Three questions facing the Chicago Cubs this offseason

As successful as the Chicago Cubs' season was, one cannot help but wonder "what if."

The Cubs won 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 in the NLDS after a bullpen game in Game 5, leaving the fanbase to wonder if a healthy rotation would have made a difference.

It is reasonable to expect the Cubs to be contenders again in 2026. The majority of their roster is already under contract next season. Despite that stability, the Cubs have several questions that need to be addressed in the offseason. 

Three questions facing the Chicago Cubs heading into the offseason

1. Can the Cubs retain outfielder Kyle Tucker?

The Cubs paid a significant price to acquire Tucker during the 2024-25 offseason, sending pitcher Hayden Wesneski, infielder Isaac Paredes and outfielder Cam Smith to Houston. He lived up to his billing in Chicago, posting a .266/.377/.464 batting line over 597 plate appearances, hitting 22 homers and 25 doubles. Although he has battled injuries over the past two seasons, Tucker is still regarded as the top free agent available this offseason.

The Cubs understand how coveted Tucker will be, with president of baseball operations Jed Hoyer saying that every team could use the soon-to-be free agent. Tucker said that playing for the Cubs was an honor, but that may not be enough to keep him in Chicago. Unless the Cubs are willing to spend a significant sum, he may end up as 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 homers and 37 doubles while stealing 35 bases. He saved five runs in center and was named a Gold Glove finalist as he dazzled with his range and impressive catches.

However, Crow-Armstrong's 2025 was a tale 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 homers and 21 doubles while stealing 27 bases as he appeared to be on the cusp of stardom. His production fell off in the second half as Crow-Armstrong slumped to a .216/.262/.372 batting line with six homers and 16 doubles while stealing eight bases. Crow-Armstrong is an impact player defensively, but for the Cubs to truly 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 as they missed starters Justin Steele and Cade Horton. While Horton should be ready for spring training and Steele should return in the first half of the 2026 season, there are questions in the rotation. Jameson Taillon was solid, but Shota Imanaga was not 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 such as Dylan Cease or Framber Valdez would go a long way toward fortifying a pitching staff that simply did not have enough in the postseason. The Cubs could also look to make another splash in the trade market should the Tigers make Tarik Skubal available.