The Boston Red Sox over the past several years have been known largely for making some of the worst, most shocking trades in recent memory. The Mookie Betts trade in 2020, sending the American League 2018 MVP to the Los Angeles Dodgers for a three prospects â two of whom are now out of Boston â is perhaps the most prominent.
The Betts trade, made under then-Boston chief baseball officer Chaim Bloom, got some competition in 2025 when Bloom’s successor, Craig Breslow, dealt 215-career-home-run hitter Rafael Devers to the San Francisco Giants, again receiving a package of minor league and borderline players in return.
The Devers trade was certainly the most stunning MLB trade by any team in 2025, but according to top MLB insider and expert Jeff Passan of ESPN.com, the Red Sox also made the single best trade, or transaction of any kind, of the season.
Actually, the trade took place in the offseason, on December 11, 2024. But it would be difficult to find a more consequential move for the Red Sox or possibly any other team.
With the Red Sox appearing primed to qualify for the postseason for the first time since 2021 and only the second since 2018, it is impossible to imagine that they would be in their current position without Breslow’s trade for ace left-hander Garrett Crochet.
‘Plenty of Choices’ For Award
Passan, in his end-of-season “awards” essay for ESPN.com published Tuesday, noted that the Crochet trade had “plenty” of competition for his “Transaction of the Year” honor.
“(Juan) Soto’s contract is an all-timer. Max Fried has been everything the Yankees needed,” Passan wrote. “And there was no shortage of trade options, from the blockbusters (Kyle Tucker to the Cubs, Rafael Devers to the Giants) to the deadline stunners (Mason Miller to the Padres, Carlos Correa back to the Astros).”
But according to the veteran baseball insider, “in terms of sheer impact, though, the Red Sox’s December acquisition of Crochet is unbeatable. And it’s among the most infrequent of trades, too: one in which both parties emerge elated.”
Both Red Sox, White Sox ‘Win’ Trade
The Red Sox, of course, acquired Crochet who has become a top Cy Young candidate and true, top-of-the-rotation ace for the Red Sox. With a 17-5 won-loss record and 2.69 ERA, Crochet ranks second in wins to Fried in MLB, and third in the American League in ERA, behind the Detroit Tigers’ Tarik Skubal (2.23) and Houston Astros Hunter Brown (2.30).
Crochet also leads the Major Leagues in strikeouts with 249, and is third in the AL in WAR at 5.6 behind Skubal (6.5) and Brown (6.2).
But the White Sox, a team that remains in a rebuilding phase, also took a big step in their rebuild adding four top prospects â three of them already on the Chicago MLB roster. The fourth, outfielder Braden Montgomery, was Boston’s first-round draft pick in 2025.
Middle infielder Chase Meidroth, pitcher Wikelman Gonzalez, catcher Kyle Teel â the No. 4 ranked prospect in the Red Sox system at the time of the trade, have all made their big league debuts with the White Sox this season.
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