein hopped on Zoom and conducted his standard end-of-season press conference.
In that conversation with Chicago media, Epstein talked a lot about his future and planted the seed for potential transition coming down the line. But he also reiterated that he was planning to remain in his role in the Cubs front office through the 2021 season — the final year of his contract.
Tuesday morning brought about the news that Epstein will be stepping down as president of baseball operations and leaving the organization effective Nov. 20 with Jed Hoyer sliding into that spot.
Epstein has long subscribed to the Bill Walsh school of thought that individuals should push themselves and find a new challenge after 10 years or so at one place. 2020 marked Epstein’s ninth season with the Cubs and he said he had been discussing a potential transition with chairman Tom Ricketts over the last few years.
So why did Epstein come to the decision to step down now, in mid-November, rather than finish out the final year of his contract?
Epstein expressed appreciation for how Ricketts handled the communication as the two sides figured out how to navigate the transition to ensure both the organization and Epstein would be in great spots.
“We’d been communicating and using October 2021 as a placeholder for when we would likely execute a transition,” Epstein said. “And this summer, it became apparent to me for a number of reasons that we should strongly consider moving up the date of the transition by a year. First of all, it became really clear that we’d be facing some significant long-term decisions this winter — decisions with long-term impacts. And those types of decisions are really best made by somebody who’s going to be here for a long time — not just for one more year — and somebody who’s invested in the organization for the long haul. Jed clearly is that person.
“Second, this summer it became clear the extent to which COVID was going to stress our business and our people and it’s affected every business in the sports world and really across the country generally. But due to those stresses, we were going to be facing a challenge of having to allocate some temporarily reduced resources in a way that would allow us to move forward and be successful and had I decided to come back in 2021, that would have made that challenge even more difficult.
“Last, Jed is ready to take over. He’s been a huge part of all of our success here. He’s been a huge part of my success and my career. … He really, truly does not need me over his shoulder this next year while we finish off a transition that — in a lot of respects – has been years in the making. So he’s gonna do an outstanding job. He deserves this opportunity and the Cubs are lucky to have him.”
From his perspective, Ricketts said, “the money had nothing to do” with the decision to move on now and Epstein clarified Ricketts never once brought up money throughout the conversations.
Epstein said he does not feel any burnout from the demands of the job or from working in baseball for nearly three decades. He is looking forward to taking some time away before beginning his “third chapter” in the game and enjoying baseball as a fan.
He also took a hard look at himself in the mirror and gained some clarity about why now might be the best time for this transition.
“I am self-aware enough to know that just based on my personality and the way I operate, forcing myself to change every so often is important,” Epstein said. “The Bill Walsh loose 10-year rule has always resonated with me and maybe it’s even particularly applicable to me. If you look at my track record in Boston and then here, in the first six years or so, we did some pretty epic things. And then the last couple years weren’t as impressive.
“Maybe what that tells me is I’m great at and really enjoy building and transformation and triumphing. Maybe I’m not as good and not as motivated by maintenance, so to speak. And as soon as you get to the point where it can start to feel that way to you, then I think you owe it to yourself and as importantly — if not more importantly — to your employer to be open about that and seek to pursue change that’s in the best interest in the organization and the individual.
“Not burnout, but I’m self-aware enough in this area to know that after a while, I need a new challenge. And I think the Cubs with everything that we’re facing and a natural transformation happening anyway with player group and coming through COVID and Jed being ready, it was the right time. And yeah, maybe I could have been useful in 2021, but Jed and I have been working on this transition for a long time and he is ready.”