UPDATE: As the Chicago Cubs prepare for the winter meetings in Orlando, Florida, starting this week, they face crucial decisions that could shape their roster for the upcoming season. With just two signings—veteran reliever Phil Maton on a two-year deal and infielder Scott Kingery on a minor-league contract—the Cubs have significant gaps to fill, especially after falling just one win short of the National League Championship Series.
Amidst the urgency of the meetings, the Cubs have three pressing questions to address:
1. Will the Cubs Commit to Another Multiyear Reliever?
President of baseball operations Jed Hoyer has expressed a cautious approach to multiyear contracts for relievers, citing the volatility of bullpens. The Cubs’ bullpen showed promise in 2025 but remains a work in progress. With only Daniel Palencia returning as a high-leverage option, the question looms: will they add another proven arm on a multiyear deal? Hoyer noted, “It’s not my favorite thing to do… but I’ll never say never.”
2. How Will They Acquire a Top Starting Pitcher?
With Shota Imanaga accepting a $22.025 million qualifying offer, the Cubs’ rotation is set to look similar next season. However, improvements are necessary. The team must decide between pursuing free agents like left-hander Framber Valdez or right-hander Michael King, or making a trade for talents such as Joe Ryan from the Twins. The Cubs have the assets to make a significant trade, but will they act?
3. Are They Ready to Rely on Rookies as Tucker Explores Free Agency?
As star outfielder Kyle Tucker explores free agency, the Cubs may turn to rookies Moisés Ballesteros and Owen Caissie to fill the void. With Tucker’s future uncertain, the Cubs are contemplating a lineup shift, moving Seiya Suzuki back to right field and offering the designated hitter role to the young prospects. This strategy could be risky, but both rookies have shown promise, with Caissie dominating at Triple-A Iowa.
The Cubs’ leadership is weighing the options: invest in proven players like third baseman Alex Bregman or trust in their young talent. With the winter meetings fast approaching, every decision will impact the Cubs’ chances of success in the 2026 season.
This week promises to be pivotal for the Cubs as they navigate the complexities of roster construction. Fans and analysts alike will be watching closely to see how the team responds to these pressing challenges.
Stay tuned for live updates as the Cubs make their moves in Orlando.
