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Theo Epstein has been prepping the Chicago fanbase for the eventual breakup of their 2016 team for a couple of seasons now. The blockbuster hasn’t come, and most of the faces of that championship team remain. After a disappointing exit from the wild card round – they managed just one run over a two-game sweep at the hands of the Marlins – Epstein’s comments again suggest changes are coming for the Cubbies.

Nine players remain on the roster from their World Series winner, and while that may not seem like a lot, it does constitute roughly 35% of a 26-man roster. Kris Bryant, Anthony Rizzo, Javier Baez, Willson Contreras, Albert Almora, Jon Lester, Kyle Hendricks, Jason Heyward, and Kyle Schwarber represent the longest-tenured group of Chicago players. Technically, manager David Ross can count as a 10th member of their title team still hanging around the clubhouse. Ian Happ and Victor Caratini didn’t debut until 2017. Jose Quintana joined the team at the 2017 deadline. Yu Darvish signed as a free agent prior to the 2018 season.

The pillars of this Cubs’ run will dwindle further in the coming years. Architect Theo Epstein is likely to depart after next season. Lester is a free agent this winter. Almora seems to be out of chances and in need of a change of scenery. Odds favor Heyward or Hendricks to be the “last man standing” as they both have contracts that should keep them in Wrigley through 2023. Rizzo, Bryant, Baez, and Schwarber are each entering the final year of their contracts – assuming the Cubs pick up Rizzo’s $16.5MM option.

Epstein spoke about the latter group, providing typically candid analysis of not only the Cubs foursome, but more broadly about the value of one-year contracts. Per the Athletic’s Sahadev Sharma, Epstein said:

I think there are going to be certain fundamentals that are true of this winter and of this market that have been true for decades. One of those is especially relevant in our situation, a one-year deal for a really talented player is a valuable thing. That’s to our benefit both to what we can do in constructing the 2021 team and having an additional year of control on certain players and also potentially to our benefit in the trade market as we look to make some changes. I think that’s a fundamental.”

Essentially, it sounds as if Epstein’s offering a ’fear not’ for those who think the Cubs have waited too long to return anything of value for the final year of Bryant, Rizzo, Baez, and/or Schwarber. To Epstein’s point, players on one-year deals are often devalued in the public square, but there’s a lot that can be extracted from a full year. Further, the flexibility a one-year deal affords shouldn’t be discounted – perhaps especially in our current climate. The fear of losing talent to free agency is understandable, but the more difficult gaff to overcome is the presence of “the albatross,” a highly-paid player on a long-term deal who no longer contributes on the diamond. Baez’s confounding 2020 is a testament to the swings that even talented players can experience year-over-year.

The trouble for Epstein is that Chicago’s current roster is flush with semi-expensive players on short-term deals who are coming off disappointing seasons. But to Epstein’s point – those players are still valuable. Whether the Cubs keep them or trade them, there’s always an opportunity cost. Said Epstein, per Sahadev:

There’s always a trade-off of being transactional and taking some of those players away from the current group and solidifying the future. There are trade-offs and balances that you have to be mindful of. The math simply changes as you get to a point where a lot of your best players only have one year left. It becomes less appealing to continue to invest opportunity cost in simply the present.”

Epstein has hit on a similar refrain in each of the last couple of years, and some changes have been made. They hired David Ross as the manager, they refrained from big-money free agent deals since signing Darvish (with the exception of Craig Kimbrel, who has only one more guaranteed season left on his deal), and they poured considerable energy into exploring trade options and/or extensions for their stars – but they haven’t made any of those deals.

Therein lies the rub for Epstein and GM Jed Hoyer. After years of exploring their options and walking the difficult path to try and sustain contention, they’re running out of time to pull off one of those – in Epstein’s words – “impactful, significant moves.” Whether or not they’re able to consummate that brand of deal this winter may depend on whether the 29 other GMs agree with Epstein about the value of talented players one-year deals.

Of course, Mookie Betts represents the most recent superstar player to be dealt on a one-year deal, and Indians’ shortstop Francisco Lindor is among those players who could be available this winter. Both players are probably more valuable in a vacuum than any of the Cubs’ foursome. Still, the Betts deal is instructive in so far as it necessitated the Red Sox’ willingness to take a step back, even though they received a major league regular as part of their return. The Cubs also have the option of packaging a couple players in the same deal, something he’s done in the past to extract additional prospect value..

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