UPDATE: The Chicago Cubs are gearing up for the winter meetings this week in Orlando, Florida, facing critical roster decisions that could shape their 2026 season. 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 urgency to bolster their team is palpable.
As the Cubs prepare to navigate the free-agent and trade markets, they need to address multiple gaps, most notably in their bullpen and starting rotation, while also contemplating the potential loss of star outfielder Kyle Tucker to free agency.
1. Will the Cubs invest in another multiyear reliever?
President of baseball operations Jed Hoyer has previously expressed reluctance to hand out multiyear contracts to relievers, citing the volatility of bullpens. Despite the Cubs’ struggles last season, their bullpen emerged as a strength, built through shorter commitments. Hoyer stated, “It’s not my favorite thing to do…but I’ll never say never.” As the Cubs look to solidify their late-inning options, the question remains: will they extend another long-term deal after Maton’s signing?
2. How will they secure a top starting pitcher?
The Cubs’ rotation appears stable with returning arms like Shota Imanaga and Jameson Taillon, but they seek to enhance their starting options. The organization is weighing whether to pursue a proven ace through free agency or a trade. Recent reports suggest interest in Framber Valdez and Tatsuya Imai, a promising 27-year-old right-hander fresh off a standout season in Japan. Additionally, the Cubs could leverage their prospects to acquire talents like Joe Ryan from the Twins or MacKenzie Gore from the Nationals, depending on negotiations.
3. Are they ready to rely on rookies to fill Tucker’s shoes?
With Tucker exploring free agency, the Cubs seem poised to promote rookies Moisés Ballesteros and Owen Caissie to fill the void. This strategy may raise eyebrows, considering the potential risks of relying on unproven players. The Cubs are contemplating shifting Seiya Suzuki back to right field to accommodate at-bats for this young duo. While both players have shown promise, the Cubs may still explore options to bring in a more established player, with potential interest in third baseman Alex Bregman, who could enhance their lineup while providing flexibility in trades.
As the Cubs enter the winter meetings, all eyes are on how they will address these pivotal questions. The next few days will be critical as they aim to elevate a team that narrowly missed the National League Championship Series last season. Fans and analysts alike are eager to see how the Cubs will maneuver through this crucial offseason.
Stay tuned for the latest updates as the situation develops.
