REPORT: Theo Epstein and Tom Ricketts to Discuss Cubs Future, Including Transition Plans as Soon As This Offseason

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REPORT: Theo Epstein and Tom Ricketts to Discuss Cubs Future, Including Transition Plans as Soon As This Offseason

Chicago Cubs

If we already know that Chicago Cubs President of Baseball Operations Theo Epstein is unlikely to return to the Cubs after 2021, his final year under contract, shouldn’t transition planning begin very soon?

Moreover, since proper organizational administration takes place over a much longer horizon than a single season, wouldn’t it be ideal if the Cubs organization was working through the transition during the 2021 calendar year so that whatever medium and long-term plans are deemed best for the organization can be executed, in tandem, by the current front office and whatever front office comes next? After all, it’s a rare circumstance where you know this far in advance that a change is coming.

So, then, I’m actually pretty encouraged to hear – on the day after the Cubs were eliminated from the 2020 postseason – there are already plans in place for Cubs Owner and Chairman Tom Ricketts to have these conversations with Epstein.

The latest from Dave Kaplan at NBC, which includes quotes from Ricketts, indicates that the two men will meet next week to discuss the long-term plans for the organization, and both are more interested in the long-term success and health of the Cubs than merely figuring out how to handle a short-term transition, if and when one arrives. Specifically, Kaplan’s sources indicate, “Ricketts and Epstein have a great relationship and will collaborate on planning a transition that is in the Cubs’ best interests. The two options that will be discussed include Epstein staying through the end of next season and helping transition the organization to a new team president. Or, Epstein exiting now and the club hiring a new head of baseball operations.”

I expect that last part there will come as a shock to many, and it’s important not to read that as “Epstein might get fired.” I truly don’t believe that’s the kind of relationship Epstein and Ricketts have. Instead, it’s merely an option on the table: if they decide together that it would be better to seek a new front office structure right away, they might do that. But given that Epstein is on a hefty contract through next year (reportedly $10 million for 2021), and given that a really good transition process might take a year, I think it’s far more likely that Epstein is around through 2021. Kaplan indicates that is more likely, as well.

I expect we’ll hear more about this on Monday when Epstein holds his end-of-season presser, though I’m not sure how specific he’ll be. You also have to keep in mind that Epstein’s lieutenant, Jed Hoyer, would be strongly in consideration to simply slide on up to the President’s seat, and if Epstein wants to see that happen, there will probably be some negotiations behind the scenes, in the coming weeks or months. That, too, might limit what anyone can say.

This isn’t really a “lame duck” situation. It doesn’t project to be a situation where Epstein is just playing out the string, with each side unhappy about a looming separation. Instead, this is an opportunity for the organization – which is bigger than Epstein – to be very proactive to ensure a long-term continuation of The Cubs Way (so to speak), and more importantly, the big steps the Cubs have finally started to take to improve their player development infrastructure.

With a roster that will necessarily be massively different after next year – if not sooner – it’s all the more important, in my view, to have some of those transitional voices in place before the end of next season. Ideally, they’d play a part in what happens this offseason for the Cubs. If the next top voice is to be Hoyer’s, well, that’s easy enough. But even in that case, you’re going to want to bring in a new GM, and possibly some other external voices to move on to the next phase. Can you hire a GM a year in advance? Or a new President a year in advance (if the gig isn’t going to Hoyer)? It’s not really something that is done; I’m just saying, it sure would be nice to see the Cubs pull it off if it’s indeed already true that Epstein is leaving after 2021.

Stay tuned. Even if Epstein isn’t leaving this offseason, it nevertheless figures to be a very important time in the Cubs’ front office. The new culture Epstein helped create, to say nothing of the 2016 championship and multiple playoff runs, leaves plenty that we want to see continue long into the future. Let’s not forget where things were before Epstein and Co. took over in December 2011.

To that end, a reminder: Virtually all of us have been operating under the assumption that Epstein is gone after next year. Not necessarily because he’s unhappy or the money isn’t there or whatever; but instead it’s because (1) he has, himself, said that 10 years in one spot is about the right length of time (next year is his 10th year), (2) his contract is up and he’s currently making top-of-the-market money, and (3) the core he helped build is pretty much all up after next year also. The time for a transition is just going to make too much sense, and since we already know it’s happening, those conversations absolutely should begin as soon as the 2020 season ended. So, they will.

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Author: Brett Taylor

Brett Taylor is the Editor and Lead Cubs Writer at Bleacher Nation, and you can find him on Twitter at @BleacherNation and @Brett_A_Taylor.