Theo Epstein expects to be back in 2021, hints at major Cubs changes

The Cubs didn’t have the season anyone hoped for or expected, and President of Baseball Operations Theo Epstein acknowledged that in his annual end-of-season news conference.

The first question on everyone’s mind: Theo’s contract ends after 2021. What’s going to happen next year and beyond?

“Whenever that may happen.” Is that a hint Theo might want to stay beyond 2021? He’s said many times in the past that 10 years in one place is “enough,” but we don’t know if he’d like to continue past next year or not, and I think after that we still don’t know. There’s been a lot of speculation about Theo’s reported meeting with team Chairman Tom Ricketts later this week and that such a meeting might result in a buyout of Theo’s contract, but:

Too much reading between the lines, I’d say.

Now, on to the team. Like everyone else, Theo knows the Cubs offense failed in the postseason (and for much of the season), and that’s going to have to change:

This is something that I think some don’t take into account. Between the pandemic, which created uncertainty for everyone, the shortened season and the lack of fans in the parks, baseball in 2020 was far different than anyone expected and far different than anything we’ve seen before. He acknowledged things will have to change:

We have heard this before, as noted above (“similar to last year”), and we didn’t really see any changes in the “core group.” Since many of them are potential free agents after 2021, would it be worth one more season with them together, especially with the “uncertainty” Theo notes? Trading players like Kris Bryant or Kyle Schwarber coming off the bad years they had in 2020 would probably not produce the results in return that anyone wants. Further:

That applies to every team in baseball, not just the Cubs. While 162-game schedules have been released for 2021, no one knows whether fans will be allowed in ballparks next April, or if they are, how many will be permitted. The pandemic could still be going on by then, it could be ending, it could be worse than it is now. We just don’t know. Theo is right about “great uncertainty” for baseball — and then the sport has to deal with a potential lost season in 2022 due to a labor dispute.

A few other team notes:

Many of us have become enamored, for good reason, for the players that broke the Cubs’ World Series drought — perhaps too enamored, and I think Theo might have done so as well. No core group of players can stay together forever, and while it will be odd to see Bryant or Schwarber or Javier Baez or even Anthony Rizzo in another uniform, it could happen. (Rizzo, I suspect, will wind up staying, as he might get a contract extension that acknowledges his value as the face of the franchise.)

Regarding Jon Lester:

Theo and Lester have a relationship that goes back to 2002, when Theo took over the Red Sox just a few months after Lester was drafted by them in the second round. It’s that relationship, I believe, that got Lester to sign with the Cubs in the winter of 2014-15 when at least one other team (the Giants) had offered him more money. There is no doubt that Jon Lester is the best free-agent signing in Cubs history for his impact on the field and in the clubhouse. He is arguably the best free-agent signing in Chicago sports history. If the Cubs and Jon can agree on a price, I would not mind having him back for one more year. (They’ll obviously decline his option and pay him a $10 million buyout.)

And more about pitching:

This has been Theo’s biggest failure in his nine years here — developing strong starting pitching inside the organization. It’s possible, as he noted, that Adbert Alzolay could be exactly that. His last couple of outings in 2020 hinted at that possibility. But he’d be the only one in nine years. That’s not good enough. The suggestion is made in that tweet that getting “starting pitching depth from outside the organization” might involve trades of the core group.

So that’s where we stand in October 2020. I think it’s still possible that Theo decides he’d like to stay beyond 2020 and he and Tom Ricketts hammer out a deal for, I don’t know, maybe three or four more years. (It won’t happen this week, I’m certain of that.)

Lastly, if you are wondering why this news conference did not air live on the Cubs’ own TV channel, Marquee Sports Network, here’s why:

That is undoubtedly the reason, while these events are being held on Zoom. The team and league can’t control the feed, so they made the reasonable decision to not air them live.

Here’s hoping for a productive offseason and a better 2021 for the Chicago Cubs.