Cubs’ pursuit of arms likely to continue at Winter Meetings

This story was excerpted from Jordan Bastian’s Cubs Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

CHICAGO -- The Cubs successfully constructed a playoff team last season, but the stated goal by president of baseball operations Jed Hoyer has been to create a group primed for a sustained period of October runs. That makes this an important winter for building on a roster that fell one win shy of reaching the National League Championship Series.

One of the reasons behind Chicago’s playoff exit was that the rotation had taken multiple hits by that stage, making depth in that area a must for this offseason’s to-do list. Chicago also needs to build up its bullpen corps and perhaps see if there could be an impact hitter out there to boost the lineup.

The arrival of the Winter Meetings in Orlando, Fla., will bring baseball executives, managers, agents and staff together under the same roof, helping momentum in both free agency and trade discussions. While the Cubs have made a few early moves and have been holding talks on multiple fronts, the Meetings have a way of spurring action.

Here is where things stand for the Cubs as the Meetings loom:

Club needs
The top priority for the Cubs heading into this offseason was to add to the front-end of the rotation and bring in multiple arms for the bullpen. Shota Imanaga’s decision to accept a one-year qualifying offer helped on the rotation front, as did Chicago’s signing of reliever Phil Maton (two years, $14.5 million), but there is still work to be done.

Adding one more bona fide starting pitcher (Ranger Suárez, Michael King, Tatsuya Imai and Zac Gallen have been linked to the Cubs) would really strengthen that group. And with nearly the entirety of the Cubs’ late-inning arms hitting free agency (notably: Brad Keller, Caleb Thielbar and Drew Pomeranz), the ballclub is going to target a variety of options via trade, free agency or other smaller transactions.

Potential trade candidates
If the Cubs were to try to pry a front-end starter away from another team via trade, the likely trade chips would be from Chicago’s farm system. Top 100 prospects like outfielder Owen Caissie (No. 47), catcher Moisés Ballesteros (No. 53) and righty Jaxon Wiggins (No. 67) would be high on the list for rival clubs. The chances of them being dealt away, however, seem low.

Caissie and Ballesteros are in position to impact the ‘26 Cubs, and the team’s pool of pitching prospects really thins out behind Wiggins. There’s a chance he makes his debut next season, too. Behind that trio, former Top 100 outfielder Kevin Alcántara could potentially be dangled in trades, given he is out of Minor League options and currently projects for a bench role on the Cubs roster.

Prospect to know
The Cubs selected the 24-year-old Wiggins with the No. 68 pick in the 2023 Draft as a compensatory pick for Willson Contreras exiting via free agency. Chicago took a chance on Wiggins after he had Tommy John surgery while at the University of Arkansas, believing in his athleticism and potential for a high-octane arsenal.

Wiggins impressed in ‘25, working his way through High-A South Bend, Double-A Knoxville and Triple-A Iowa and posting a 2.19 ERA in 19 outings (18 starts). In 78 innings, the righty used his upper-90s fastball, slider and changeup to rack up 97 strikeouts against 36 walks with only 44 hits allowed. Wiggins is in position to potentially reach Chicago in ‘26.

Rule 5 Draft
The Cubs have pick No. 25 in the upcoming Rule 5 Draft, which is scheduled for 1 p.m. CT on Wednesday on the final day of the Meetings. With a need for bullpen depth and bench reinforcements, it’s possible Chicago looks at the pool of available players and takes a flier on one for an extended look in the spring. That was what the Cubs did last year with the pick of Gage Workman, who earned an MLB role, but did not stick with the North Siders.

As a refresher, eligible players include those signed at age 18 or younger who were not added to a team’s 40-man roster within five seasons, or those 19 or older who were not added within four seasons. Teams pay a $100,000 fee to pick a player in the MLB phase, and he is required to stay on the 26-man roster for the full season (or be offered back to former team for $50,000).

Burning question
Will the Cubs target an impact bat like free agent Alex Bregman?

The Cubs knew that trading for star outfielder Kyle Tucker last offseason might very well lead to a one-year partnership between the team and player. With Tucker on the free-agent market, Chicago is tasked with either trying to keep him in the fold or looking for other ways to upgrade the offense. Now, the Cubs have Seiya Suzuki for right field, plus Caissie and Ballesteros ready to help the lineup. It’s possible the team goes with the pieces already in place, especially with pitching being the biggest need. That said, the Cubs’ front office has surprised before, and it was just last spring that they stayed in on Bregman until the very end. And Chicago has, unsurprisingly, been linked to the third baseman again in recent reports.