Red Sox Whiff On Full Display As 28-Year-Old Lands With Cardinals

The Boston Red Sox missed on this one...

Aug 18, 2025; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Dustin May (85) delivers a pitch during the second inning against the Baltimore Orioles at Fenway Park. Mandatory Credit: Paul Rutherford-Imagn Images | Paul Rutherford-Imagn Images

The Boston Red Sox were looking for some starting pitching ahead of the 2025 Major League Baseball trade deadline, but unfortunately, things didn't work out.

Boston acquired Dustin May from the Los Angeles Dodgers for outfielder James Tibbs III (Boston's then-No. 5 prospect) and outfielder Zach Ehrhard (the then-No. 27 prospect). That was a pretty big haul at the time for Los Angeles. Now, the deal looks even worse for Boston. May made just six appearances for Boston -- including five starts. He had a 5.40 ERA over that span and didn't make an appearance in the playoffs for Boston.

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He entered free agency after the season and now reportedly has found a new home with ESPN's Jeff Passan reporting that he is in agreement on a deal in free agency with the St. Louis Cardinals.

Not the best move for Boston

"Right-hander Dustin May and the St. Louis Cardinals are in agreement on a free agent contract, pending physical, sources tell ESPN," Passan wrote on X on Saturday.

Fortunately, Boston is loaded in the outfield and has a ton of pitching depth now because this move would've looked even worse now if not. The Red Sox acquired Tibbs in the Rafael Devers trade and didn't hold onto him for long.

May's time in Boston was short and in the grand scheme of things won't have a big impact. Boston's outfield is seemingly set for years to come and the rotation should be good in 2026. But it's clear that the summer trade was a whiff. There was no way to know it would turn out how it did, but two prospects -- including the team's then-No. 5 prospect -- for just six appearances and then an exit in free agency isn't exactly what you want.

A reunion never seemed likely, but now that he has reportedly agreed to a deal with St. Louis, now is a time to reflect. The Red Sox had a lot of hits in 2025 -- like Garrett Crochet, Aroldis Chapman, Alex Bregman, and Carlos Narváez -- but also some high-profile misses, as well.

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