Cardinals Homecoming? St. Louis Floated for 2027 Rotation Reunion

The St. Louis Cardinals need a boost in the starting rotation and an old friend is likely to be available.

Oct 24, 2026; Milwaukee, Wisconsin, USA; Milwaukee Brewers pitcher Dustin May (21) throws a pitch against the Tampa Bay Rays during the fifth inning in game two of the 2026 World Series at American Family Field. Mandatory Credit: Benny Sieu-Imagn Images | IMAGN IMAGES via Reuters Connect

The St. Louis Cardinals made the right decision by selling off pieces ahead of the 2026 Major League Baseball trade deadline.

At the time, the Cardinals were not out of the mix in the race for a playoff spot, to say the least. But, still, it was the right call. St. Louis is still in a rebuilding phase under president of baseball operations Chaim Bloom and the Cardinals added a handful of intriguing prospects, including No. 5 prospect Alexander Frias and No. 11 prospect Josiah Ragsdale. Both came over in the Cardinals' trade with the Milwaukee Brewers this past summer that sent Dustin May and JoJo Romero to the National League Central champs.

This winter, May is likely to enter free agency again. He has a mutual option that almost surely will be declined. The Cardinals need a veteran starter. May is likely to be available. MLB.com's Will Leitch made an intriguing pitch that both sides should consider.

The Cardinals Should Target Dustin May

Oct 24, 2026; Milwaukee, Wisconsin, USA; Milwaukee Brewers pitcher Dustin May (21) pitches during the fifth inning against the Tampa Bay Rays in game two of the 2026 World Series at American Family Field. Mandatory Credit: Michael McLoone-Imagn Images | IMAGN IMAGES via Reuters Connect

"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," Leitch wrote.

This isn't the first time that May has been floated as a reunion candidate for St. Louis. Frankly, the idea makes a lot of sense. With the Cardinals, May logged a 4.38 ERA in 21 starts to go along with a 106-to-35 strikeout-to-walk ratio in 109 innings pitched. Injuries were the story of May's career from 2021 through the 2025 season. The Cardinals kept him healthy and he flashed the talent that led to his breakout years ago as a member of the Los Angeles Dodgers. Since landing with the Brewers, he hasn't been as successful. He had a 5.65 ERA in 10 starts in the regular season. He has a 5.63 ERA in the playoffs in four appearances, including one start.

May hasn't been great down the stretch with the Brewers, but he has stayed healthy. He shouldn't be exceptionally expensive this winter and the Cardinals have a real need for another starter. Last winter, the Cardinals gave May a one-year, $12.5 million deal with a $20 million mutual option. After recording a 4.70 ERA in the playoffs in 31 starts, a contract in the same price range should be realistic.

If the Cardinals were to struggle in 2027 in the standings, they could simply follow the same playbook they used in 2026 and try to flip May ahead of the trade deadline. May was a great addition for the Cardinals in 2026. He helped on the hill and helped to bring back two elite prospects. This winter, there's no reason not to call May and see if he's interested in coming back.