Well, it’s happening. It didn’t look like it was happening until next offseason, but we knew it was on its way eventually. Theo Epstein is leaving the Cubs.
The most broad thought I can offer on this is that it’s sad, most forcefully in the nostalgia sense and the what-might-have-been sense. Under Theo Epstein, and thanks to Theo Epstein, the Cubs had one of the best three-year stretches any team could ask for, from 2015’s plucky upstarts knocking off the Cardinals to 2016’s dominant, wire-to-wire leaders and yet tough-when-it-mattered young guns to 2017’s competent superpower nursing a 108-year hangover. But it didn’t last. It slipped. And when it did, there was no climb back. Theo Epstein’s Cubs tenure ended with three straight seasons that sat on the line between solid and fine. They’d feel different if there’d been postseason success, and a lot of that is luck, but at the same time, the postseason success in the three years prior also had something to do with luck. The more years one does this, the more the luck evens out.
Epstein was in Chicago for a lot of years. Nine full seasons. He leaves a well-stocked collection of personnel, a competent organization that, while it’s underachieved the last three years (especially the last two—2018’s Cubs did win 95 games), has the tools to contend at a moment’s notice.
But that’s not the expectation as Epstein leaves. The expectation is that a rebuild is coming. And it might hurt.
So, some collections of reflections as a good era, maybe the best era, ends:
Theo Epstein Was a Good Man for the Cubs
We don’t know what famous people are like in private, but it’s hard to remember a single time during Epstein’s nine years on the North Side that he did anything personally unsavory. He was classy and kind, and both a good leader and a good teammate in the public sphere. Yes, the record shows flaws: Addison Russell could have been handled differently (though even with that, it’s hard to say how exactly Russell should’ve been handled). But overall, Epstein made it easy to feel good about being a Cubs fan. And that’s worth noting.
Jed Hoyer Is the Closest Thing to Epstein
On this site, we’ve often referred to the Cubs’ front office as Epstein & Hoyer, viewing them as something of a cohesive unit. Hoyer’s worked with Epstein for a long time and has run the Cubs for a long time, indicating the organizational philosophy, in a baseball sense, will likely stay in Epstein’s mold.
Why Did Epstein Leave?
If we take the statement at face value, Epstein was never going to stay forever, and thought now was the best time to leave because he wanted Hoyer to be able to shape the rebuild as Hoyer saw fit, seeing as Hoyer would be the one to steer it once it was on its way. There’s no reason to doubt any of this, but it’s worth asking why Epstein was never going to stay forever. There’s a possibility that’s just who he is—someone who’s motivated by shorter-term projects and more diverse challenges, rather than someone who wants to stay in one job forever. It’s also possible Epstein was frustrated with the Cubs’ ownership, as the purse strings seemed to tighten over his last few years in the role.
Overall, our best guess is meaningless. We don’t know. It’s possible we never will. Epstein does seem like someone who isn’t motivated by the “lifer” kind of career approach, and if ownership was the problem, it’s hard to see why Hoyer would stick around, so as it stands, I lean towards this being less about ownership than just the natural progression of Epstein’s life. But that judgment’s up to everyone.
What Comes Next for the Cubs?
An implication here is that there’s a dramatic offseason ahead. Just yesterday, Javy Báez was being listed as potential trade bait (though Anthony Rizzo, to my knowledge, may remain the one untouchable Cub). We may see a lot of pieces move. Epstein may have not wanted to go through that. Hoyer might not want to go through that, but the Cubs seem to have arrived in the place where they feel they need to try something with the roster, so if there’s a market to move Báez or Bryant, or Contreras, or Schwarber, it appears none of those moves are off-limits. It’s unlikely there’ll be a full rebuild—a retooling seems more likely—but it shouldn’t be ruled out, and neither should a one-year reset like that of the Red Sox in 2012.
As far as the general manager role itself goes, with Hoyer promoted, don’t be surprised if it’s an internal promotion of Jason McLeod, who recently turned down the opportunity to interview with the Angels, perhaps thanks to a hint this was coming. But don’t be surprised by another hire, either, external or internal.
What Comes Next for Epstein?
One would imagine a very relaxing 2021. And good for him for that. Beyond there, though, he’s made it clear so far that he wants a “third chapter,” and he wants it in baseball. There’s speculation about the Mets and the Phillies, but the Mets seem to want to move right now as opposed to next offseason. It’s hard to hazard any sort of accurate guess, then, especially because there’s such uncertainty over where teams will stand once 2021 has played out, but it’s fair to wonder if Epstein wants something of a parallel situation to that of the Cubs, a team where: 1) Winning would be a significant accomplishment (as it was in Boston before Chicago), 2) The pocketbook isn’t especially tight, 3) Total control can be his. If I were setting odds, I’d still list the Mets and Phillies as the favorites (in that order), but I wouldn’t take either bet. I’d bet on the Tigers at reasonable odds. The Padres would’ve been intriguing a couple years ago, given Epstein’s roots with that franchise, but the Padres have gotten pretty good already. The Orioles are interesting, given Epstein’s deep cut (internship) roots with that franchise. Given he seems to enjoy being liked, at least to an extent, it’d be surprising to see him go to a direct rival of the Cubs, but such a move can’t be ruled out. And it is, of course, possible he’ll take more than one year off, waiting out the market (and potentially the virus).
Wherever he goes, the Cubs have been lucky to have him. The Cubs remain lucky to have had him. And the Cubs fans among us, myself included, are lucky too. Hopefully he gets the third chapter that he wants. If he does, what a three chapters it will have been. And how wonderful to have benefited from the second of the three.
