After a turbulent start to the 2025 season during which the club jettisoned their superstar Rafael Devers in a blockbuster trade, the Boston Red Sox were able to stabilize their season. They found themselves eight games above .500 and holding a Wild Card spot when the July 31st deadline closed in.
Fans anticipated a solid deadline out of chief baseball officer Craig Breslow after the Sox played such good baseball in the lead-up to July 31. Despite their play, there were still a few glaring additions the team needed to make, with a second starter and first baseman at the top of the list.
However, the deadline came and went, and like those of the past few seasons, Red Sox fans were left hugely disappointed. Breslow only landed left-handed reliever Steven Matz for first base prospect, Blaze Jordan, in a trade with the St. Louis Cardinals. While this trade drew the ire of some, with fans claiming Jordan was too good a prospect to give up, Breslow’s next and final trade of the deadline sent Red Sox Nation into uproar. It led many to believe that, like the Mookie trade, shipping Devers off to the Giants was purely a salary dump.
In the aftermath of the Devers trade, Breslow remained steadfast in his assertions that Boston would be a buyer come July 31st, with controllable starting pitching being at the top of the club’s list. And while Breslow eventually did acquire a starter, it was a deal that completely contradicted his stated intentions.
The acquisition of Dustin May rounds out the Red Sox's poor deadline
In the closing hour of the deadline, Breslow made his final move of the day, landing starter Dustin May in a deal with the Los Angeles Dodgers. To no surprise, this was a hugely underwhelming acquisition for the Red Sox. For one, May’s career has been plagued with injury concerns, as on top of missing all of 2024 due to UCL surgery, before 2025, May had never thrown more than 56 innings in a season. In addition to his many injury concerns, May is also in the last year of his contract, making him set to be a free agent at the end of the season.
Unfortunately for the Red Sox, things get even worse when considering the return the Dodgers got. In exchange for two months of May and his 4.85 ERA and 84 ERA+, Breslow gave up two top 30 prospects, No. 5 James Tibbs III, and No. 27 Zach Ehrhard.
The inclusion of Tibbs makes this trade hard to swallow, as in addition to starting prospect Kyle Harrison, Tibbs was seen as a centerpiece in Boston’s return for Devers. Thus, given his tremendous value, it is borderline malpractice that Breslow was only able to fetch a rental of an injury-riddled pitcher with an ERA close to five.
Many fans hoped that Breslow would use the assets from the Devers trade to put together a package for Minnesota Twins ace Joe Ryan. In reality, it seems money truly was the main reason for shipping out their homegrown superstar.