The St. Louis Cardinals could be preparing for an intriguing offseason reunion as former starting pitcher Dustin May emerges as a potential candidate to return to St. Louis for the 2027 MLB season. With the franchise continuing its rebuilding process under president of baseball operations Chaim Bloom, the possibility of bringing back a familiar veteran has become an interesting talking point ahead of another important winter.
According to an October 26 report by Curt Bishop of Heavy Sports, May has been identified as a possible addition to the Cardinals’ rotation after spending part of the 2026 season with St. Louis before being traded to the Milwaukee Brewers. The suggestion follows an assessment by MLB.com’s Will Leitch, who included May among five veteran starting pitchers who could make sense for the Cardinals next season.
Although no agreement has been reached and there is no confirmed indication that formal negotiations have begun, the potential reunion presents an opportunity for St. Louis to strengthen its pitching staff without making a massive long-term financial commitment.
Cardinals Face Important Pitching Decisions After Promising 2026 Campaign
The Cardinals entered the 2026 season with considerable uncertainty surrounding their immediate future. With Bloom overseeing a long-term organizational restructuring, the franchise focused on developing younger players, improving its farm system and creating a more sustainable foundation for future success.
Despite finishing with a disappointing 77-85 record, St. Louis remained competitive for much of the campaign and stayed in the postseason conversation until the final stages of the regular season. The team demonstrated encouraging signs of progress, but its overall performance also exposed several weaknesses that management must address before 2027.
One of the biggest concerns involves the pitching staff. While the starting rotation showed periods of stability, the bullpen struggled with consistency, and the organization could benefit from another dependable veteran capable of handling a significant workload.
The Cardinals have several promising young pitchers developing within the organization, but relying exclusively on inexperienced arms could create additional challenges during a rebuilding season. Adding an established starter would provide valuable experience while allowing younger pitchers to develop without being forced into demanding roles prematurely.
That situation makes May an intriguing candidate. His previous experience with St. Louis means the organization already has some understanding of his strengths, personality and ability to work with its pitching staff.
Dustin May’s Previous Cardinals Success Strengthens Reunion Possibility
May’s first stint with the Cardinals was relatively brief, but it provided evidence that he could contribute to the team’s rotation.
The right-handed pitcher joined St. Louis ahead of the 2026 campaign after spending much of his earlier major league career with the Los Angeles Dodgers. Once considered one of baseball’s more exciting young pitching talents, May had endured several injury-related setbacks that prevented him from consistently fulfilling his potential.
However, his move to St. Louis gave him an opportunity to rebuild his value while establishing himself as a dependable major league starter.
During his time with the Cardinals, May produced a 5-7 record and a 4.38 ERA across 21 starts. He also recorded 106 strikeouts against 35 walks over 109 innings, demonstrating that he could still generate swings and misses while providing useful innings for a developing rotation.
His performance was not dominant, but it represented meaningful progress for a pitcher whose career had been repeatedly interrupted by physical setbacks.
Beyond the statistics, May reportedly embraced his role as an experienced presence among the Cardinals’ younger pitchers. That leadership element could become especially valuable if St. Louis decides to bring him back.
The Cardinals ultimately traded May to Milwaukee before the deadline, using his improved value to acquire additional young talent. The transaction also involved reliever JoJo Romero and brought prospects Alexander Frias and Josiah Ragsdale into the organization.
That deal demonstrated how a short-term veteran signing could support the Cardinals’ rebuilding strategy in more than one way: improving the major league roster while potentially creating valuable trade opportunities.
Milwaukee Struggles Could Open Door for Unexpected Return
Although May helped strengthen Milwaukee’s pitching depth following the trade, his performance with the Brewers was less convincing than his earlier work in St. Louis.
He finished the 2026 regular season with a combined 7-9 record and a 4.70 ERA across 31 starts. His performance after joining Milwaukee was particularly disappointing, as he recorded a 5.65 ERA in 10 regular-season starts.
Those struggles raised questions about his ability to consistently perform as a reliable middle-of-the-rotation starter for a championship contender.
Nevertheless, his durability represented a significant positive development. After battling injuries for several seasons, May managed to remain healthy throughout the 2026 campaign, an achievement that could help restore interest in his services.
His postseason experience with Milwaukee also provided additional exposure to high-pressure baseball, even though his results remained inconsistent.
Leitch’s assessment emphasized that May still possesses an effective fastball and has not yet reached his 30th birthday. That combination of remaining upside and recent durability makes him an interesting option for clubs searching for affordable starting pitching.
For St. Louis, the possibility of acquiring a familiar pitcher whose market value may have declined after a difficult second half could represent a calculated opportunity rather than a major financial gamble.
Contract Situation Could Determine Whether Cardinals Pursue Reunion
One of the most important factors surrounding a possible reunion involves May’s contract.
The Cardinals originally signed him to a one-year, $12.5 million agreement that included a $20 million mutual option for 2027. However, that option is widely expected to be declined, potentially allowing May to enter free agency once the offseason officially begins.
If May becomes available, St. Louis could explore another short-term agreement similar to the arrangement that brought him to the organization before the 2026 season.
A one-year contract with an option for 2028 could provide flexibility for both sides. The Cardinals would gain a veteran starter without committing to a lengthy agreement, while May would receive another opportunity to strengthen his market value.
A multiyear arrangement containing opt-out provisions is another possibility discussed in the report, although such terms remain hypothetical.
The financial structure would be especially important because the Cardinals are not currently operating as a franchise expected to pursue expensive veteran additions at the expense of their long-term rebuilding strategy.
Instead, Bloom could prioritize contracts that balance affordability, immediate usefulness and future flexibility.
If May performs well, the Cardinals could retain him as an important rotation contributor. If the team struggles in the standings, he could potentially become a trade candidate again, allowing St. Louis to acquire additional prospects.
This approach would closely resemble the strategy that helped the organization benefit from May’s first stint with the franchise.
Cardinals Must Balance Veteran Experience With Long-Term Development
While the possibility of re-signing May is appealing, the Cardinals must also consider the broader direction of their pitching development.
The organization has invested considerable effort in strengthening its farm system, with several young pitchers expected to compete for opportunities over the coming seasons.
Prospects such as Liam Doyle, Jurrangelo Cijntje and Tanner Franklin represent part of the franchise’s longer-term pitching plans. Their development could eventually reduce the need for outside additions, but the Cardinals still face the challenge of maintaining a competitive rotation while those players progress.
Bringing back May would not necessarily prevent younger pitchers from receiving opportunities. Instead, he could provide an experienced option capable of absorbing innings and reducing pressure on prospects who may not yet be prepared for a full major league workload.
However, there are risks. May’s injury history cannot be ignored, and his struggles after joining Milwaukee suggest that his performance could remain unpredictable.
The Cardinals would need to determine whether his success in St. Louis was the beginning of a sustained improvement or simply a productive stretch within an otherwise inconsistent season.
The decision could ultimately depend on his asking price, medical evaluations and the availability of other starting pitchers.
Will St. Louis Actually Bring Dustin May Back in 2027?
For now, a reunion between Dustin May and the Cardinals remains a proposal rather than a confirmed transaction.
There is no reported agreement, no announced contract offer and no guarantee that St. Louis will prioritize May once the free-agent market develops.
Still, the circumstances surrounding his potential availability make the idea worth considering.
The Cardinals need pitching experience, May previously enjoyed a productive stretch with the organization, and his disappointing results in Milwaukee could make another short-term agreement financially realistic.
Most importantly, a reunion would align with the Cardinals’ rebuilding philosophy if the organization believes May can provide immediate value without compromising its future plans.
For May, returning to St. Louis could offer the stability and familiar environment needed to build on his healthiest season in years. For the Cardinals, it could represent another opportunity to acquire a veteran capable of contributing on the field while potentially becoming a valuable asset later.
The biggest question is whether Bloom believes May can repeat his earlier success in St. Louis. If the Cardinals decide that the benefits outweigh the risks, the former starter could find himself wearing the same uniform again when the 2027 season begins.
With the offseason approaching, May’s contract situation will be one worth watching as St. Louis evaluates how aggressively it wants to strengthen its starting rotation.
The original October 26 report presents Dustin May as a suggested reunion candidate, not a confirmed Cardinals signing or active negotiation.
Leave a Reply