UPDATE: The Chicago Cubs are facing critical roster decisions just days before the winter meetings in Orlando, FL, set to begin on December 4, 2025. After minimal activity this offseason, including signing veteran reliever Phil Maton to a two-year deal and infielder Scott Kingery to a minor-league contract, the team is under pressure to strengthen its lineup.
With the Cubs falling just one win short of the National League Championship Series last season, the urgency to enhance their roster has never been greater. Key questions loom over the team’s strategy as they aim to fill gaps left by Kyle Tucker, who is exploring free agency.
1. Will the Cubs commit to another multiyear reliever?
Cubs President of Baseball Operations Jed Hoyer has expressed reluctance in offering multiyear contracts to relievers due to the unpredictable nature of bullpens. However, with only Daniel Palencia returning among key bullpen pieces, the Cubs may need to reconsider their strategy. Hoyer noted, “It’s not my favorite thing to do… but I’ll never say never.” The decision to sign Maton indicates a potential shift in their approach.
2. How will they acquire an effective starting pitcher?
Despite Shota Imanaga accepting a qualifying offer, the Cubs still seek to enhance their starting rotation. They have several options, including potential trades for Joe Ryan from the Minnesota Twins or MacKenzie Gore from the Washington Nationals. Free agent targets include left-handers Framber Valdez and Ranger Suárez. The Cubs must weigh the benefits of trading valuable prospects against financial commitments to free agents.
3. Are they ready to rely on rookies to replace Tucker?
As Tucker considers his free agency options, the Cubs are looking at rookies Moisés Ballesteros and Owen Caissie to fill his shoes. This bold strategy may risk the team’s competitiveness, especially if the rookies struggle. Hoyer’s focus on internal talent could change if they pursue experienced players like Alex Bregman, who previously showed interest in joining the Cubs.
As the winter meetings approach, the Cubs’ decisions will significantly shape their 2026 season. The clock is ticking, and fans are eager to see how the front office responds to these pressing challenges. Stay tuned for live updates from the winter meetings as the Cubs aim to bolster their roster and make a strong push for the upcoming season.
