The Cubs have reached a critical junction this offseason. Much has been written regarding four core players entering their final season before becoming eligible for free agency. The same goes for three fifths of the Cubs 2020 entering free agency this offseason. With eight players in total set to enter free agency, lets take a look at what a 26-man roster will look for 2021 using only internal candidates. Pre-arb (italics) and arbitration (bold and italic) salaries are only estimates, and the Cubs will obviously not enter next season without making additions and subtractions from this roster, but it does give us a baseline to examine:

A look at the big picture helps clarify how little payroll the Cubs have committed long term. Only four veterans (Darvish, Heyward, Hendricks and Bote) are signed to guaranteed deals into the 2022 and beyond. Add in a handful of players who will be in their arbitration windows (Contreras, Happ, Caratini, Mills) and another handful still in their pre-arb years (Alzolay, Hoerner) who figure to stick around moving forward and the Cubs are only looking at about half of 26-man roster they have under their control for 2022.

Turning attention back to 2021 though, the first thing which jumps out at me is the potential non-tender candidates. The most obvious is Albert Almora Jr. His arbitration number is likely to come in north of 2M, which is far too much for a player who has finished each of the last two years in the Minors. You can subtract him from above and add him to the list of free agents. A possible outcome here is the Cubs simply give the money projected for Almora to Cameron Maybin instead. He’s coming off a 1.5M salary this season. If he would be willing to return on a similar deal the Cubs should strongly consider it.

Other potential non-tender candidates could include relievers Kyle Ryan, Ryan Tepera, and Dan Winkler. All three will likely see their salaries jump above 1M in arbitration. That figure is not egregious for any of them, but thinking in terms of roster flexibility none of those guys are late inning options at this point, and none of them can be optioned to the Minors next season. Does committing approximately 4-5M and three roster spots on middle relievers prudent? I’m on the fence, but I lean toward letting one of the two righties walk, and perhaps Ryan as well if the Cubs decide to re-sign Andrew Chafin or pursue an upgrade on the open market.

The final non-tender candidate would be Jose Martinez. As with the relievers, his estimated 3M salary is not bad if he recaptures his lefty mashing ways. He’s a limited player though, as a short side platoon DH and PH. I think it is a longshot they would walk away given they dealt two prospects for him at the deadline, but if they find teams offering potential upgrades when discussing trades early this offseason, a non-tender could be under consideration in those circumstances.

For now, I don’t want to dig too deep into potential trade and contract extension scenarios for the core players. There is going to be movement on that front one way or the other this offseason. At least one will be traded and at least one will sign. Potentially, I could even see two traded and two sign. Which ones or twos? I have my preferences, but without being privy to contract demands and how many teams are in the trade market for each player, I think spending too much time speculating is premature. We should have a clearer picture next month.

What I am more interested in at this point is if we hear about the team approaching Willson Contreras and Ian Happ with contract extensions. Now would be a logical time for the team to try to lock in both. Contreras matured as a defender this season and Happ matured at the plate. Given his athleticism Contreras is a good bet to hold up well behind the plate, even into his early-30s. Happ seems to be embracing a leadership role. With Jon Lester and Anthony Rizzo potentially leaving soon, they should look at securing the captain-in-waiting long term. While neither figures to be “the guy” moving forward, they can be important pieces as the team reshapes the roster for the future.