Chicago Cubs 2025 Offseason Outlook

The Chicago Cubs made the postseason this year for the first time since 2020. They finished 92-70 and finished 2nd in the NL Central. The season was a step in the right direction for a franchise that came into this year with a lot of uncertainty. Now with many important decisions to make, this offseason could determine if 2025 was a stepping stone or a blip on the radar. With Kyle Tucker’s impending free agency, uncertainty in the bullpen, and a looming work stoppage, it is going to be an interesting winter for the Chicago Cubs front office.

After a rampant offseason last winter that saw the Chicago Cubs jump from a team hovering around .500 to a contender in October, this offseason is going to have a different feel. The top question centers around player retention, namely Kyle Tucker, but also Brad Keller, who ended up filling in as Chicago’s closer by the end of the season.

Any player acquisition would come at a cost of prospect capital, and seeing how the Chicago Cubs value their burgeoning young players will determine how aggressive they are in improving the major league roster this winter.

Chicago Cubs Enter 2025 Offseason

The Chicago Cubs had their best season in recent memory in 2025. They made the playoffs for the first time in five years and won a playoff game for the first time in eight. After making plenty of moves to make this season happen last offseason, Chicago faces similar challenges in improving their team this winter. They have major issues coming up with player retention, farm system management, and payroll spending.

The headline and primary concern for the Chicago Cubs is going to be Tucker. As the season has gone on and reports around Tucker’s contract situation have come out, it’s looking less and less like the 28-year-old right fielder will be back at Wrigley Field in 2026.

Another key contributor from 2025 could be on the way out if the Chicago Cubs aren’t ready to pay market price for his services. Brad Keller was brought in during spring training on a minor league deal. By the end of the postseason, Keller was the team’s closer. With a team bereft of proven relievers, retaining Keller could be as crucial as bringing Tucker back.

Vision Of the Future

One of the reasons that retaining Keller could be more crucial to the Chicago Cubs’ success in 2026 is that if the team loses Kyle Tucker, they have Owen Caissie waiting in the wings to take his place in the lineup. Caissie is one of many prospects who are ready to make an impact at the major league level, but have veterans above them in the organization.

In addition to Caissie, the Chicago Cubs have Kevin Alcantara, Moises Ballesteros, Matt Shaw, Cade Horton, and Jaxon Wiggins as part of a crop of top prospects who could help propel the team to a perennial contender in the National League for years to come.

Horton and Shaw have established roles on the major league team already. Caissie, Ballesteros, and Alcantara have all seen some playing time with the Cubs, and Wiggins is anticipated to make his debut in 2026. One thing that the Chicago Cubs have to consider when making moves this winter is what role they have in mind for this group of young players who are undoubtedly ready to contribute at a higher level with the major league team.

Payroll Concerns

Unfortunately for the Chicago Cubs and their fans, the decisions the front office makes this offseason could be a factor of cost rather than effectiveness. If Caissie replaces Tucker on the Chicago Cubs roster, it could be a matter of financial rigidity on the part of ownership.

The Ricketts family has done a great job since taking over almost 16 years ago. One thing that could be improved on their end is a willingness to spend towards the top of the market, where they ought to be based on the revenue they generate.

The Chicago Cubs rank 26th in all of baseball in terms of percentage of revenue devoted to payroll. In 2024, they generated $584 million in revenue, with $213 million going to payroll. If the Chicago Cubs want to make a dramatic shift in how they operate, this is an obvious place to start. It could have drastic consequences for the 2025 offseason and beyond.