Chicago Cubs Face Crucial Decisions Ahead of Winter Meetings

UPDATE: The Chicago Cubs are gearing up for critical roster decisions as the winter meetings kick off this week in Orlando, Florida. With only two offseason moves—signing reliever Phil Maton to a two-year deal and infielder Scott Kingery to a minor-league contract—the Cubs are under pressure to enhance their lineup.

As they prepare for the meetings, the Cubs face three urgent questions that will shape their immediate future.

1. Will the Cubs commit to another multiyear deal for a reliever? Cubs President of Baseball Operations Jed Hoyer has expressed reluctance to hand out long-term contracts to relievers, citing the volatility of bullpens. However, after a season that left them just one win shy of the National League Championship Series, the Cubs must consider if a proven arm can stabilize their late-game situations. With only Daniel Palencia returning from a shaky bullpen, the pressure is on. Hoyer previously stated, “It’s not my favorite thing to do. I prefer shorter commitments in the bullpen, but I’ll never say never.”

2. How will they secure a top starting pitcher? The Cubs’ starting rotation looks stable with returning faces like Shota Imanaga, Jameson Taillon, and Justin Steele, but they need to bolster their starting depth. The team is weighing options, including potential trades for high-impact pitchers like Joe Ryan of the Twins or MacKenzie Gore of the Nationals. They have also shown interest in free agents like Framber Valdez and Tatsuya Imai, who was recently posted from Japan. With the market evolving, the Cubs must decide between a trade or free agency to enhance their rotation.

3. Are they ready to rely on rookies to replace Kyle Tucker? As Kyle Tucker explores free agency, the Cubs are considering giving his at-bats to rookies Moisés Ballesteros and Owen Caissie. This risky strategy could pay off, as both young players have shown promise, but it also raises concerns about experience in the lineup. By shifting Seiya Suzuki to right field, the Cubs would create opportunities for the rookies. However, pursuing established players like Alex Bregman could mitigate the risk of relying solely on untested talent.

As the winter meetings unfold, the Chicago Cubs must act decisively to address these pressing questions. With the deadline drawing near, their choices will have immediate implications for their competitiveness in the upcoming season. Fans and analysts alike will be watching closely as the Cubs navigate this pivotal moment in their franchise history.

Stay tuned for live updates as developments unfold from Orlando. The Cubs’ strategy could reshape their roster and impact their pursuit of a championship.