The Chicago Cubs still have a lot of work to do on their roster.
As the Cubs head to the winter meetings this week in Orlando, Fla., they have made only two moves: signing veteran reliever Phil Maton to a two-year deal and signing infielder Scott Kingery to a minor-league deal with an invitation to big-league spring training. The Cubs still need multiple relievers and ideally another significant starting pitcher while figuring out how they might replace Kyle Tucker.
There are multiple avenues the Cubs can take to improving a roster that fell one win shy of the National League Championship Series. They face three questions with the winter meetings approaching.
1. Will the Cubs give another reliever a multiyear contract?
President of baseball operations Jed Hoyer has been on the record about preferring to avoid giving relievers multiyear contracts.
Bullpens are notoriously volatile, and while the Cubs struggled to put together a reliable group, especially their back-end arms, year to year, their 2025 pen became a strength. The Cubs built the group without committing multiple years to their high-leverage arms. That gives them flexibility for how they want to construct the 2026 version but also means they came into the offseason having only one or two puzzle pieces in place to envision what the bullpen could look like for manager Craig Counsell.
The Cubs gave Maton a two-year contract for the team’s first move of the offseason during the last week of November. Will Hoyer and the front office be willing to give out another multiyear deal for a proven reliever? A willingness to do so would indicate the Cubs want fewer question marks in a bullpen that essentially returns only Daniel Palencia.
“It’s not my favorite thing to do. I prefer shorter commitments in the bullpen, but I’ll never say never,” Hoyer said of multiyear contracts for relievers at the general manager meetings last month. “We offered some last year (and) we didn’t win the bidding. So it’s not a hard and fast rule, but you can guess that we’re probably going to be more focused on shorter commitments.”
2. How will they acquire an effective starting pitcher?
Shota Imanaga’s decision to accept the Cubs’ $22.025 million qualifying offer sets up the 2026 rotation to look very similar to last season.
With Imanaga, Jameson Taillon, Cade Horton, Matthew Boyd and Colin Rea back plus Justin Steele on track to be ready early in the season following left-elbow surgery, the rotation on paper doesn’t appear to be a need. The Cubs, however, could use an uptick in stuff from their starters. While they also will be looking to address pitching depth, there are paths the Cubs can take to acquire a top-of-the-rotation arm.
Ultimately, the Cubs must decide whether to pursue that in free agency or through a trade. Dylan Cease’s seven-year, $210 million contract with the Toronto Blue Jays proved to be a level the Cubs didn’t want to go to, though deferrals in the deal reduce the value of Cease’s contract to $184.6 million.
They still have intriguing options. Japanese right-hander Tatsuya Imai, 27, was posted on Nov. 18 following a dominant run in Nippon Professional Baseball with the Saitama Seibu Lions. Among free-agent starters, left-handers Framber Valdez and Ranger Suárez and right-hander Michael King could fit what the Cubs need. In a trade, the Cubs have the pieces to make a potential move for Twins right-hander Joe Ryan and Nationals left-hander MacKenzie Gore happen — if those teams are willing to find more common ground than the high demands at the trade deadline.
A trade might make more sense for the Cubs to allow them to use their prospect capital and allocate their financial resources elsewhere on the roster.
3. Are they truly willing to roll with two rookies to replace Tucker?
As Tucker explores his options in free agency and the Cubs not considered among the front-runners for him to return to Chicago, the organization sounds willing to give the star’s at-bats to a pair of rookies.
Moisés Ballesteros and Owen Caissie are in line to get big-league at-bats should Tucker sign elsewhere. By shifting Seiya Suzuki back to right field, it would open at-bats for the young duo at designated hitter. It certainly would be a gamble for the Cubs to go with less proven options rather than acquire someone with a better major-league track record. Ballesteros impressed the Cubs by his approach in his limited action, while Caissie’s dominance for two consecutive seasons with Triple-A Iowa has the team believing he is ready for the challenge.
As the Cubs continue to evaluate the free-agency and trade markets, they could instead look to find a way to better close the gap between Tucker and whomever they give his at-bats to. If the Cubs don’t want to rely solely on prospects, third baseman Alex Bregman makes a lot of sense. Both sides were interested in each other during his free agency last offseason that landed him in Boston on a multiyear deal that had an opt-out he took after the season. Signing Bregman, 31, would allow the Cubs to move Matt Shaw around the field or make him a key piece of a trade to land a top starting pitcher.
Despite initially sounding inclined to look internally to replace Tucker, the Cubs have the flexibility to pivot and find a way to improve a lineup that was at its best when their star hitter was healthy and locked in.