The Boston Red Sox made some risky moves to return to the postseason for the first time since 2021. Boston traded for and extended Garrett Crochet, and signed Alex Bregman to a $120 million deal — two huge moves that helped it get closer to its mission of contending for a World Series.
Chief baseball officer Craig Breslow's trade deadline moves did not have the same effect. Breslow traded for Steven Matz from the St. Louis Cardinals and converted him to a full-time reliever, which worked out for the Sox. Matz posted a 2.08 ERA and a 0.88 WHIP with six holds and a save over 21.2 innings with Boston. The Dustin May trade, however, did not pan out.
Breslow traded for May after whiffing on his attempt to convince the Minnesota Twins to trade their ace, Joe Ryan. Breslow then had to pivot with around 30 minutes until the 6 p.m. trade deadline, and he landed May from the Los Angeles Dodgers.
May posted a 5.40 ERA with 26 strikeouts and 13 walks over 28.1 innings with the Red Sox. He fell injured in early September with elbow neuritis, and couldn't help Boston in the final month of the season or in the playoffs — Lucas Giolito also sustained an elbow injury shortly after, leaving the Sox's pitching staff decimated for the Wild Card series. But May's rough performance and injury aren't the worst aspects of Breslow's deal with the Dodgers.
The Dustin May trade robbed the Red Sox of two easy outfield trade candidates for the upcoming offseason
The Red Sox sent their then-No. 5 prospect James Tibbs III and then-No. 27 Zach Ehrhard to the Dodgers for May, who's never posted a full season of work in his career. LA was also trying to figure out what to do with May in their own pitching staff because Blake Snell returned from injury right around the time of the trade deadline and their 40-man roster was full, but Breslow solved their rotation logjam for them by accepting a DFA-candidate for two top-30 prospects.
It stings even more that Tibbs came to Boston as part of the Rafael Devers trade with the Giants. Tibbs, a highly-touted outfielder, could've played for the Red Sox at some point, or he could've been part of a bigger offseason trade for elite pitching, such as one for Ryan or Sandy Alcántara. One thing's for sure: May's 4.85 ERA over 104 innings with the Dodgers and half a season of team control wasn't worth Tibbs, let alone Tibbs and Ehrhard.
Because of this frantic, frivolous deal, the Red Sox are down two potential trade candidates they could've used this offseason. Boston's farm system and pool of young talent are still stacked, but holding onto Tibbs could've allowed them to keep another member of their outfield later on, like Jarren Duran, Wilyer Abreu or Jhostynxon Garcia.