The Cardinals signed Dustin May last December knowing they could likely flip him to a contender for prospects at the MLB Trade Deadline. The Cards are excited about getting promising outfield prospects Alexander Frias and Josiah Ragsdale from the rival Brewers for May and JoJo Romero.
Over 21 starts with the Cardinals, Dustin May compiled a 5-7 record and a 4.38 ERA and that production cost the club roughly $8.5 million. However, the 6-foot-6 right-hander’s time with the Cardinals will go down as a success and his salary could be worth every penny paid if two returning prospects pan out.
First, the 28-year-old May served as a valuable mentor for young hurlers Michael McGreevy, Matthew Liberatore, Andre Pallante and Kyle Leahy by imparting some of the wisdom he has picked up over an eight-year MLB career filled with some impressive highs and plenty of forgettable lows.
The St. Louis stint for May, who was traded along with veteran left-handed reliever JoJo Romero to the rival Milwaukee Brewers on Monday, will also go down as a success because of the splashy, promise-filled return that he commanded for a Cardinals club still in full-on rebuild mode.
President of baseball operations Chaim Bloom, who has worked feverishly for months to restock the Cards Minor League system with young talent, was able to extract 18-year-old outfielder Alexander Frias and 22-year-old speedster Josiah Ragsdale out of the Brewers in exchange for renting May and Romero for the rest of the season and the playoffs.
Additionally, the Cardinals were able to acquire pitching prospects Daniel Eagen, Sando Santana and a player to be named later from the Diamondbacks in exchange for outfielder Lars Nootbaar. The 6-foot-4 Eagen was the No. 5-ranked prospect in the Dbacks system after striking out 153 hitters in 2025 and 109 in 87 1/3 innings in 2026.
With the Cardinals likely still in building mode in 2027, could the sign-and-flip model be one that the Cardinals use to their advantage again at the MLB Trade Deadline in 2027? Could mid-tier free-agent pitchers such as Robbie Ray, Zac Gallen, Chris Bassitt, Jack Flaherty or Kevin Gausman sign with the Cardinals with the understanding that they could be flipped to a contender for prospects before next August?
Minor League talent evaluators were shocked that the Brewers – owners of MLB’s most talent-rich Minor League system – would surrender two players seemingly with superstar potential to the in-division rival Cardinals for two pitchers who will be free agents at the end of the season. Frias, already 6-foot-2 at 18 years old, was rated as one of the top prospects in baseball in the Arizona Complex League by Baseball America. Meanwhile, the 22-year-old Ragsdale homered in his first at bat with Double-A Springfield on Wednesday night, allowing him to join the 20-doubles (21), 20-homers (20) and 20-stolen bases (31) club while slashing .318/.442/.589/1.031 in 87 Minor League games in 2026.
“We were happy with what we were able to do,” Bloom said on Cardinals TV on Tuesday night. “It’s a wild time of year, but there are always opportunities. Any position you are in, there are opportunity to move yourself forward, and we were happy with the things we were able to complete.”
Was Brewers’ move a panic response to what the Dodgers did in getting Tarik Skubal? Do the Brewers think that May’s heat -- when paired with Jacob Misiorowski and Kyle Harrison – can help them win a seven-game series? Can Romero’s history of effectiveness against lefties like Bryce Harper, Kyle Schwarber, Shohei Ohtani and Freddie Freeman push them over the top and help them get to a World Series for the first time since 1982? Also, there’s this concern: Will Milwaukee someday regret helping the hated Cardinals and have to face Frias and Ragsdale 13 times a season?
“We liked what we were able to get back in the deal with the Brewers,” Bloom said. “We got two outfielders who are at different spots in their journeys, but we think they both have the upside to impact the game at the highest level.
“Frias is just getting going and in the first part of his stateside journey and he’s producing like crazy and he has the type of tools to match (that of a star player). He has the type of tools and upside that is really hard to find in trades like these, especially with the current production he has already shown. And the upside is huge on this guy – power, speed, offense and defense … it’s all there.
“And when you talk about power and speed and a well-rounded game, you are talking about things that Josiah Ragsdale brings. He’s further along in his journey as a college player who is already at Double-A and is having a tremendous year. He’s been more of a speed-and-line drive guy who is starting to come into some pop and he’s starting to drive the baseball. So, we’re really excited to add him to a really talented outfield at Double-A.”
Cards always had plans of flipping May
From the time that the Cardinals signed May last December to what amounted to be a one-year, $12.5 million free-agent deal, the front office knew that there might be a situation where the club could flip the veteran for prospects at the deadline. May, 28, also understood that very real scenario and he looked at St. Louis as a place to go and rehabilitate his career.
One factor in signing with the Cardinals, May admitted, was the organization’s history of keeping starting pitchers healthy. Incredibly, the Cardinals have not had a starting pitcher go on the Injured List with an arm injury over the past two seasons. Also, only one reliever, Max Rajcic, has suffered an arm injury since September of 2024 when Romero was placed on the IL as a precautionary measure after the Cards had already been eliminated from the playoffs.
Manager Oliver Marmol and pitching coach Dusty May closely monitor the workloads of pitchers in the early months of the season when elbow, shower and forearm injuries are the most prevalent. Also, they have been proactive in sprinkling in a sixth starter to the rotation during times when the pitching staff is being taxed over long stretches of games.
That tactic has worked wonders this season. The Cardinals went into Wednesday’s 3-1 win over the Yankees with a 3.99 ERA from their starting pitchers in 2026 – the first time the starting staff’s ERA was lower than 4.00 since 2022 (3.97). One of the staff’s best reclamation projects – Andre Pallante – limited the Yankees to three hits and one earned run over 5 1/3 innings on Wednesday for his career-best 12th victory.
May has seen much of his promise as a frontline pitcher marred by arm injuries that have caused him to miss parts of four MLB seasons. Even last season, when the Dodgers finally gave up hope that May could ever thrive in their system and traded him to the Red Sox, May battled shoulder soreness and arm fatigue late in the season.
In St. Louis, May made the second most starts (21) of his career, pitched the second most innings (109) and recorded the second most strikeouts (106). It’s probably no coincidence that the Brewers were the team most interested in acquiring him considering how he pitched against Milwaukee while leading the St. Louis staff.
May took a no-hitter into the seventh inning in Milwaukee before exiting after surrendering just two hits and one earned run and striking out nine on May 27. Then, on July 6 in St. Louis, May was dominant again in a designed abbreviated start because he had previously been dealing with back pain: 4 2/3 scoreless innings, four hits, seven strikeouts and no walks.
