The Milwaukee Brewers are one win from the first World Series title in franchise history, and their Game 4 starter comes with a familiar name for St. Louis: Dustin May.
For Cardinals fans, that creates a strange little knot. May spent this season in St.
Louis after signing a one-year deal designed to rebuild his value, and he did exactly that. In 21 starts for the Cardinals, he logged a 4.38 ERA across 109 innings.
Some outings got away from him, sure, but more often than not he gave the club a chance to win and revived his market in the process.
That market led to a deal the Cardinals clearly wanted to make. Milwaukee sent two top outfield prospects, Josiah Ragsdale and Alexander Frias, to land May and JoJo Romero for its championship chase. Romero has been a real weapon out of the Brewers’ bullpen this postseason, while May has worked both as a starter and a reliever.
From the Cardinals’ side, the return looks strong. They didn’t stand to gain anything by keeping May past the trade deadline, and getting the best possible haul mattered more than which contender ended up with him. By that measure, the front office did its job.
Still, it’s hard to ignore the optics. May is now in position to start the most important game in Brewers history, and that’s a weird place for Cardinals fans to land.
If he were doing this for the Rays, Guardians, or even the Dodgers, it would sting less. But helping a division rival potentially finish off a title run carries a different kind of discomfort.
The bigger picture, though, still points back to St. Louis making the right call.
The Cardinals identified a fit, got May to buy into their plan, and turned that into two prospects who are viewed by different evaluators as top 100 talents. If Ragsdale and Frias develop, this trade will look even better.
So yes, the Cardinals handled the move the way they should have. But if May winds up as the pitcher who starts the Brewers’ clincher, that’s going to be one odd line on a resume.
In Other News...
Cardinals Suddenly Face One Offseason Problem They Can't Ignore
The Cardinals are heading into another winter with the attention shifting away from deadlines and toward the kind of roster repair work that can shape the next couple of seasons. After missing the postseason for the fourth straight year, St. Louis appears poised to lean more heavily on free agency than trades as it tries to patch obvious holes at third base, in the starting rotation and in the bullpen.
That makes the pitching side especially hard to ignore, because the clubs hopes of being more competitive in 2027 will depend on how much it can raise the floor of the staff. Internal options will get a look, but the front office is also expected to explore outside help, with names such as Dustin May and Shane Bieber in the mix as the Cardinals search for arms that can stabilize both the rotation and relief corps. [Read more 🡒]
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Stanek gave the Cardinals plenty of innings in 2026, working in 70 games and finishing with a 4.02 ERA after settling in following a rough opening stretch. Even so, the cost of bringing him back at the option number could make the club hesitate, especially if the belief is that he might return on a lower deal once the market resets. For a bullpen that will always be judged on both effectiveness and efficiency, this is the kind of move that can leave fans wondering whether the safe choice and the smart one are the same thing. [Read more 🡒]
Cardinals Head Into A Pivotal Offseason With Familiar Names At Risk
With the 2026 season in the books, the Cardinals are already shifting into a winter defined by hard choices and familiar names. Nolan Gorman, Ryan Stanek, Yadier Herrera and Juan Yepez are all among the players the front office may have to weigh against roster fit and future needs as St. Louis starts mapping out its 2027 plan.
The biggest pressure points are easy to spot: third base, catcher and designated hitter all loom as spots the Cardinals may want to address. That leaves this offseason with a familiar St. Louis feel, where the decisions are less about chasing new faces than deciding which current pieces still belong in the conversation and which ones could be moved on from. [Read more 🡒]
