Craig Breslow has made some savvy trades during his tenure as chief baseball officer of the Boston Red Sox, but few of them have come at the trade deadline. Boston's late season additions haven't worked out well for it, and Dustin May was no exception.
Fortunately, the St. Louis Cardinals have prevented the Red Sox from forging a potential reunion with the righty. On December 13, May signed a one-year deal with the Cardinals after his first stint in free agency, reported by MLB insider Jeff Passan of ESPN.
May was a promising Los Angeles Dodgers prospect many years ago, but his big league career has been marred and constantly cut short by injuries and inconsistency. He brought the same to Boston, despite a few successful early starts that suggested his luck may have been changing. May let up three runs over his first 15.2 innings with the Sox, but his luck turned soon enough. He finished his tenure with the Red Sox with a 5.40 ERA and a 1.69 WHIP over 28.1 frames.
Boston and St. Louis have swapped a couple of players in the last few months. May will join Blaze Jordan, a first base prospect traded to the Cards for Steven Matz at the trade deadline, and Richard Fitts and Brandon Clarke, the Cardinals' return in the Sonny Gray trade, in the Midwest.
Cardinals sign 2025 Red Sox trade deadline addition Dustin May, (thankfully) preventing potential reunion in Boston
It would be hard to argue that Boston needed to reunite with May, especially after its early rotation additions of Gray and Johan Oviedo from the Pirates. The Red Sox have a deep pool of potential starting pitchers in their system, and May hardly aligns with Breslow's desires to bring in a top-of-the-rotation arm.
However, some may claim that it would've been worth it to give May another shot given his earlier success in the big leagues and the Red Sox's severe overpay for his services at the trade deadline. In 2023, before he underwent Tommy John surgery, he'd posted a 2.63 ERA and a 0.94 WHIP over 48 innings. Those stats are more aligned with the caliber of player Breslow paid for when he traded for May, a sure-fire DFA candidate at the 2025 trade deadline — the Red Sox sent James Tibbs III, one of their returns in the Rafael Devers trade, and fellow outfield prospect Zach Ehrhard to LA for a then-struggling, chronically injured pitcher.
The Red Sox never publicly announced any intention to reunite with May, but Breslow loves a reclamation project pitcher. Boston could've added him to its seemingly endless supply of depth, but May has never pitched more than 132 innings in his career (he'd never even come close to that number before the 2025 season) and it can do better with its boundless financial resources and prospect depth.