The Chicago Cubs are heading into a winter where the margins matter as much as the marquee names. After watching a division rival claim the World Series crown, the pressure to claw back to the top of the NL Central is only growing, and the work ahead looks substantial.
Pitching is the center of the conversation, and that starts with a rotation and bullpen that both need real reshaping. Several Cubs players have already declined their player options, including Matthew Boyd and Clay Holmes, which only adds to the list of decisions Jed Hoyer has to sort through. The farm system needs a boost, the pitching infrastructure needs an overhaul, and if the Cubs are going to keep pace with Milwaukee and the rest of the league’s heavyweights, they’ll need more than splashy headlines.
That’s why the underrated names on the market might matter just as much as the stars. There are holes to fill beyond the mound, too, and catcher is one of them.
Carson Kelly is set to become a free agent, Miguel Amaya is there, and Owen Ayers could get a call-up. Even so, adding a proven veteran would make sense, and Tyler Stephenson fits that description.
The former Reds catcher would step right in as the Cubs’ starting catcher and help address one of the offseason’s biggest questions. A tandem of Stephenson and Amaya could be an upgrade behind the plate, and the price tag looks manageable. Jim Bowden of The Athletic listed the Cubs among Stephenson’s best fits, projecting him at two years and $16 million.
There’s plenty to like beyond the role he’d fill. Stephenson is one of the better defensive catchers in the sport, ranking third in the league in pitch blocking and posting a 78.0 percent success rate with ABS challenges. He also brings real offense, carrying a .757 OPS for his career and hitting 13 or more homers in four straight seasons.
The bullpen is another area where depth could pay off quickly. The Cubs need late-inning arms they can trust, especially setup help that can handle high-leverage spots with consistency. Bryan Abreu checks a lot of those boxes, and he’d give the Cubs a serious boost right away.
If Chicago landed Abreu, he might be the best arm in the bullpen on day one. He could pair with Ryan Zeferjahn to give the Cubs two high-velocity setup options, and he’d bring playoff experience along with championship polish.
Abreu started slowly, then finished 6-4 with a 3.73 ERA and 80 strikeouts. He also posted a nearly 30.0 percent K rate, and his whiff rate was in the 97th percentile, per Baseball Savant.
Abreu wouldn’t come cheap, but that’s part of the appeal. The Cubs need proven relief help, and he fits the bill.
The rotation picture is less certain, especially if the Cubs decide to look outside the organization for a bigger swing. Tarik Skubal, Michael King, Freddy Peralta and Reid Detmers are the kinds of names that would change the conversation if available. But if those options don’t materialize, bringing back Clay Holmes could be the practical move.
Holmes already has a place in the mix after Chicago traded top prospect Jefferson Rojas to get him. Re-signing him would give the Cubs a reliable fifth starter or a useful long reliever and sixth option on a club built to contend.
He also brings playoff experience, and that matters for a team with championship expectations. In 2026, Holmes went 6-8 with a 3.29 ERA and 78 strikeouts.
The outfield presents its own uncertainty, with Ian Happ and Seiya Suzuki both set to become free agents. If the Cubs choose to keep their focus on pitching and hunt for value elsewhere, Taylor Ward is the kind of bat who could fit.
Ward can handle both corner-outfield spots and offers some power, but what makes him interesting is the balance he brings. He struggled last year, hitting .225 with 7 home runs and 37 RBI’s, which should keep the price down.
Even so, his discipline at the plate stands out, and his ability to draw walks and create traffic on the bases could help a Cubs lineup that is already among the league’s best. He wouldn’t need to be the main attraction.
He could be the steady piece who gives the offense another way to keep pressure on opposing pitching.
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Cubs Face A Catcher Decision That Could Hurt More Than Expected
The upcoming catcher market already looks like one of the more complicated parts of the Cubs offseason, and Carson Kelly sits right in the middle of it. The class includes more familiar names such as Tyler Stephenson and Ryan Jeffers, but the way teams value catchers often lags behind what they actually do behind the plate, which is why this conversation could matter more in Chicago than it might elsewhere.
From the Cubs standpoint, the question is not just who is available, but who fits best if they decide to reset the position again. Kellys profile makes the whole discussion a little trickier than it first appears, and with the market taking shape around age, recent production and contract expectations, the Cubs may end up facing a decision that is harder to navigate than the rankings suggest. [Read more 🡒]