Craig Breslow has dabbled in extremes during his short tenure as chief baseball officer of the Boston Red Sox, particularly on the trade market. While he swapped four prospects for Garrett Crochet in possibly the best move of hs career, he also traded Rafael Devers for peanuts over easily preventable drama.
Trade deadlines, in particular, have not been Breslow's forte, and 2025 was rough. Steven Matz was a great addition, but Red Sox Nation can't say the same about Dustin May.
The Red Sox sent top outfield prospects James Tibbs III (then-No. 5) and Zach Ehrhard (then-No. 27) to the Los Angeles Dodgers for May, who was mere days from being designated for assignment to make room for Blake Snell's return off the injured list. To make matters even worse, Boston fans were briefly under the impression that Breslow landed Joe Ryan from the Minnesota Twins (it still hurts to think about).
In spring training, Tibbs is balling out and fans around MLB have started rubbing salt in the wound. The outfielder on March 22 crushed his fourth home run in 21 Cactus League games, and he's posted a 1.107 OPS on the spring.
Baseball fans around MLB letting Red Sox have it for Dustin May trade as Dodgers prospect James Tibbs III keeps improving
Tibbs for May is probably the worst trade in MLB last year and it was so overshadowed by the Devers trade that we haven't given the Sox enough shit for it https://t.co/geCE1rVQRd
— Jacob (@AndThatsBB) March 23, 2026
Red Sox fans knew immediately that the Dodgers fleeced Boston in the May trade, but Tibbs' continued improvements only make the deal look worse. Not only was May well past his career-high in innings pitched at the time of the deal, meaning fatigue could set in at any time during the Sox's playoff push, he also landed on the IL with elbow neuritis after just six appearances.
How many trades this decade had a worse process then James Tibbs for half a year of Dustin May https://t.co/K6m2L3K0UG
— Griff (@Jram2TBJ) March 23, 2026
The Red Sox made two trades that aged like milk last season. They traded Devers, their only true power hitter in the lineup, during a career offensive year and their lineup severely lacked pop afterwards. Tibbs was part of the return in the Devers trade — it's looking like he was the best part — but he didn't last long with the Sox. Then, Alex Bregman signed with the Chicago Cubs in January, removing the only reason Boston traded Devers in the first place from its lineup.
The Red Sox, somehow, managed to make themselves worse on the trade market in 2025. Hopefully, fans of other teams who are tired of seeing Boston give LA incredible players for free let Breslow have it for the May trade all over again (subscription required). Swinging for a massive player at the trade deadline, such as Ryan, can be a team's downfall when it has no backup plan.