The Boston Red Sox’s 2025 trade deadline is widely considered a failure. They did not add a top-of-the-line starting pitcher or fill their void at first base.
Instead, Craig Breslow, the team’s chief baseball officer, decided to invest in lower-tier additions to help push the team over the hump and into the postseason. On Wednesday, the team acquired left-handed reliever Steven Matz. On deadline day, Breslow struck a similar deal.
According to ESPN’s Jeff Passan, the Red Sox are acquiring right-handed pitcher Dustin May from the Los Angeles Dodgers in exchange for outfield prospects James Tibbs III (#5) and Zach Ehrhard (#27).
May was the odd man out of the Dodgers’ rotation with former Cy Young winner Blake Snell set to return in the coming weeks. This season, May has appeared in 19 games, including 18 starts, and totaled a 6-7 record with a 4.85 ERA and 97 strikeouts across 104 innings. May was reportedly unwilling to return to a bullpen role, which ultimately led to his departure. He will likely reunite with former teammate Walker Buehler in the backend of Boston’s rotation.
While adding May is an adequate move, the package going to Los Angeles is perplexing. Tibbs III was not only the Red Sox’s number five prospect but was the headlining player in the Rafael Devers trade.
Although the team has surged up the AL Wild Card standings and is in striking distance of the division, trading away the prospect chosen in the package for Devers two months later is head-scratching. It is unknown whether the organization’s feelings toward Tibbs III soured shortly after his acquisition, but to deal him for a rental arm makes the Devers trade even more confusing.
Time will tell whether the move pays off for Boston, but in the immediate aftermath, it feels like a massive overpay on their behalf.
