AnalysisNL Central

Offseason Outlook: Chicago Cubs

All offseason, Diamond Digest writers will be taking a look at each team’s 2020 season and looking forward at what moves each team might have to make to set themselves up for improvement in 2021. Today, Ryan Ruhde takes a look at the Cubs! 

It’s difficult sometimes to come up with new words to talk about the Cubs at this point. Of so many teams in baseball, the Cubs are in one of the most notorious crossroads, with this being one of the worst outcomes imaginable if you were in 2016 to attempt to predict what the Cubs would look like after the 2020 season. Surely there’s a lot of bright spots on the roster, and yet I struggle to look at the Cubs as currently constructed and see an avenue to postseason success in 2021. While it’s difficult to complain about six consecutive years of competitive Cubs baseball, there hasn’t been a single postseason win to celebrate in the last three of those years. The team could very easily look almost identical next season, but with the departure of Theo Epstein and rumors swirling vigorously around the team, that’s difficult to bet on at this point. Here’s how the team looks now.

2020 Season in Review

2020 Record: 34-26, 1st Place in NL Central

Team MVP: Yu Darvish

Team Cy Young: Yu Darvish

Biggest Positive Surprise: Ian Happ and Jason Heyward

Biggest Negative Surprise: Kris Bryant, Anthony Rizzo, Javier Baez, Kyle Schwarber

First of all, it’s important to note that 2020 was undeniably a success for the Cubs, with the team capturing its third division title in five years and first since 2017. One of the biggest contrasts with the Cubs of 2018 and 2019 was the pitching, and no man was more representative of that than the team’s best pitcher and player overall, Yu Darvish. Darvish was phenomenal in 2020, pitching to a second-place finish in NL Cy Young voting with a 2.01 ERA and continuing the excellence that began in the second half of the 2019 season. Darvish became the ace that he was signed to be, allowing no more than four runs in every single game he pitched and allowing just four runs through the entire month of August.

Two other crucial positives to the team were the lifeblood of the team’s outfield, which took a turn for the better in 2020 with Ian Happ having an excellent month of August and Jason Heyward posting his most successful season in a Cubs uniform. This wasn’t necessarily a surprise, as the two had the potential to break out in the 2020 season, but it was absolutely reassuring to see their success manifest, especially amidst the struggles of so many other players on the roster. Happ was the team’s most valuable position player with 1.9 fWAR, with Heyward not far behind at 1.8. These two anchored the offense, especially in the month of August, and will continue to be important to the team in 2021 regardless of the roster around them. 

Here’s where things get murkier, with the four players whom I listed as negative surprises being the four most consequential players for the team’s direction currently. Their struggles in 2020 were somewhat confounding, with four of the team’s most important role players all struggling to get anything going offensively. Rizzo had the highest wRC+ of the bunch with a mark of 103, and Baez managed just a 57 wRC+ on the year. The kicker, though, is that all four of these players are set to be unrestricted free agents upon the conclusion of next season, and it’s incredibly difficult to evaluate any of them at this point. It’s hard to say much more about any of them, but it’s only possible to blame offensive failure on injuries, inconsistency, and rule changes regarding in-game video for so long. 

2020-2021 Offseason Preview

Offseason Overview

Key Losses: Jon Lester, Jose Quintana, Tyler Chatwood, Jeremy Jeffress, Cameron Maybin, Jason Kipnis

Areas of Greatest Need: Starting Pitching, Relief Pitching

Indications out of Wrigley Field so far are that the Cubs are expecting to have “significant roster turnover” before we see the team take the field again in 2021. There’s a lot that that could mean, but more than anything else it means that the team will almost certainly change much more in the coming offseason than it has in any single offseason since 2015-16.

The Cubs are losing ⅗ of their hypothetical 2020 starting rotation to free agency in addition to their most trusted reliever, so it’s no surprise that pitching is the team’s greatest need across the board. The losses of Lester and Quintana mean that the rotation will look very different after the two lefties, especially Lester, have been mainstays for years. In all likelihood, a bit of a shakeup for the rotation won’t be a bad thing, with Lester reaching the end of his career and Quintana never quite pitching at the same level as he did on the south side of town. The only pitcher of the three starters that I would expect the Cubs to be interested in bringing back is Chatwood, who had two of the best starts of his career early in the 2020 season before injuries kept him off the mound for most of the season.

Jeffress, Maybin, and Kipnis are the team’s most recent supplemental signings meant to bolster the position player core, and Jeffress especially was successful in that role in 2020. As I mentioned above, he was David Ross’s most trusted reliever this season, and in that regard, he was very valuable as the bullpen worked towards the consistency that it developed towards the end of the season. Maybin and Kipnis were not really everyday players or the focus of the roster, but Kipnis was a fairly dependable hitter and Maybin provided some good defense. Ultimately neither will be the focus of the offseason, but it’s certainly not too difficult to see either one back in a Cubs uniform next season on a minor league contract.

Offseason Wishlist

Free Agency

Big Name Targets: Marcell Ozuna, DJ LeMahieu

Realistic Targets: Jake Odorizzi, Tyler Chatwood, James Paxton, Brett Anderson, Chris Archer, Michael Wacha, Jeremy Jeffress, Carl Edwards Jr., Jurickson Profar, Hunter Renfroe, Jason Kipnis

I’m going to start with this: with all indications being that the Cubs will not be dedicating all of their energy to contending for a championship in 2021, even with several large contracts coming off the books they very likely won’t be big players in free agency this year. There will very likely be a bidding war for each of George Springer, Trevor Bauer, and JT Realmuto, and the Cubs have no reason to pursue any of these players heavily even if they could hypothetically afford them. Ozuna and LeMahieu shouldn’t be any different, but the Cubs should at least be more open to signing either of them, as they may come at a good price considering their performance, and LeMahieu would help lock down an infield with production that is far from guaranteed in the years to come.

Still, don’t expect either of them to be a Cub next season, either. If the Cubs do make any notable free-agent signings in the coming months, they should be players that the team can hope will serve as valuable players in 2022 and beyond. This is where the next tier of guys I listed comes in, those who could realistically be expected to produce well for the Cubs but won’t come at the exorbitant prices of the top tier free agents. 

Most of them (the first six) are starting pitchers, largely because the Cubs have three rotation spots that are not guaranteed in the years to come, and they would be wise to have as many options to fill those spots in 2022 as possible. These guys should cost no more than $10-12 million per year each (Paxton/Odorizzi), but most of them will cost well under $10 million and are a reasonable gamble at that price. As I mentioned before, Chatwood is a very reasonable expected signing out of this group, as the Cubs are clearly high on his potential and he did begin to find success early in 2020. If they agree on a reasonable price, which would be well below his salary over the last three years, he would very likely be welcomed back by Jed Hoyer’s front office. 

The remaining four would also be bets on potential, with the most notable name in the mix for Cubs fans being Edwards. The team traded him away in 2019 for reliever Brad Wieck, and he has since been with the Padres and Mariners before being DFAd by the Mariners in 2020. Edwards is going to sign somewhere on a minor league contract, and while he likely needed the change of scenery when the Cubs traded him last year, the team has a formidable pitching lab and would be wise to dedicate a very small contract to what Edwards has the potential to be. His potential likely isn’t as high as it was when he was a top 50 prospect in baseball, but there’s no reason not to bet on Edwards, especially when he’s already familiar with the organization. 

In addition, the Cubs will likely be interested in bringing Jeffress back once again, and he should be interested in a return after finding success with the team this season. Profar and Renfroe are both former top prospects who are almost guaranteed not to be stars but will certainly be worth the contracts that they receive, and the Cubs should be in line in hopes to be the team that can provide either of those contracts. Finally, signing Kipnis again would take no more than a minor league contract, and he’s a generally well-regarded veteran who will help fill out a roster that will be in flux.


The Cubs are arguably the single most important team in the MLB trade market this winter, and that is both a valuable and dreadful position in which to be. The team has five big name players that could very easily be dealt this offseason: Baez, Bryant, Darvish, Kyle Hendricks, and Schwarber. Those are far from the only names that are available, as well. The unfortunate reality is that Darvish and Hendricks, who are both under contract for three more years and who both were the most valuable players on the 2020 team, are easily the team’s most valuable trade assets. This means that, yes, if the Cubs are serious about getting value in return for the players they deal this offseason, one of Darvish or Hendricks will very likely need to go. 

The player that is probably the most likely to get traded is Kris Bryant, whom the Cubs are likely already working hard to move before the deadline to tender contracts to players in their first six years of team control. I would also expect Schwarber, whom the Cubs have held onto tightly thus far but who has underwhelmed expectations, to be on his way out. Beyond those two it’s difficult to tell what the team will do, but here are a couple of options which seem among the more likely that the team will consider.

Trade 1: Kris Bryant to the Nationals for IF Carter Kieboom and at least one pitching prospect

A trade centering around Bryant and Kieboom seems to make sense for both the Nats and the Cubs, but this assumes both that 1) The Nationals are looking to stay competitive in 2021 and 2) The Nationals intend to sign Bryant to a contract extension after trading for him. I think that this feels like a bit of a stretch, but the fit is surely there: The Nationals get Bryant, an established star, to fill a major hole at third base while the Cubs get Kieboom, a former top 20 prospect in baseball who has struggled massively, in hopes of filling his spot in the longer term. All of the Nationals’ top ten prospects right now are pitchers, and the Cubs would likely attempt to work at least one of them into the deal as well. Another large concern here is that whether Bryant remains an established star is questionable, and he very likely won’t get quite the haul in return that many Cubs fans might hope for. 

Other teams that will likely be in the mix for Bryant: Twins, White Sox, Athletics, the entire NL East (no, really).

Trade 2: Yu Darvish to the Angels for OF Jordyn Adams, RHP Chris Rodriguez, RHP Jose Soriano

Darvish is a pitcher that would make a ton of sense for the Angels, coming on a contract that is cheaper than that which he may command were he a current free agent. Still, he’s owed just shy of $60M over the next three seasons, which is no small commitment. The Cubs would likely have Brandon Marsh in mind as the headliner of a return for Darvish, but that would require the Cubs to pay at least some of Darvish’s remaining contract. If they weren’t to eat any of Darvish’s contract, Adams is also a solid prospect, and the Angels would likely have to supplement the return with at least one pitching prospect either way. This is one of many deals that the Cubs would consider for Darvish, and almost any team would be interested in three years of one of baseball’s most dominant pitchers. Still, age is a factor for Darvish as well, as he’ll be 37 when his contract expires after 2023.

2021 Projected Roster

Projected Lineup: 

1) Ian Happ, CF

2) Anthony Rizzo, 1B

3) Javier Baez, SS

4) Willson Contreras, C

5) Jason Heyward, RF

6) Carter Kieboom, 3B

7) Nico Hoerner, 2B

8) Jurickson Profar, LF

9) Pitcher (Victor Caratini, DH)

Projected Rotation:

1) Yu Darvish

2) Kyle Hendricks

3) Tyler Chatwood

4) Alec Mills

5) Adbert Alzolay

Projected Bullpen: 

  • Craig Kimbrel
  • Jeremy Jeffress
  • Rowan Wick
  • Ryan Tepera
  • Jason Adam
  • Kyle Ryan
  • Brad Wieck
  • Dan Winkler

I can’t say that trying to predict the aforementioned significant roster turnover was easy, but attempting to predict the roster itself was far more difficult after I hardly identified any specific moves the team would make in the coming offseason. I assumed that the team would deal Bryant and Schwarber, re-sign Chatwood and Jeffress, sign Profar, and otherwise keep the roster largely the same. Ultimately I’m not sure that I would call this roster significantly different from the Cubs that we saw in 2020, but it is certainly different in a couple of important ways and has the potential to be a very good team that may still capture a division title in what is now the weakest division in baseball.

This roster would involve filling several holes, notably in the rotation, with internal options, which is not an easy task for any team that isn’t the Dodgers, Yankees, or Rays at the moment, but there are several bright spots here, and I would be ashamed if I never mentioned Adbert Alzolay. The former top prospect has dealt with injuries in recent years but showed off a new slider in 2019 that looked phenomenal, and he was one of the team’s more successful pitchers this season. He will be leaned on rather heavily in 2021 if the team does find any success, but he has shown that he may yet be quite capable of succeeding in such a role.

Ultimately this Cubs roster is not excellent, and it’s not a significant improvement over the team that lost any sense of offense in September and made a quick exit of the playoffs yet again. Still, it’s progress towards the future, and this is likely a far more conservative estimate of how aggressive the team will be in terms of shaking up the roster. I’ve spent almost two full months thinking about this team since their Wild Card series loss and I still don’t know what I want the team to do or what my expectations are for 2021. Still, it bears repeating that no matter what we’re in one of the best eras of Cubs baseball ever, and yet again there’s a lot of potential on the roster to look forward to in 2021.

Ryan Ruhde

Cubs, Royals and general analysis writer. Emory University Psychology Major/Music Minor and Pre-Med, class of 2023. Find me on Twitter @ruhdolph

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