Chicago Cubs Face Critical Decisions Ahead of Winter Meetings

URGENT UPDATE: The Chicago Cubs are facing pivotal roster decisions as they head to the winter meetings this week in Orlando, Florida. Following only two offseason moves—signing veteran reliever Phil Maton to a two-year deal and infielder Scott Kingery to a minor-league contract—the Cubs have critical gaps to fill before the 2026 season.

The Cubs are in urgent need of multiple relievers and ideally another significant starting pitcher as they strategize on replacing star outfielder Kyle Tucker, who is exploring free agency. With their 2025 season ending just one win shy of the National League Championship Series, the stakes could not be higher.

As the meetings approach, the Cubs face three pressing questions:

1. Will the Cubs Commit to Another Multiyear Reliever?

President of baseball operations Jed Hoyer has been vocal about his preference for shorter commitments in the bullpen. While the Cubs managed to build a stronger bullpen in 2025 without long-term contracts, they now enter the offseason with only one reliable piece returning.

“It’s not my favorite thing to do. I prefer shorter commitments in the bullpen, but I’ll never say never,” Hoyer stated recently.

With Maton already signed, will the Cubs be willing to invest in another proven reliever? A decision to do so would signal a desire for stability in a bullpen that previously struggled.

2. How Will They Obtain a Top-of-the-Rotation Arm?

The Cubs’ rotation could look familiar next season with left-hander Shota Imanaga accepting a $22.025 million qualifying offer. However, the team needs to bolster its starting lineup, especially in terms of effectiveness and depth.

While the rotation currently includes Imanaga, Jameson Taillon, and Cade Horton, there are still avenues to acquire a top-tier pitcher. The Cubs must weigh the options of pursuing talent through free agency or trading.

Notable free-agent targets include left-handers Framber Valdez and Ranger Suárez. The Cubs also have the potential to trade for high-caliber players like Joe Ryan of the Twins or MacKenzie Gore of the Nationals, provided they can negotiate favorable terms.

3. Are the Cubs Ready to Rely on Rookies to Replace Tucker?

With Tucker’s future uncertain, the Cubs appear ready to hand significant at-bats to rookies Moisés Ballesteros and Owen Caissie. If Tucker departs, this decision could redefine the team’s offensive strategy, particularly with a shift of Seiya Suzuki back to right field to accommodate the young players.

While this approach may seem risky, Ballesteros has shown promise in limited play, and Caissie’s impressive performance in Triple-A has the organization optimistic. However, the Cubs could still pivot to a more experienced option, such as third baseman Alex Bregman, who was previously linked to the team.

As the Cubs continue their preparations for the winter meetings, all eyes will be on how they navigate these crucial decisions. The outcomes will significantly impact their chances for success in the upcoming season.

Stay tuned for further updates as the Cubs make critical moves in Orlando!