Will Cardinals Continue Their Dustin May-esque Trend This Offseason?

After a solid start to the season, the St. Louis Cardinals traded May to the Milwaukee Brewers to bolster their farm system.

Sep 22, 2026; Philadelphia, Pennsylvania, USA; Milwaukee Brewers pitcher Dustin May (21) throws a pitch during the first inning against the Philadelphia Phillies at Citizens Bank Park. Mandatory Credit: Eric Hartline-Imagn Images | IMAGN IMAGES via Reuters Connect

The St. Louis Cardinals had a surprisingly successful season, but what's even better is how the team's future looks far more solidified than it did at this point last year.

Despite falling short of the postseason and posting a losing record for the second straight year, the Cardinals should be content with how they performed this season. St. Louis was in the playoff race for most of the season, and players like JJ Wetherholt, Jordan Walker and Alec Burleson have solidified themselves as key foundational pieces moving forward.

Though the Cardinals appear to be ahead of schedule in their rebuild, they are still likely a couple of years away from truly being contenders. With that in mind, instead of trying to bolster their starting rotation with a star player, will St. Louis continue the offseason trend of signing free-agent pitchers with upside to short-term contracts, as they did with Dustin May this year?

May was a solid addition for the Cardinals

Aug 26, 2026; New York City, New York, USA; Milwaukee Brewers catcher William Contreras (24) and starting pitcher Dustin May (21) walk the field in the game against the New York Mets at Citi Field. Mandatory Credit: Wendell Cruz-Imagn Images | IMAGN IMAGES via Reuters Connect

"The Cardinals didn’t make many additions heading into the 2026 season, but the biggest one they did make turned out to be an unqualified success," MLB.com's Will Leitch wrote on Thursday. "May, brought in on a one-year deal last December, provided stability and a 4.38 ERA in 109 innings, which eased the burden on a rotation that didn’t have much certainty heading into the year.

"Even with fewer available rotation spots – it would seem Michael McGreevy, Andre Pallante, Kyle Leahy and Quinn Mathews should have a good claim on four of them – the Cardinals may be in the market for a similar free-agent starter this year. It would have to be someone with upside but not coming off a great contract year in 2025, the type of pitcher who might accept a one-year pillow contract. Kris Bubic? Shane Bieber? Heck, May again, after his disappointing stretch run in Milwaukee? It would seem to make some sense."

May made 21 starts with the Cardinals this season and was one of the most sought-after starting pitchers at the trade deadline. His expiring contract and veteran presence made him an attractive option.

Bieber would be a great option for St. Louis to pick up this offseason. Though he's struggled with injuries in the past three years, he's a two-time All-Star and former Cy Young Award winner. If he turns things around next season, he could be a great pitcher for the Cardinals' starting rotation.

Contenders are always looking for starting pitching at the trade deadline, so signing a hurler with upside to flip for prospects or young players could be a great move for the Cardinals, especially as multiple pitching prospects close in on reaching the big leagues.