The Cubs are headed into another offseason with the same familiar problem hanging over everything: they need more impact, especially on the mound and in the lineup. While the Dodgers and Brewers keep playing into the NLCS, Chicago is back at home trying to figure out which playoff performers might actually be within reach for Jed Hoyer and company.
Not every name in October baseball is realistic for the Cubs, of course. Shohei Ohtani isn’t part of this conversation, and neither is anyone else who would be completely out of range. The focus here is on players who could reasonably become available through free agency or the trade market, and who might fit what Chicago is trying to fix.
Tarik Skubal is the cleanest fit on paper. The Cubs need pitching, but more than that, they need real quality pitching, and Skubal stands out as the top arm likely available in free agency.
He would solve a major problem in one move. The issue is obvious: he’s going to command what would be the biggest contract in Cubs history, which makes Chicago feel like a long shot.
A return to Los Angeles also sounds like the likeliest outcome.
There are far fewer realistic targets coming out of Milwaukee, and that’s before you factor in how unlikely it is the Brewers would want to help the Cubs. Still, Dustin May is a name worth tracking.
Milwaukee acquired him at the deadline, and he has a mutual option for 2027. Those deals usually get declined, so the 29-year-old should be available this offseason.
He’s not the headline answer, but his velocity is the kind of thing Chicago’s rotation could use, and he profiles as a fallback option if the Cubs miss on bigger names.
Nick Martinez is another pitcher who fits the broader need. Some people might have expected Freddy Peralta’s name here, and sure, the Cubs will likely be tied to him this winter.
But his contract demands may well be too rich for their taste. Martinez, on the other hand, looks like a much more believable target.
He turned in a 3.10 ERA in 31 starts for the Rays in 2026 and already knows the NL Central. He wouldn’t exactly represent a dramatic change in how the Cubs have approached pitching additions lately, but he’s a sensible option.
If the Cubs end up looking for help in the outfield, Randall Grichuk deserves a look. The ideal outcome would be bringing back Tyrone Taylor, since he gave Chicago the kind of fourth-outfielder value that matters - especially with his success against left-handed pitching.
If Taylor isn’t back, Grichuk becomes an appealing alternative after reviving his career with the White Sox this season. Against lefties, he posted a wRC+ of 181.
Steven Kwan is the biggest offensive swing on the list, and the Cubs have already been linked to him. It’s still unclear whether the Guardians would actually move him, but if they do, he checks a lot of boxes for Chicago. He brings a contact-heavy approach at the plate and is a regular Gold Glove candidate in the outfield, which makes him the kind of upgrade the Cubs should be chasing if the opportunity opens up.
In Other News...
Cubs Seem Ready To Move On From Shota Imanaga
Shota Imanaga finished September with a 2.25 ERA, but his 2026 season still ended with a cloud hanging over his future in Chicago. The Cubs never got a postseason look at him because of their early exit, and even before that, the franchises posture suggested a bigger question than any one outing. Beat writer Patrick Mooney has indicated the organization may be ready to move on this winter, with the clubs decision to decline Imanagas three-year option standing out as the clearest sign of hesitation.
Imanagas rookie year gave the Cubs plenty of reasons to believe they had found a durable front-line arm, but the follow-up was far less tidy. He gave up 35 home runs in 2026, the second-most in MLB, and the inconsistency has fueled the sense that trust inside the organization has eroded. For a team still trying to build around reliable pitching, the issue is no longer just whether Imanaga can flash again, but whether the Cubs still view him as part of what comes next. [Read more 🡒]
Cubs Offseason Pitching Plan Is Starting To Make Real Sense
The Cubs offseason is starting to look a lot less abstract and a lot more focused, with pitching clearly at the center of whatever comes next. Chicago is expected to make a meaningful overhaul on the mound, and the logic behind it is easy to see after a season in which the rotation never felt fully settled. With several current arms carrying uncertainty into the winter, the front office has a clear area to address if it wants to stabilize the roster.
Michael King has emerged as the kind of target that fits the assignment, giving the Cubs a realistic option if he reaches free agency after this year. He brings the kind of recent performance teams can build around, including a strong regular season and a postseason run that only added to his appeal. The only real question now is how aggressive Chicago wants to be in turning that fit into a signing, especially with more than one rotation spot still in flux. [Read more 🡒]
Cubs Pitching Reset Could Hinge On One Rare International Arm
The Cubs are staring at another offseason pitching overhaul, with a long list of arms either headed for free agency or reaching option decisions. For a staff that needs help in several places, that has put a premium on finding pitching outside the usual domestic market, and Kaima Taira has quickly emerged as one of the more intriguing names to watch.
A rare international left-hander with a strong track record in Japan, Taira is viewed as a potential fit for Chicagos needs at just the right time. If he is posted when expected in early November, the Cubs and every other interested club will have only a short window to make their case before the lockout interrupts the market, turning his availability into one of the more important early tests of the winter. [Read more 🡒]