Everything about the Boston Red Sox trading for Dustin May last season reeked of failure. To begin with, Walker Buehler's failure in Boston forced the Red Sox into a last-minute deadline hunt for an MLB-proven starter. In its search, Boston failed to trade for Joe Ryan. Then, lacking all leverage (and desperate), they settled on an overpay for May ... who failed.
May ultimately succumbed to an elbow injury and wasn't able to finish the season for the Red Sox, but it was actually for the best. In 28 1/3 innings of work, the right-hander tallied a 5.40 ERA and 1.69 WHIP in a Red Sox uniform. Meanwhile, to get May, the Red Sox had given up James Tibbs III (one of their prizes from the Rafael Devers deal), who dominated in Double-A for the Dodgers (.900 OPS). Not ideal.
May was back in the headlines this week, this time as a signal of how inflated-beyond-belief the price for starting pitchers has gotten. Per ESPN's Jeff Passan, May signed with the St. Louis Cardinals on a deal that will pay him $12.5 million in 2026, with a $20 million mutual option for 2027.
Dustin May's deal with the St. Louis Cardinals is official, sources tell ESPN. He will make $12.5 million this year, and the mutual option for the 2027 season is for $20 million.
— Jeff Passan (@JeffPassan) December 17, 2025
Dustin May just got paid an exorbitant amount of money for his mediocre services, and Red Sox fans are in disbelief
Is this Chaim Bloom's idea of a hilarious joke aimed at his former club? It would be costly comedy if so, because handing May a potential $32.5 million bag of money over the next two seasons only stands to have people laughing at the Cardinals.
Meanwhile, Red Sox fans are in utter shock. May is earning 56 percent more salary than Freddy Peralta next season. Make it make sense.
What would be even more ridiculous is if May finds any sort of success in St. Louis, mirroring how Buehler suddenly remembered how to pitch again once he joined the Philadelphia Phillies in 2025, or how Quinn Priester became the star he was always meant to be as soon as he left the Red Sox in a trade to the Milwaukee Brewers.
It's not an impossible outcome. May's always showed flashes of quality, and he's not old, having just turned 28 in September. The Dodgers felt good enough about May's talent to take him in the third round of the 2016 MLB Draft. He had a really promising 2020 MLB season (though shortened), starting for LA on Opening Day and ending up No. 5 in NL Rookie of the Year voting.
Will May finally settle in, stay healthy, and produce for St. Louis? Bloom is paying him like he expects that to happen. At this point, Red Sox fans would be strangely unsurprised if it did.