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Cardinals Face Major Obstacle in Potential Dustin May Reunion

The St. Louis Cardinals need another hurler and a familiar face is out there for the taking.

Aug 30, 2026; Milwaukee, Wisconsin, USA; Milwaukee Brewers pitcher Dustin May (21) throws a pitch in the first inning against the Texas Rangers at American Family Field. Mandatory Credit: Benny Sieu-Imagn Images | IMAGN IMAGES via Reuters Connect

There are some question marks looming over the St. Louis Cardinals right now ahead of the 2027 Major League Baseball season.

Right now, there are three hurlers that seem like locks in the rotation: Kyle Leahy, Michael McGreevy and Andre Pallante. Quinn Mathews showed down the stretch that he can positively impact a big league rotation and very well could join the group right out of the gate in 2027. Matthew Liberatore is another option, but he's certainly up in the air after a brutal 2026 season. There are prospects on the way to help, but the Brewers need one more veteran to round out this group. There has been speculation and rumors about potential options, including reuniting with Dustin May, who was traded to the Milwaukee Brewers ahead of the trade deadline.

On Monday, Derrick Goold of the St. Louis Post-Dispatch weighed in on the idea of a reunion, including an obstacle that could prevent it from happening.

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

Dustin May Reunion Should Be In Cards For St. Louis

Oct 27, 2026; St. Petersburg, Florida, USA; Milwaukee Brewers pitcher Dustin May (21) walks back to the dugout after pitching against the Tampa Bay Rays during the first inning in game four of the 2026 World Series at Tropicana Field. Mandatory Credit: Kim Klement Neitzel-Imagn Images | IMAGN IMAGES via Reuters Connect

A multi-year deal clear doesn't appear in the cards at the moment, per Goold. If things change, the Cardinals should absolutely call.

Last offseason, the Cardinals signed May to a one-year deal with a mutual option for the 2027 season. While in St. Louis, May made 21 appearances and logged a 4.38 ERA and a 106-to-35 strikeout-to-walk ratio in 109 innings pitched. In his 21 starts, he gave the Cardinals a chance to win in the vast majority of the contests he pitched in. He allowed more than four runs five times in a Cardinals uniform.

If May has to settle for a short-term deal once again, it would be great if it were in St. Louis. The partnership worked. He gave the Cardinals a chance to win games and then was traded in a package with JoJo Romero to bring two elite prospects to town in No. 5 prospect Alexander Frias and No. 11 prospect Josiah Ragsdale.

The Cardinals' payroll is low and St. Louis should absolutely bring someone in. May is out there for the taking again. It worked out the first time. If his market doesn't develop to the point of a lucrative multi-year deal, St. Louis should scoop him up.

If not May, then other options who should be the Cardinals' radar are veterans like Shane Bieber, Nick Martinez, Casey Mize, Kevin Gausman, Jack Flaherty, Kris Bubic or even Michael King,

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