3 questions facing the Chicago Cubs this offseason

The Chicago Cubs entered the 2026 season as a favorite to reach the postseason.

They lived up to those expectations, finishing 89-73. However, the San Diego Padres swept the Cubs in the wild-card round as they couldn't overcome several pitching injuries and a sudden lack of offense.

The Cubs face what could be a brutal offseason. Key players such as outfielders Ian Happ and Seiya Suzuki, pitchers Shota Imanaga, Kevin Gausman, Clay Holmes and Matthew Boyd and catcher Carson Kelly are free agents. The Cubs have a lot of work to do in order to remain in the playoff hunt in 2027.

Three questions facing the Chicago Cubs

1. Can the Cubs rebuild their rotation?

The Cubs rotation may look a lot different in 2027. Imanaga, Gausman, Holmes, Boyd, Colin Rea and David Peterson are free agents. While Edward Cabrera will return, he battled injuries and ineffectiveness in his first season in Chicago. Pitchers Ben Brown and Justin Steele will be looking to return from injuries of their own.

The Cubs have internal options to help fortify the rotation. Although they declined Javier Assad's option for 2027, he is under team control through arbitration and pitched reasonably well in 2026. However, if the Cubs are going to contend for a playoff berth, they will need to find at least one more top-of-the-rotation starter.

2. How do the Cubs fill their outfield vacancies?

The pitching staff is not the only area of concern. Happ and Suzuki are free agents and may return to the Cubs, though a short-term deal for Happ could be possible. Having probable NL MVP Pete Crow-Armstrong in center helps, but the Cubs other candidates are either better fits as a utility option or in a backup role. Prospect James Triantos had some outfield experience in the minors, as does utility man Matt Shaw, if the Cubs want to look at potential internal options.

The Cubs could find help in free agency. Ryan Divish of the Seattle Times listed the Cubs as a possible landing spot for left fielder Randy Arozarena. He would give the Cubs another dynamic offensive threat in the lineup, and although he is not on Happ's level defensively, Arozarena is a solid defensive outfielder. 

3. What do the Cubs do behind the plate?

Although Carson Kelly was unable to replicate his stellar 2025 performance, he was a solid bat in the Cubs lineup. He posted a .258/.336/.376 batting line in his 425 plate appearances, hitting 10 homers and 15 doubles. Kelly has been valuable defensively as well, helping to shut down the running game.

The Cubs do not have a proven option waiting in the wings. Miguel Amaya is a former top prospect and has done reasonably well when he has been healthy. Owen Ayers has gone from a 19th-round selection in the 2024 MLB Draft to the Cubs' second-best prospect, per MLB.com, and could be the future at the position. However, adding a veteran backstop as an insurance option would make sense if Kelly signs elsewhere.