Womp womp.
Craig Breslow came to the Red Sox front office as almost a complete unknown. We knew he was a pitching guy, obviously. We knew that Theo liked him. We knew that he went to an Ivy League school and considered studying medicine and spent most of his playing career as the smartest guy in the room (though that’s not hard to do when you’re frequently in a room with Jonathan Papelbon). But we didn’t know what kind of GM he would be.
Do we know what kind of GM he is now?
Coming into today, you could easily make an argument that he was the type of GM who liked to go big. Two of his first moves were the trades of Alex Verdugo and Chris Sale. He put together a massive prospect package to land a guy who is going to finish in the top-five of the Cy Young voting this year in Garrett Crochet. He traded away the team’s best hitter.
Maybe he hasn’t quite been AJ Preller — baseball’s version of Napolean Bonaparte, casually selling the territory of Louisiana from his bathtub — but Breslow has not been afraid to rock the boat, seeming to be a markedly different strategist than the risk-allergic Chaim Bloom.
But not today. Though there was a flurry of reports about a last-minute effort to pry Joe Ryan away from the Twins, the Red Sox concluded the 2025 trade deadline with two moves that only marginally improve the team, if at all.
Just before the deadline, the Sox acquired starting pitcher (and pending free agent) Dustin May from the Dodgers in exchange for James Tibbs, one of the prospects recently acquired in the Rafael Devers deal. Dustin May has spent his career as a tantalizingly talented pitcher who could never stay healthy. He’s thrown some of the nastiest pitches I’ve ever seen come out of a starter’s hand… he’s also posted a negative bWAR this season and has already thrown by far the most innings of his career as he recovers from an esophageal tear that he suffered while recovering from Tommy John surgery. He has time to turn things around this season, but if good Dustin May ever emerges again, it’ll probably be on whatever team he signs with as a free agent in the offseason. It’s hard to call him an upgrade over Richard Fitts for the rest of 2025.
Steven Matz, while hardly a game-changer, is a useful piece to have in your bullpen. And the Red Sox essentially got him for free. Blaze Jordan was not going to be protected from the Rule 5 Draft this winter, and guys like Blaze Jordan — defensively limited right-handed power hitters who put up slightly better than league average stats in AAA — are really, really easy to find. I’m pretty sure the coffee shop down the street from me gives you a free Blaze Jordan if you get 10 punches on their loyalty card.
Matz, meanwhile, will immediately be thrust into a high-leverage role, particularly against lefties. And while it seems like the Red Sox bullpen is a little unbalanced vis-a-vis left-handers, Brennan Bernardino’s been worked so hard that the tendons in his elbow are threatening to go on strike alongside the Fenway concessions workers, so it’s a good idea to get him some help. Matz also a guy who has spent the majority of his career as a starter, and made two five-inning starts back in April, so he could be plugged into the depth chart there, though obviously he hasn’t been stretched out.
As to the big question: did the Red Sox do “enough”? That’s impossible to answer, in no small part because, thanks to the bloated playoff format, it’s hard to know what “enough” means. Any team that can get to, oh say, 86 wins can get to the postseason. And any team that can get to the postseason can win the World Series. If that’s the goal, then the Red Sox started the day with “enough,” if only just.
But the problem with the Red Sox is that they’ve been deliberately shooting for “just enough” for five straight years. They’ve been tip-toeing into both the trade and free agent market instead of diving in, operating under the misguided belief that payroll and roster flexibility automatically lead to roster quality.
This year should have been different. Alex Bregman and Aroldis Chapman could be on new teams in 2026. Ceddanne Rafaela could regress from his All-Star form. Garrett Crochet could be on an operating table at Mass General (that’s just the reality of pitching today — you’re never guaranteed another start, let alone another Cy Young caliber season). And yet Breslow couldn’t swing a deal to put the team over the top.
The Red Sox can still make the postseason and they can still win the World Series. That’s just how baseball works. But with a chance to meaningfully improve the roster, the Red Sox yet again failed to meet the moment, preferring to kick the can down the road once more.
What kind of GM is Craig Breslow? Today, he was John Henry’s kind.