UPDATE: The Chicago Cubs are at a pivotal moment as they prepare for the winter meetings in Orlando, Florida this week. With only two moves made so far—signing veteran reliever Phil Maton to a two-year deal and infielder Scott Kingery to a minor-league contract—the team is under pressure to strengthen their roster significantly.
As the Cubs aim to bounce back from a season that left them just one win shy of the National League Championship Series, they face three urgent questions that could define their strategy moving forward.
1. Will the Cubs invest in another multiyear reliever? Cubs President of Baseball Operations Jed Hoyer has previously expressed reluctance to commit to long-term deals for relievers, citing the bullpen’s volatility. Last week, they signed Maton, but with only Daniel Palencia returning to the bullpen, the Cubs must consider whether to take a chance on another high-leverage arm. “It’s not my favorite thing to do. I prefer shorter commitments in the bullpen,” Hoyer stated, emphasizing the need for flexibility in constructing the team.
2. How will they secure an effective starting pitcher? With left-hander Shota Imanaga accepting a $22.025 million qualifying offer, the Cubs’ rotation appears stable on paper. However, they are exploring options for a top-of-the-rotation arm to elevate their pitching staff. Potential targets include left-handed starters Framber Valdez and Ranger Suárez, as well as right-hander Michael King. In trade discussions, the Cubs may pursue Joe Ryan from the Minnesota Twins or MacKenzie Gore from the Washington Nationals, utilizing their prospect capital to enhance their roster.
3. Are they prepared to rely on rookies to replace Kyle Tucker? With Kyle Tucker exploring free agency and not likely to return, the Cubs are considering giving significant at-bats to rookies Moisés Ballesteros and Owen Caissie. This decision could reshape the team’s lineup, especially if Seiya Suzuki shifts back to right field to accommodate the young players at designated hitter. While this strategy presents risks, it also reflects the Cubs’ commitment to nurturing their prospects.
As the clock ticks down to the winter meetings, the Cubs’ decisions will have immediate implications for their 2026 season. The team has the flexibility to pivot if necessary, potentially exploring external options like third baseman Alex Bregman, who could fill the void left by Tucker.
Expect the Cubs to make decisive moves in the coming days as they aim to bolster their roster and compete for a championship. Stay tuned for updates as developments unfold in Orlando.
