As successful as the Chicago Cubs’ season was, it makes you wonder “what if.”
The Cubs won more than 90 games for the first time since 2018 and reached the postseason for the first time since 2020. The Cubs even advanced beyond the wild card round for the first time since 2017. However, the Cubs were eliminated from the NLDS after a bullpen contest in Game 5, leaving the fanbase to wonder if a healthy rotation would have made a difference.
It’s reasonable to expect the Cubs to be contenders again in 2026. Most of their selection is already under contract next season. Despite that stability, the Cubs have several questions that need to be answered this offseason.
Three questions facing the Chicago Cubs heading into the offseason
1. Can the Cubs keep outfielder Kyle Tucker?
The Cubs paid a significant price to acquire Tucker during the 2024-2025 offseason, sending pitcher Hayden Wesneski, infielder Isaac Paredes and outfielder Cam Smith to Houston. He lived up to his expectations in Chicago, posting a .266/.377/.464 batting line over 597 plate appearances, hitting 22 home runs and 25 doubles. Although he has struggled with injuries over the past two seasons, Tucker is still considered a player the best free agent available this low season.
The Cubs understand how coveted Tucker will be president of baseball operations Jed Hoyer says that any team could use the soon-to-be free agent. Tucker said playing for the Cubs was an honor, but that might not be enough to keep him in Chicago. Unless the Cubs are willing to spend a significant amount of money, he could be a one-year rental.
2. Which player is outfielder Pete Crow-Armstrong?
On the surface, Crow-Armstrong had an excellent year with the Cubs. He posted a solid .247/.287/.481 batting line in 647 plate appearances, hitting 31 home runs and 37 doubles while stealing 35 bases. He saved five points in the center and was named a Golden Glove Finalist as he dazzled with his range and impressive catches.
Crow-Armstrong’s 2025, however, was a story of two halves. He was excellent in the first half of the season, posting a .265/.302/544 batting line over 401 plate appearances, hitting 25 home runs and 21 doubles while stealing 27 bases, as he seemed to be on the brink of stardom. His production dipped in the second half as Crow-Armstrong dropped to a .216/.262/.372 batting line with six home runs and 16 doubles while stealing eight bases. Crow-Armstrong is an impact player defensively, but if the Cubs really want to take the next step, they need him to be the offensive dynamo he was in the first half of 2025.
3. Do the Cubs have enough in the rotation?
The holes in the Cubs’ rotation were evident in October when they were missing starters Justin Steele and Cade Horton. While Horton should be ready for spring training and Steele should return for the first half of the 2026 season, questions arise around the rotation. Jameson Taillon was solid, but Shota Imanaga wasn’t the same pitcher after missing just over a month with a strained left hamstring. Matthew Boyd made more than 15 starts for the first time since 2019 and his 179.2 innings were more than he threw in the previous three years combined (124).
In addition to those question marks, the rotation lacks an impact arm. Adding a top-of-the-rotation arm like Dylan Cease or Framber Valdez would go a long way to bolstering a pitching staff that simply didn’t have enough in the postseason. The Cubs could also look to make another splash on the trade market if the Tigers make Tarik Skubal available.
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