This story was excerpted from Jordan Bastian’s Cubs Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.
CHICAGO -- The small-sample nature of the National League Wild Card Series contributed to the end result for the Cubs: the bats went cold and the season came crashing to a close. The reality, however, was that issues in the preceding weeks and months led to a slide in the standings, the loss of home-field advantage and that harsh, disappointing ending.
The Cubs are now left to evaluate where things went wrong and how to best correct things for 2027 and beyond, starting with this offseason.
“We have a really good core position-player wise,” Cubs president of baseball operations Jed Hoyer said. “We have really good prospects [who are] kind of close to ready. I think we’re in a good, remarkably healthy position on the position-player side. I think we have to focus our resources and energy on the pitching side, predominantly.”
Here are five questions facing the Cubs this offseason:
1. How will the Cubs rebuild the rotation?
The North Siders risk losing the entire group that finished this season in the five-man rotation via free agency this offseason. Matthew Boyd (mutual option) and Clay Holmes (player option) have decisions looming, while Shota Imanaga, Kevin Gausman and David Peterson will simply hit the open market. Another depth arm, Colin Rea, has a team option for next season as well.
In his end-of-season media session, Hoyer said the team needs to do a deep dive into everything that went wrong on the pitching front. Part of that will include examining which arms best fit Chicago’s defense-heavy model. That, in turn, will naturally lead to prioritizing which free-agent arms to try to retain. Boyd, Holmes and Peterson did a solid to above-average job at keeping the baseball in the yard on a team that led the National League in homers allowed (231).
The Cubs also need to factor in the unknowns surrounding the respective injury comebacks from Ben Brown, Cade Horton and Justin Steele. It is just not clear how many collective innings that group can be counted on for ’27. Chicago also needs to get more out of Edward Cabrera, who fell well short of expectations due to a combination of poor performance and injury woes.
2. Will the Cubs re-sign Ian Happ and/or Seiya Suzuki?
It is one thing to lose one corner outfielder, but the Cubs might lose their four-time Gold Glove Award winner in left (Happ) and arguably their best right-handed power threat in right (Suzuki). Hoyer gave the reality of the situation in his recent press conference when he said: “We can’t retain everyone.”
The free-agent class on the hitting front this offseason is relatively weak, compared to recent winters. As a result, Suzuki is expected to be one of the best bats available. For a Cubs front office that tends to hold the line on its value-based contract offers, that makes re-signing Suzuki seem less likely at the moment.
As for Happ, he has spent the past 10 years with the Cubs and has developed into a clubhouse leader and revered teammate. While he moved more into a platoon-type role down the stretch, given his struggles against lefty pitching, Happ still offered plus production (+6 Fielding Run Value and 107 wRC+). Maybe there is a path to a short-team deal to avoid having two holes in the outfield.
3. How will the Cubs fix the bullpen?
Hoyer showed a willingness to veer outside his usual approach to bullpen building last offseason with a series of free-agent signings, but the results fell short during the season. Injuries riddled the staff throughout the year and there was a constant churn of pitchers. The Cubs set a single-season club record with 14 players notching at least one save.
“I did a poor job on the bullpen this year -- full stop,” Hoyer said. “We didn’t get right. That’s something we’ve spent a lot of time talking about already, and we’ll continue to talk about it. I take responsibility for that, and it’s something we’ll look to improve on this offseason, because it didn’t work out as it did in 2025 as it did this year.”
4. How do Matt Shaw and Pedro Ramírez fit?
Given the locked-in nature of the Cubs’ position-player group, Shaw and Ramírez found themselves in versatile utility roles in ’26. Shaw helped out in the outfield and filled in, as needed, in the infield. Ramírez was a bench player, but he got runway as a regular when shortstop Dansby Swanson was sidelined in the second half. One (or both) could get a chance as a new corner outfielder, if Happ and/or Suzuki do not return.
“I think we’ll lean on both those guys more heavily going forward,” Hoyer said.
5. How will the catching tandem look in ’27?
Carson Kelly has a mutual option for ’27, so there is a strong chance the veteran catcher enters free agency. Behind him, the Cubs have Miguel Amaya, who played 83 games this past season and is capable of being a No. 1 catcher. The bigger question is will the Cubs look at this as a chance to bring prospect Owen Ayers (MLB Pipeline’s No. 2 Cubs prospect and No. 88 on the Top 100 list) into the fold right away. Ayers spent the past couple weeks of the season around Chicago’s big league team to begin gaining familiarity with the MLB staff.