Chicago Cubs Face Urgent Roster Decisions Ahead of Winter Meetings

UPDATE: The Chicago Cubs are gearing up for critical roster decisions as they head into the winter meetings this week in Orlando, Florida. With only two offseason moves made—signing veteran reliever Phil Maton to a two-year deal and adding infielder Scott Kingery on a minor-league contract—the Cubs are under pressure to address key gaps before the season starts.

As they prepare for the meetings, the Cubs are facing three urgent questions that could shape their 2026 season. First, will they commit to another multiyear contract for a reliever? President of baseball operations Jed Hoyer has hinted at a preference for shorter contracts, citing the volatility of bullpens. However, with only one established back-end arm returning, the team’s future hinge on whether Hoyer will change his strategy.

“It’s not my favorite thing to do. I prefer shorter commitments in the bullpen, but I’ll never say never,” Hoyer stated last month regarding multiyear contracts for relievers. As the offseason progresses, the Cubs must decide if they’ll gamble on another long-term deal to solidify their bullpen.

Secondly, how will the Cubs acquire an effective starting pitcher? The return of left-hander Shota Imanaga after accepting a $22.025 million qualifying offer means the rotation will closely mirror last season’s. However, the Cubs still need to boost their pitching capabilities. They are weighing the options between free agency and trades, especially after Dylan Cease’s hefty contract with the Toronto Blue Jays indicated a financial threshold the Cubs might not want to breach.

Potential targets include Japanese right-hander Tatsuya Imai and established MLB pitchers like left-handers Framber Valdez and Ranger Suárez. In trades, pitchers like Joe Ryan from the Twins and MacKenzie Gore from the Nationals could be on the table, depending on negotiations.

Lastly, are the Cubs truly ready to rely on rookies to fill the void left by Kyle Tucker? With Tucker exploring free agency and the Cubs not being frontrunners to sign him, the team is looking at Moisés Ballesteros and Owen Caissie to step into significant roles. This decision could prove risky as both players lack extensive major-league experience.

The Cubs have the flexibility to pivot if necessary. Notably, third baseman Alex Bregman could be a viable option, given previous interest during last year’s free agency. Signing Bregman might allow the Cubs to utilize Matt Shaw in various roles or trade him to enhance their pitching staff.

As the Cubs enter the winter meetings, all eyes will be on how they navigate these pivotal roster challenges. Fans and analysts alike are eager to see if the team can turn its recent near-success into tangible improvements before the 2026 season kicks off. Stay tuned for live updates as the situation develops!