UPDATE: The Chicago Cubs are at a critical juncture as they prepare for the winter meetings in Orlando, FL, this week. With only two signings—veteran reliever Phil Maton on a two-year deal and infielder Scott Kingery on a minor-league contract—the Cubs are racing against time to reshape their roster following a season that left them just one win shy of the National League Championship Series.
As the meetings approach, three pressing questions loom over the Cubs’ strategy.
1. Will the Cubs commit to another multiyear reliever deal?
President of baseball operations Jed Hoyer has historically shied away from long-term commitments for relief pitchers, given the unpredictable nature of bullpens. Despite the Cubs’ bullpen struggles last season, they found success with a flexible approach. Hoyer stated, “It’s not my favorite thing to do. I prefer shorter commitments in the bullpen, but I’ll never say never.” With only one reliable arm returning, the urgency to solidify the bullpen is clear.
2. How will the Cubs secure an effective starting pitcher?
The Cubs’ rotation appears stable on paper with returning arms like Jameson Taillon and Justin Steele, who is recovering from elbow surgery. However, an increase in performance is needed. The organization faces a pivotal decision: pursue a top-of-the-rotation starter via free agency or trade. With Dylan Cease‘s hefty contract serving as a cautionary tale, the Cubs are exploring other options, including Tatsuya Imai, a promising right-hander from Japan, and potential trades for Joe Ryan or MacKenzie Gore.
3. Are they ready to rely on rookies to replace Kyle Tucker?
With Kyle Tucker exploring free agency and potentially leaving the Cubs, the team may turn to rookies Moisés Ballesteros and Owen Caissie to fill the void. This risky strategy could pay off, as both players have shown promise in previous seasons. Hoyer’s comment on internal options suggests a shift in approach, but the Cubs still have the flexibility to pursue established players like Alex Bregman if necessary.
The Cubs’ decisions in the coming days will not only shape their roster but could determine their competitiveness in the 2026 season. As the clock ticks towards the winter meetings, fans and analysts alike are eagerly anticipating the moves that could define the Cubs’ future.
Stay tuned for further updates as the Chicago Cubs navigate these critical decisions and strive to enhance their roster for the upcoming season.
