Red Sox Waste Opportunity With Abhorrent Trade Deadline

The Red Sox only acquired Steven Matz and Dustin May, much to the disappointment of every Boston fan out there.
Jul 28, 2025; Minneapolis, Minnesota, USA; Boston Red Sox relief pitcher Jorge Alcala (71) flips his glove as he leaves the game against the Minnesota Twins in the sixth inning at Target Field. Mandatory Credit: Bruce Kluckhohn-Imagn Images
Jul 28, 2025; Minneapolis, Minnesota, USA; Boston Red Sox relief pitcher Jorge Alcala (71) flips his glove as he leaves the game against the Minnesota Twins in the sixth inning at Target Field. Mandatory Credit: Bruce Kluckhohn-Imagn Images | Bruce Kluckhohn-Imagn Images

The Boston Red Sox had many holes to fill at this year's deadline, which was in their bullpen, starting rotation, and at first base. Many names were used as potential trade candidates for the Red Sox, guys like Zac Gallen, Joe Ryan, Sandy Alcantara, Edwin Cabrera, Mitch Keller, Ryan O'Hearn, Yandy Diaz, Griffin Jax, and Jeffrey Springs.

These were just SOME of the names being thrown out on social media, and they all had legs to them. Craig Breslow showed this past offseason that he wasn't messing around, going after Garrett Crochet, Alex Bregman, and Walker Buehler. He showed he wasn't afraid to trade prospects, especially with how he got Crochet from the White Sox, trading Kyle Teel (#3), Wikelman Gonzalez (#7), Chase Meidroth (#19), and Braden Montgomery (who the Red Sox drafted 12th overall in 2024).

They were four of the top 30 prospects in the Red Sox farm system at the time, but it showed that Breslow was different than Chaim Bloom: he wanted to compete and win a World Series, and wasn't afraid to part with prospects to get it done. Much like Theo Epstein before him.

However, this year was a repeat of last year's deadline, where the Red Sox acquired James Paxton, Danny Jansen, Quinn Priester, Luis Garcia, and Lucas Sims. All of which were absolutely terrible with the Sox in the second half of the season.

This year, Breslow made all these promises on "bolstering the lineup" and that he "believed in this team." Everyone said he had better be able to back up those big statements, and what does he do? He goes for low-key buys.

First, he acquired Steven Matz from the St. Louis Cardinals, who was having an okay stretch this season in the bullpen. Then, in the final minutes, with no other deal happening in the meantime, Breslow struck again. When everyone expected Craig to acquire Joe Ryan from the selling Twins (who made 9 total trades and dismantled almost their entire roster), the Red Sox got Dustin May from the Los Angeles Dodgers instead.

May, for one, is actually a fairly good pitcher. He's got amazing stuff and will work well with Andrew Bailey, but here's the problem: he can't go deep into games. Like Tanner Houck before him, he's got amazing stuff but doesn't have the stamina to go far. In fact, in his last start against the Red Sox, he was impressive. He struck out five in his appearance and held the Red Sox down to two runs as the Dodgers were up 3-2. However, he crumbled in the 6th inning and gave up a two-run HR to Alex Bregman to take the loss.

As for first base? They got nobody. Nobody. That is the disappointing part, as well as not acquiring Joe Ryan at the deadline. It shows their overbelief in the team, and just like Dustin May, they'll fall apart down the stretch. The phrase that matches this deadline? "Close, but were never close enough".

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