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What a Cardinals, Dustin May Reunion Would Look Like

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World Series: Milwaukee Brewers v Tampa Bay Rays - Game Four
ST PETERSBURG, FLORIDA - OCTOBER 27: Dustin May #21 of the Milwaukee Brewers reacts during the third inning against the Tampa Bay Rays in game four of the 2026 World Series at Tropicana Field on October 27, 2026 in St Petersburg, Florida. (Photo by Carmen Mandato/Getty Images)

The St. Louis Cardinals have some work to do before the lockout. The team is not gearing up to be a contending club in 2027, but they do have some holes they can fill to make the team better. At the trade deadline, they shipped Dustin May to the eventual World Series champion Milwaukee Brewers for two outfield prospects to strengthen their farm system.

May was brought in as a starter looking to rebuild his value and return to free agency hoping for a better contract. With free agency underway, the Cardinals can now potentially bring May back on a short-term deal. Derrick Goold of the St. Louis Post-Dispatch notes that it’s possible, but that it has to come under certain conditions.

“He maintains a favorable view of the Cardinals and their pitching support structure,” Goold wrote. “But the right-hander will first see if there is a multi-year offer, and that’s unlikely to come from the Cardinals.”

The One Way St. Louis Cardinals Can Reunite With Dustin May

May is likely looking for a multi-year deal. Since the Cardinals are rebuilding, that is not likely to happen for them. But it doesn’t mean that the Cardinals won’t be able to bring him back. They’ll just have to wait and see if other teams give May multi-year offers and if he ultimately likes them or not. If he doesn’t get what he desires, then he could return to St. Louis for one more year.

However, that will likely come later in the offseason, and potentially even after the lockout, which could be a while, so if that’s the case, the Cardinals will need to choose another starter looking to rebound and sign a one-year deal to rebuild lost value.

Goold named a few that could work out for St. Louis.

“Right-hander Casey Mize is arguably the next best short-term upside play,” Goold wrote. “Shane Bieber and two pitchers with past Cardinals ties, Jack Flaherty and Zac Gallen, are other starters looking for rebound opportunities.”

Who Makes the Most Sense?

All four options listed by Goold would be good fits, but out of them all, Shane Bieber would likely make the most sense because he is a former Cy Young winner. At a pitcher friendly place like Busch Stadium, Bieber could rediscover his potential and possibly return to his old form in a lower-pressure environment.

But it doesn’t seem likely that May will return to the Cardinals. Again, it’s not impossible, but the Cardinals aren’t likely to give him the deal he will be looking for, so fans should not get their hopes up for a reunion.

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