The Chicago Cubs are facing a gargantuan task this offseason.
First, they’re going to have to rebuild their entire starting rotation. The whole end-of-season rotation (Matthew Boyd, Shota Imanaga, Kevin Gausman, Clay Holmes, David Peterson) could be gone via free agency. Cade Horton will miss most—if not all—of 2027 recovering from Tommy John surgery. Justin Steele has missed almost two full seasons due to his own elbow surgery issues. Meanwhile, new Cub Edward Cabrera will have to rebound from an awful 2026 filled with injury and underachievement.
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The team also needs a dominant and consistent closer to help close out games.
Then, on the position player front, the Cubs are facing the likely loss of right fielder Seiya Suzuki, left fielder Ian Happ, and catcher Carson Kelly to free agency, as well as outfield assets Michael Conforto and Tyrone Taylor.
It’s probably not realistic to expect Chicago to fill all its needs with free agent purchases—especially with a weak free agent talent pool this offseason and a looming lockout.
Although there remains the possibility that the front office could make moves to retain at least a couple high-end assets with extensions, it’s more likely that the team will lean on trades to fill holes and patch up weak spots.
The Cubs’ tradeable assets
Knoxville Smokies pitcher Jaxon Wiggins (41) pitches during a minor league baseball game between the Knoxville Smokies and Chattanooga Lookouts at Covenant Health Park in Knoxville, Tenn., on June 3, 2025.
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But what does the Cubs’ farm system have left to trade?
Chicago traded away its top prospect Owen Caissie last offseason in the Edward Cabrera trade with the Marlins and they dealt the highly-regarded Jefferson Rojas to the Mets at the trade deadline for Clay Holmes and Tyrone Taylor. Over the course of the season, they also traded young assets Moises Ballesteros, Jonathon Long, Mason McGwire, and Brett Bateman, among others.
Offhand, it doesn’t look like the Cubs have much in their farm system that they would want to trade. The outfield prospect trio of Josiah Hartshown, Kane Kepley, and Ethan Conrad make up three of their top five overall prospects and will be counted on to be at least two-thirds of the team’s future outfield.
Jaxon Wiggins has tremendous upside, but had an injury-plagued 2026 that lowered his prospects status considerably. Even with his reduced shine, though, the Cubs may not be willing to part with any homegrown pitching talent at this point.
Catcher Owen Ayers is another valuable prospect, but the Cubs may see him as their catcher of the future and an indispensable asset with Kelly possibly leaving the team this offseason.
Realistic trade bait
Apr 5, 2026; Cleveland, Ohio, USA; Chicago Cubs right fielder Matt Shaw (6) celebrates his solo home run in the third inning against the Cleveland Guardians at Progressive Field. Mandatory Credit: David Richard-Imagn Images
So, who’s left to trade?
Outfielder Kevin Alcantara and pitcher Jordan Wicks have major league jobs waiting for them if they can turn the corner on their development. But both may also find themselves on the trade block because they’re out of minor league options and Chicago will be hitting a “roster them or lose them” wall if they can’t earn a major league roster spot this coming spring.
Then, of course, there’s young major league talent Matt Shaw and Pedro Ramirez, who factor into the Cubs’ 2027 plans, but may have more worth as trade bait.
In a perfect world, the Cubs would like to hold on to Shaw and Ramirez as they may factor into their outfield plans for the coming season, as well as continue their roles as valuable bench talent.
The path for the 2027 Cubs, however, is far from a perfect world scenario. The team may be finding itself in a spot where they must make some very uncomfortable trades—including those involving top prospects—if they want to take advantage of their window of opportunity to bring home a championship.
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