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Dustin May puts Cardinals fans in an uncomfortable spot with Brewers' World Series title on the line

Wasn't expecting that when the trade went down!
ByJosh Jacobs
Oct 24, 2026; Milwaukee, Wisconsin, USA;  Milwaukee Brewers pitcher Dustin May (21) throws a pitch against the Tampa Bay Rays during the fifth inning in game two of the 2026 World Series at American Family Field.  Mandatory Credit: Benny Sieu-Imagn Images
Oct 24, 2026; Milwaukee, Wisconsin, USA; Milwaukee Brewers pitcher Dustin May (21) throws a pitch against the Tampa Bay Rays during the fifth inning in game two of the 2026 World Series at American Family Field. Mandatory Credit: Benny Sieu-Imagn Images | IMAGN IMAGES via Reuters Connect

The Milwaukee Brewers are one win away from their first World Series title in franchise history, and former St. Louis Cardinals starting pitcher Dustin May has been tabbed as their Game 4 starter in this potentially historic day.

I don't know about you - but that's an odd thing to wrap my head around!

May, who signed with the Cardinals this offseason on a one-year deal to rebuild his value, did just that during his 21 starts with the Cardinals, posting a 4.38 ERA in 109 innings pitched. May had a few blow-up starts mixed into his campaign with St. Louis, but most nights when he took the mound, he was a dynamic starter who could put the Cardinals in a position to win. This eventually led to a strong trade market for May, and the Brewers gave up two top outfield prospects, Josiah Ragsdale and Alexander Frias, to acquire both May and JoJo Romero for their World Series push.

Romero has been a dynamic arm out of the Brewers' bullpen this postseason, and May has split time as a starter and reliever as well.

The return still seems to be a home run for the Cardinals, but it's hard not to at least feel off about May potentially going down in history as the man who started the most important game in Brewers history.

Cardinals got young talent back, but Dustin May is helping the Brewers win the World Series

The Cardinals stood nothing to gain from holding onto May beyond this year's trade deadline, so dealing him made all of the sense in the world. And, frankly, getting the best possible return matters far more than who the team is that acquires May.

Still, with that being said, it does feel a bit odd that May is being tabbed to start this historic game for the Brewers tonight from a Cardinals' perspective.

On one hand, it should be the ultimate compliment to the Cardinals' process this offseason. They identified May as a good fit for what they wanted to do, presented him with a plan to get the most out of him, got him to sign on the dotted line, and executed that plan. It resulted in two different outfield prospects that different prospect evaluators see as top 100 prospects, which is about as good of a return as you could possibly hope for.

And now May is starting a pivotal game for the juggernaut Brewers, showing that the Cardinals did just smoke and mirrors their way to this trade deadline haul, but they actually were able to send out a starter that a World Series-caliber team would want to acquire.

So, that's the main storyline here, and the one the Cardinals' front office obviously values most. But from an emotional standpoint, it still stings a little.

If May was starting the potential World Series clinching game for the Rays, Guardians, or even the Dodgers, it wouldn't hurt as bad. But seeing him help a division rival, one that is going to be extremely difficult to catch up to in the coming years, is a tough pill to swallow.

Now, if Ragsdale and Frias pan out, that's going to feel a whole lot better lately.

So no, I'm not at all complaining about how this trade went down. The Cardinals nailed it and would do it 100 times over again. But if May does end up adding "World Series clinching starting pitcher for the Brewers" to his resume, that'll be an odd one!

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