UPDATE: The Chicago Cubs are gearing up for critical roster decisions as they head to the winter meetings in Orlando, Florida, this week. With only two offseason moves made, including signing veteran reliever Phil Maton to a two-year deal and infielder Scott Kingery to a minor-league contract, the team faces significant questions that could shape their 2026 season.
The Cubs are looking to bolster their bullpen and starting rotation while navigating the potential loss of outfielder Kyle Tucker, who is exploring free agency. As the meetings approach, three pivotal questions stand out:
1. Will the Cubs Sign Another Proven Reliever?
President of baseball operations Jed Hoyer has expressed hesitance in committing to multiyear contracts for relievers, citing the volatility of bullpens. However, with only Daniel Palencia returning from last season’s group, the Cubs must decide whether to secure another reliable arm or continue building flexibility. Hoyer noted, “I prefer shorter commitments in the bullpen, but I’ll never say never,” indicating possible openness to a change.
2. How Will They Acquire a Top Starting Pitcher?
With left-hander Shota Imanaga accepting a $22.025 million qualifying offer, the rotation seems stable on paper. However, the Cubs need to enhance their pitching depth. They face a critical decision on whether to pursue free agency or trades to secure a top-of-the-rotation arm. Notably, options like Framber Valdez and Tatsuya Imai could be on their radar, while trade possibilities exist with teams like the Minnesota Twins for Joe Ryan.
3. Are They Prepared to Rely on Rookies to Replace Tucker?
As Tucker weighs his options, the Cubs are considering handing significant playing time to rookies Moisés Ballesteros and Owen Caissie. This move could be a gamble, given the players’ lack of MLB experience. While the Cubs may look internally for solutions, they could also pursue established players like Alex Bregman to better bridge the gap left by Tucker.
The Cubs’ impending decisions at the winter meetings could drastically reshape their roster and impact their chances for the upcoming season. Fans and analysts alike are eager to see how the team navigates these pivotal moments. With their postseason aspirations on the line, the urgency for strategic moves is palpable.
Stay tuned for updates as the Cubs address these crucial questions during the winter meetings.
