The Chicago Cubs will need some pitching help this offseason. 

The Cubs currently have six starters who could leave in free agency this winter. Clay Holmes, Kevin Gausman, Shota Imanaga, Matthew Boyd, David Peterson, and Colin Rea could all find new homes in the coming weeks/months. 

Those key departures mean the Cubs will have to be aggressive in free agency to replace those starters. Here are three starters who make sense for the Cubs to go after this winter. 

Freddy Peralta is one of the most coveted starters in this year’s free-agent cycle. Although he struggled with the New York Mets at the start of the 2026 season, Peralta raised his stock after a strong second half with the Tampa Bay Rays. 

The two-time All-Star posted a 3.25 ERA, 1.012 WHIP, and 43 strikeouts over 55 ⅓ innings pitched with the Rays. That’s the type of pitcher the Cubs could acquire at the top of their rotation for 2027 and beyond. 

Chicago is obviously very familiar with Peralta from his time with the Brewers. Manager Craig Counsell also spent six seasons with the right-hander in Milwaukee from 2018 to 2023. The team’s familiarity with him and his status as a high-end starter make him a potential target this winter. 

The Cubs saw firsthand in the playoffs how good Michael King can be. King threw seven shutout innings with one hit, three walks, and eight strikeouts against the North Siders in Game 1 of the National League Wild Card Round. 

King would obviously be a solid get for the Cubs this offseason. He has posted strong pitching numbers in each of his three seasons since becoming a full-time starter. The veteran right-hander has posted a combined 3.15 ERA over those three years. 

In 2026, King finished with a 3.21 ERA, 1.178 WHIP, and 159 strikeouts over 185 innings pitched. With an 89th-percentile Breaking Run Value and a 98th-percentile Offspeed Run Value, the 31-year-old has real potential at the top of the Cubs’ rotation.

Clay Holmes and the Cubs are really a match made in heaven. Holmes is an extreme groundball pitcher who ranked in the 99th percentile in groundball rate this past season. That should play well with an infield that features three former Gold Glove winners (Dansby Swanson, Alex Bregman, and Nico Hoerner). 

Holmes was obviously a part of this Cubs team this past season after Chicago traded for him at the deadline. While his overall results weren’t elite (4.25 ERA across 48 ⅔ innings), the two-time All-Star had some encouraging outings down the stretch. 

The Cubs could look to re-sign Holmes this offseason.