Cubs may be ignoring what the Brewers already learned about Dustin May

It was a quiet GM Meetings for the Chicago Cubs, considering it was more about who the Cubs likely won't be bidding for this offseason, instead of who the team has expressed interest in. Though, one name that has emerged as being someone the Cubs have on their radar is former Milwaukee Brewers starting pitcher Dustin May.

May, of course, was drafted by the Los Angeles Dodgers in 2016, and flashed signs of becoming a fixture in their rotation during the early years of his career. The Dodgers becoming the Dodgers and May having a checkered injury history essentially forced him out of the picture in LA, leading to a trade to the Boston Red Sox ahead of the 2025 season.

May made his way to the St. Louis Cardinals to open the 2026 campaign, and was traded to the Brewers at the deadline. May has always had a fastball that has enticed teams, and there was some thinking that Milwaukee would finally be the team to unlock a consistent level of success. Instead, he posted an ERA of 5.65 across 10 starts with the Brewers, and was ultimately factored out of the rotation plans during their World Series run.

Still, May is drawing early interest this offseason, and the Cubs are among the teams talking to the World Series champion.

Cubs’ interest in Dustin May raises an uncomfortable Brewers question

Yes, it's somewhat comical that the Cubs think they can do what the Brewers couldn't in unlocking success for May, but it also speaks to the problem that Chicago is facing this offseason.

With the goal of adding three established starting pitchers to their rotation before the start of the 2027 season, the sense is that the Cubs may be going for a quantity over quality approach. Along those lines, May would fine as a the third and final addition to the Cubs' rotation this offseason. It would be similar to what to expect from Edward Cabrera moving forward in that the Cubs can't expect May to be an answer, but if things work out, he could be a surprise development to their success in 2027.

Two things to note with May, his fastball velocity sits in the 85th percentile, according to Baseball Savant, and his extension is in the 72nd percentile. That's where the appeal lies, and suggests that with the right tweaking, May could have sustainable success. May would be a fun project for the Cubs, but there would have to be more done if the offseason was going to be considered a win for Jed Hoyer and the front office.

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