The Boston Red Sox certainly don't look like trade deadline buyers at 12 games below .500 and last-place status in the American League East. Still, the thought of another trade deadline with Craig Breslow at the helm of the organization sends shivers down fans' spines.
Breslow has only experienced two trade deadlines as Boston's chief baseball officer and neither has gone well. He made his first successful trade deadline move last season by acquiring Steven Matz (2.08 ERA over 21.2 innings with Boston) from the St. Louis Cardinals in exchange for infield prospect Blaze Jordan. But the deal was overshadowed by possibly the second-worst trade of the season (besides the Rafael Devers trade Breslow made a month and a half before).
Red Sox fans were shocked to learn that Breslow traded for Los Angeles Dodgers pitcher Dustin May — they minutes before been led to believe that they'd be getting ace Joe Ryan from the Minnesota Twins, and May hardly had desirable numbers at the time (4.85 ERA over 104 frames with the Dodgers). LA's return is really what blew Sox fans away: Breslow gave up top prospects James Tibbs III and Zach Ehrhard for the struggling May.
Even worse, Breslow proposed that return himself, according to new reporting from Tim Healey of The Boston Globe (subscription required). Healey reports that a source said the Dodgers “couldn’t agree to that fast enough.”
New report sheds more light on just how bad Craig Breslow's Red Sox-Dustin May trade was
Not only was Tibbs the No. 5 prospect in the Red Sox organization at the time of the trade, he arrived in Boston as part of the Rafael Devers deal, which could've made him a cornerstone piece in the future. The Red Sox's outfield is still packed and there's no room for Tibbs had they kept him, but they should've been able to get much more for him than a four-plus ERA pitcher.
May would've been an unsatisfactory deadline addition no matter what the Sox gave up for him. He'd already pitched a career-high 104 innings at the time of the trade and his injury proneness caught up with him soon after his arrival. He landed on the injured list with elbow neuritis early in September and never returned to action. May was likely also days from being designated for assignment by the Dodgers, who had Blake Snell coming back from the IL shortly after the deadline.
The Red Sox gave the Dodgers, the best team in baseball and twice-consecutive World Series champions, a treasure chest of a return for a player they were about to let go for nothing, without even negotiating. May wasn't worth one of the Red Sox's top prospects, let alone two, but Breslow just handed them over because he got desperate.
Despite assertions that Breslow's job in Boston's front office is safe, new reports that show the depth of his screw-ups continue coming out. No matter what the Red Sox say, it doesn't seem like they can justify keeping Breslow around for the 2027 season, nor should they.
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