The Chicago Cubs are expected to be very active this offseason. 

Part of that is because the Cubs could lose several free agents this winter. Players like Kevin Gausman, Shota Imanaga, Matthew Boyd, Clay Holmes, Ian Happ, Seiya Suzuki, and Carson Kelly could all depart in the coming months. 

That will force the Cubs to be active in the free-agent market to replace them. In Jim Bowden’s recent article at The Athletic on the top-40 free agents this offseason, Bowden lists the Cubs as the best fit for three outside free agents. 

The Cubs had multiple opportunities to trade for Freddy Peralta this past season. The Milwaukee Brewers traded him to the New York Mets in the winter, and then the Mets shipped him off to Tampa Bay to finish the season with the Rays. 

Peralta will now head to free agency looking for a big contract. It was a tale of two seasons for the All-Star pitcher. He posted a 4.99 ERA over 113 ⅔ innings with the Mets and a 3.25 ERA over 55 ⅓ innings with the Rays to end the regular season. 

Chicago is obviously very familiar with Peralta from his time in Milwaukee. Manager Craig Counsell managed the right-hander for multiple seasons with the Brewers, and Peralta would fill that top-of-the-rotation starting pitcher need. Bowden lists the Cubs, Padres, and White Sox as the best fits. 

The Cubs will need to replace several pitchers on their roster for next season, especially if Imanaga, Gausman, Holmes, and Boyd all leave. A pitcher like Foster Griffin could make a lot of sense for the North Siders as a free-agent pickup this offseason. 

Griffin won’t cost as much as some of the other high-level available starting pitchers. Bowden lists the southpaw’s expected contract at just three years, $67 million. That feels like the appropriate price point for a pitcher who would be a solid No. 3 starter in a rotation. 

After spending several years overseas in Japan, Griffin posted a 3.60 ERA and a 1.210 WHIP across 172 ⅔ innings in his first season back in the big leagues. He would be a solid pickup for the Cubs, and Bowden lists the North Siders, Pirates and White Sox as the best fits. 

There’s a strong possibility that Kelly leaves this offseason. That means the Cubs will have to replace him at the catcher position. Bowden believes Tyler Stephenson could be a solid replacement for Kelly if he leaves Chicago. 

Stephenson has posted solid all-around numbers over the past three seasons. He hit .258 with 19 home runs and 66 RBI in 2024, hit .231 with 13 home runs and 50 RBI in 2025, and hit .241 with 15 home runs and 54 RBI in 2026. 

Stephenson is one of the best catchers available in this year’s free agent class. Bowden lists the Cubs, Reds, Rangers, and Angels as potential fits for the veteran backstopper.