ST PETERSBURG, FLORIDA – OCTOBER 28: Dustin May #21 of the Milwaukee Brewers celebrates with teammates in the locker room after defeating the Tampa Bay Rays in the 2026 World Series at Tropicana Field on October 28, 2026 in St Petersburg, Florida. (Photo by Carmen Mandato/Getty Images)

Dustin May celebrates during 2026 World Series. Getty
The Chicago Cubs couldn’t solve their pitching in 2026. Injuries and ineffectiveness couldn’t even be solved by mid-season trades.
Chicago still made the playoffs, but they weren’t even the top team in the NL Central Division. That, of course, was the Milwaukee Brewers, who won the World Series.
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The Cubs would love to get back into the mix near the top of the division with the Brewers, but to do so, pitching is going to have to go better for them in 2027.
Some of that will come from luck. They’ll have a few of their arms back, but they actually need to keep them on the mound.
Adding depth could be crucial, too, because it was obvious in 2026 that the Cubs — like any team would — will struggle if pressed to go too deep into their pitching staff.
A name has surfaced, though, who could help: Dustin May.
Cubs Dustin May Update

GettyST PETERSBURG, FLORIDA – OCTOBER 28: Dustin May #21 of the Milwaukee Brewers celebrates with teammates in the locker room after defeating the Tampa Bay Rays in the 2026 World Series at Tropicana Field on October 28, 2026 in St Petersburg, Florida. (Photo by Carmen Mandato/Getty Images)
The Athletic’s Jim Bowden posted a report on Sunday on X to suggest that a lot of teams are all going after May. The Cubs are one of them.
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Bowden wrote this: “The market for Dustin May is blowing up right now with the Cubs, Nationals, Orioles, Giants, Reds, Guardians, Marlins, White Sox and Blue Jays all in play right now!!!”
Three exclamation points certainly suggest a situation that is heating up in a hurry.
Given that the lockout will hit on Dec. 1, it wouldn’t be a shock to see May get his negotiations done and sign before them.
The Cubs clearly have a lot of competition, including their cross-town Chicago rival White Sox.
But at least the Cubs are in the mix, which is a positive thing.
How Good is Dustin May?

GettyMILWAUKEE, WISCONSIN – OCTOBER 24: Dustin May #21 of the Milwaukee Brewers celebrates an out against the Tampa Bay Rays during the fifth inning in game two of the 2026 World Series at American Family Field on October 24, 2026 in Milwaukee, Wisconsin. (Photo by Michael Reaves/Getty Images)
The Athletic’s Eno Sarris recently wrote about how May might fly under the radar but actually has very good stuff.
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“There are two domestic free agents who will be under 30 years old next season and have above-average stuff and command as judged by Stuff+ and Location+,” Sarris writes, referring to a couple of his metrics for measuring pitch performance. “One is Trevor Rogers, and he’s projected to get a nine-figure deal in most spots. The other is Dustin May, who likely won’t get half that. There are also some interesting changes May made last year that didn’t show up in the ERA but could be intriguing. For one, he got his arm angle back up to where it was years ago when he was a top prospect with the Dodgers. That improved the vertical movement on his cutter and four seamer, which, in turn, allowed him to focus on the four-seamer, cutter and curveball more versus lefties. Results on the field matter, too, so this isn’t an argument that May should get the same money as Rogers. But May is more interesting than his ERA over the last two years.”
The key point to consider with May is that his traditional numbers may not tell the whole story. There’s definitely potential to be tapped into with May if the Cubs can land him.
This article was originally published on HEAVY
The post Cubs Get Loaded Dustin May Free Agent Update appeared first on HEAVY.
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