Dustin May Linked To Cubs As Rotation Option

Especially in the front half of the 2027 season, the Chicago Cubs are in need of depth in their starting rotation.

While any warm body will be connected to the Cubs in free agency, there are certain starters that make more sense. Enter Dustin May. The right-hander, who spent the 2026 season with the St. Louis Cardinals and World Series champion Milwaukee Brewers, is one option the Cubs have been connected to by MLB Network's Jon Morosi. Morosi also cited the Chicago White Sox, San Diego Padres and Houston Astros as other teams interested in May.

The 29-year-old May had a decent bounce-back season after having Tommy John revision surgery in 2024 and having the usual bumps in 2025 as he was traded by the Los Angeles Dodgers to the Boston Red Sox during the season.

You have to look a little deeper at May's numbers to see his effectiveness. He had a 3.63 FIP (4.70 ERA) with an 8.1% walk rate and 23.2% strikeout rate between the Cardinals and Brewers. He signed a one-year, $12.5 million deal with the Cardinals last offseason, hoping to use 2026 as a platform for a bigger contract.

The Cubs currently list two players in their starting rotation in right-handers Ben Brown and Cade Horton. Brown just underwent a neck surgery and is expected to return midseason, while Horton had Tommy John surgery in April, putting him on a similar return timeline.