Cubs could take a familiar Jed Hoyer gamble on Dustin May but it can't be their only move

When Dustin May was forced out of the pitching plans for the Los Angeles Dodgers, it felt like the Chicago Cubs should have been among the teams to take a flier on the former third-round pick. Instead, he was traded to the Boston Red Sox and spent the 2026 season with the St. Louis Cardinals and Milwaukee Brewers. A free agent this offseason, it seems inevitable that the Cubs will be mentioned as a potential suitor.

To be clear from the jump, May certainly can't be the primary addition to the Cubs' rotation this offseason. He's more of a project than an expectation, but in a scenario where the Cubs have already added a big-ticket arm to their rotation, and perhaps one more established option, May feels like a worthwhile project for Jed Hoyer and Co.

The knock on May in recent years is that he's been chasing the success he had in his early years with the Dodgers. There was moment with the Cardinals early in the year that it looked like it was starting to click, but he still had an ERA of 4.38 in his 21 starts before the trade. With the Brewers, he's posted an ERA of 5.65 in 10.

Dustin May feels like a classic Jed Hoyer project (but Cubs can't stop there)

What likely would intrigue the Cubs is May's fastball. It's the type of fastball they work, and easily his best pitch. His fastball during the 2026 season sat in the 82 percentile in terms of run value, and it sits in the upper 90s. It's the type of velocity the Cubs have lacked in their rotation, and if they can get him back to keeping the ball on the ground often, as he was doing at the start of his career, there's reason to believe it could be an ideal flier for the team to take.

In a scenario where the Cubs sign someone like Michael King, perhaps bring back both Clay Holmes and David Peterson, rounding out the offseason focus on pitching with the signing of May would be a significant stride forward for the pitching staff as a whole. That also goes to show that May, in a vacuum, wouldn't be the right move for the Cubs, but as part of several moves to address the rotation, could work.

It's the reality the Cubs are in, considering there's no telling what version of Justin Steele they will have when he takes the mound in 2027. Not to mention, Cade Horton will miss most, if not, all of the season, and Ben Brown's neck injury could prevent him from being in the rotation full-time. As well as Edward Cabrera potentially being a miss.

Before the Cubs even consider May, they will need to add expected results to the rotation. Then, Hoyer will have room for some projects.

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