UPDATE: The Chicago Cubs are gearing up for urgent roster decisions as they head into the winter meetings this week in Orlando, Florida. With only two offseason moves made—signing veteran reliever Phil Maton to a two-year deal and infielder Scott Kingery to a minor-league contract—the team faces critical questions that could shape their 2026 season.
As the Cubs prepare to enhance a roster that narrowly missed the National League Championship Series, they must determine how to fill key gaps, particularly in their bullpen and starting rotation. Jed Hoyer, President of Baseball Operations, is under pressure to make impactful decisions that resonate with fans and stakeholders alike.
1. Will the Cubs invest in another reliever?
Hoyer has historically preferred shorter commitments for relievers, citing the volatility of bullpens. Yet, with only Daniel Palencia returning, the Cubs may reconsider their strategy. “It’s not my favorite thing to do,” Hoyer acknowledged regarding multiyear contracts for relievers, “but I’ll never say never.” With the offseason in full swing, fans are eager to see if the Cubs will opt for another long-term deal to stabilize their bullpen.
2. How will they secure an effective starting pitcher?
The Cubs’ starting rotation currently includes Shota Imanaga, who accepted a $22.025 million qualifying offer. However, the team seeks a top-of-the-rotation arm to bolster their pitching depth. Potential targets include free agents like Framber Valdez and Tatsuya Imai, who recently made waves in Nippon Professional Baseball. The Cubs also have attractive trade options, including Joe Ryan from the Twins and MacKenzie Gore from the Nationals. The decision between pursuing free agency or trade could determine the Cubs’ competitive edge in the upcoming season.
3. Are they willing to trust rookies to replace Kyle Tucker?
With Kyle Tucker exploring free agency, the Cubs are contemplating a bold move by giving significant playing time to rookies Moisés Ballesteros and Owen Caissie. While this strategy could pay off, it poses a substantial risk for a franchise aiming for postseason success. “We believe these young players are ready for the challenge,” a source within the organization stated. If the Cubs decide against relying solely on their prospects, they may pursue established players like Alex Bregman to fill the gap left by Tucker.
As the winter meetings approach, all eyes will be on the Cubs to see how they navigate these pivotal decisions. The outcome could significantly influence the trajectory of the franchise for the coming season, making it a crucial moment for team management and fans alike.
Stay tuned for updates as this story develops. The Cubs have the flexibility to pivot and improve their lineup, and fans are eager for results that reflect the team’s ambition to contend for the title.