The Cubs were active in the trade market this past summer, adding multiple starting pitchers to help fill out an injury-depleted rotation. Now, the Cubs will likely need to do a lot more work to fill out the 2027 rotation, as several notable faces will either be unavailable or are not even on the roster anymore.

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When the 2026 season ended, that meant that Matthew Boyd, Clay Holmes, Kevin Gausman, and Shota Imanaga all went to free agency. Additionally, one should also remember that Cade Horton, who missed virtually all of 2026 thanks to UCL reconstruction surgery, likely won’t be ready for whenever the 2027 season ultimately begins.

So, where does that leave the Cubs’ rotation for 2027?

Chicago does have Edward Cabrera, plus Javier Assad and Ben Brown. Brown, who fine-tuned his pitch arsenal, finally had that big year in 2026, albeit an injury-shortened one. There’s also Justin Steele, who rehabbed down in the Minors later in the year but ultimately didn’t pitch in an MLB game.

With all of that in mind, it would make a lot of sense for the Cubs to land one of the top starting pitchers available this winter. But the rotation is not the only area of weakness.

Chicago lost Carson Kelly to free agency. Kelly was a good add for the Cubs, and he worked well in a tandem with Miguel Amaya. Adding a depth catcher would make a lot of sense, even if it wound up being just a stopgap for Owen Ayers.

But what’s also more pressing is a need to add at least one outfielder this winter. Ian Happ and Seiya Suzuki, both 20+ home run hitters for the Cubs last season, went to free agency.

It would make sense if utilityman Matt Shaw, who does have some outfield experience now, worked his way into a regular role. The Cubs also have Justin Dean and Kevin Alcantara, the latter of whom is running short on chances, on the 40-man roster.

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