Given his always-loud stuff, the fact that he still falls into that category of pitcher who hasn’t broken out and thus isn’t going to cost the moon, and the fact that he couldn’t be given a Qualifying Offer, I expected Dustin May to be connected to the Chicago Cubs at some point.
And since it was Lance Brozdowski who did the connecting, I thought it worth sharing:
I have no specific intel here, but I’m connecting the dots on a few things… Abreu+Yankees – good with mechanics; will value his SL highly Bubic+Rays – injury tolerance May+Cubs – big spin with velo, need to fill ~3 SP spots, won’t be > $20m AAV
— Lance Brozdowski (@LanceBroz) November 10, 2026In other words there, Lance is not saying he’s heard anything about this. He’s just connecting the same dots we might connect, and rightly pointing out that the Cubs *NEED* three starting pitchers. They’re not all three gonna be first or second tier types.
Dustin May, who only just turned 29, was a long-time Dodgers prospect and young starter, dripping with talent but unable to stay healthy and part of the big league rotation. Eventually, the Dodgers sent him to the Red Sox in 2025, and then he signed with the Cardinals this past offseason. The Cardinals flipped him at the deadline to the Brewers, where his season continued to feature strong peripherals and meh results.
(via FanGraphs)May doesn’t necessarily have the pitch profiles the Cubs look for, but he does miss bats when he’s at his best, and he does have a history of strong groundball rates before the last two seasons. He also throws a wide variety of pitches, and the Cubs may appreciate having that foundation with which to work off of.
The combination of great fastball velocity and extension means he gets on batters quickly, but, as you can see, they still hit him very hard all year:
(via Baseball Savant)Despite the meh results and the very loud contact, you can safely assume the price tag on Dustin May wouldn’t actually be THAT cheap, given that he’s just 29 and he’s got that elite starter velocity. Those things are both very expensive in free agency, almost regardless of anything else, because they are rarely acquired for only money. The projections tend to be in the two or three-year range, with AAVs around $15 to $18 million. Not so much that they’re breaking anyone’s bank, but enough that it stings to absorb if he winds up getting hurt again or performing as a below-average number four.
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