Former Cardinals Starter Pitched as Reunion Candidate for 2027

World Series: Tampa Bay Rays v Milwaukee Brewers - Game Two
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MILWAUKEE, 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 St. Louis Cardinals have made some very important strides in a short amount of time. The team was actually in postseason contention for much of the season and was not eliminated until the final week. But there are still going to be some holes to fill for the 2027 team. The bullpen needs work, and they could certainly use a veteran starter as well.

The Cardinals had Dustin May on the roster before the trade deadline, and sent him to the Milwaukee Brewers, who are now just two wins shy of their first World Series title in franchise history.

Will Leitch of MLB.com listed five veteran starters that could be fits for the Cardinals in 2027, and among them was indeed May.

“Up for another go-around? May improved his value with what he did for the Cardinals, as evidenced by how much they got for him in their trade. But he struggled after moving to Milwaukee — pending the World Series — and it’s clear he’s not the No. 3 postseason starter the Brewers were hoping for,” Leitch wrote.

“May still has a lively fastball and is relatively young compared to the market, as he won’t turn 30 until next September. You could argue that he still has a bit more to prove, and perhaps a return to St. Louis could help both parties once again.”

Dustin May Reunion Pitched for St. Louis Cardinals

May finished the regular season with a 7-9 record and a 4.70 ERA in 31 starts. For the first time in several years, he was healthy for the full season, but he wasn’t quite what the Brewers were expecting.

However, he posted solid numbers in St. Louis, going 5-7 with a 4.38 ERA in 21 starts. Because he has struggled in Milwaukee a bit, this could leave the door open for a reunion with St. Louis. May spoke highly of his time with the Cardinals and enjoyed being a veteran leader for a young starting rotation. Having that presence likely contributed to the success of St. Louis’ rotation in the first half, and bringing him back would certainly benefit a team looking to take the next step in their rebuild.

May has bounced back from several injuries and has become a dependable starter again, even though his numbers in Milwaukee weren’t quite where he wanted them to be, and as Leitch notes, he won’t be 30 years old until next September, so he is still relatively young and does have a lot of upside.

What Would a Dustin May-Cardinals Reunion Look Like?

The only question remaining would be what a contract looks like. He has a mutual option for next year, but the Brewers will likely decline it, leaving the door open for a reunion in St. Louis.

He could sign a similar deal with the Cardinals with an option for 2028, or perhaps even sign a multi-year contract with opt-outs sprinkled in between each year. Based on his performance, he could then make the decision on whether to stay or leave after each year.

We’ll see if the Cardinals decide to pursue him again.

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Former Cardinals Starter Pitched as Reunion Candidate for 2027

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