After the Boston Red Sox's failed push for Joe Ryan under a half an hour before the MLB trade deadline, chief baseball officer Craig Breslow had to do something. He called up the Los Angeles Dodgers and traded for starting pitcher Dustin May to deepen his rotation.
The trade has gone poorly for Boston — about as poorly as all the rest of its trades with LA tend to do. Not only was May having a rough year in the Dodgers' rotation, he'd already surpassed his career high in innings and Breslow sent James Tibbs III, one of the returns from the Rafael Devers trade, to LA for, essentially, a DFA candidate. Now that May is on the injured list in Boston, the move looks even worse.
May posted a 5.40 ERA with 26 strikeouts and 13 walks over 28.1 innings since he was traded to the Red Sox. Boston placed him on the IL, retroactive to September 6, with elbow neuritis, and he hasn't been cleared to throw, which makes it hard to believe it'll be seeing him on the mound again this year. Meanwhile, Tibbs raked in the Dodgers' minor league system.
Tibbs didn't get off to the best start with Double-A Tulsa, but he found his way in September. The outfielder slashed .269/.407/.493 with a .900 OPS over 36 games with the Drillers, and he batted .357/.460/.786 in 11 games in September. He clocked eight extra-base hits, including four home runs, in his last eight games.
Former Red Sox prospect James Tibbs III raked with the Dodgers while Dustin May struggled in Boston
3 straight games with a homer for James Tibbs III 🚀
— MLB Pipeline (@MLBPipeline) September 10, 2025
The @Dodgers' No. 8 prospect has an .848 OPS with 27 RBIs in 31 games for the Double-A @TulsaDrillers: pic.twitter.com/Tk8i7dptdK
May's trip to the IL to likely end his season is unfortunate, but the trade was a disaster even before his injury. Not only is Tibbs a severe overpay for a struggling pitcher who's never pitched more than 56 innings in his career before this year, but Boston should've had bigger plans for him as part of the Devers trade. The Red Sox could've used him as part of a trade for elite pitching this offseason or as another part of their outfield youth movement. Instead, the Dodgers fleeced the Red Sox again because Breslow got desperate with the clock ticking.
The Red Sox's outfield logjam is deep, and they may have traded for Tibbs with the plan to eventually use him as a trade piece. But effectively getting May in the Devers trade is a worst-case scenario outcome for the front office, which looks even worse because Jordan Hicks hasn't worked out, either.