If you blinked at the 2025 MLB trade deadline, you might’ve missed it. Dustin May, the flamethrowing righty with the signature red hair, briefly called Fenway Park home. It was one of those "high risk, high reward" moves that GMs love to talk about in press conferences but usually end up regretting over a cold beer in November.
Honestly, the Red Sox Dustin May era was more of a cameo than a starring role.
The trade happened on July 31, 2025. Craig Breslow, trying to patch together a rotation that was leaking oil, sent two legitimate prospects—James Tibbs III and Zach Ehrhard—to the Dodgers. In return, Boston got a rental. They got the "hope" of 100-mph sinkers. But what they actually got was a guy who was clearly still fighting his own body after years of medical procedures that would make a surgeon wince.
The Trade That Didn’t Age Well
Let’s be real: the Dodgers kind of fleeced Boston here.
It sounds harsh, but look at the numbers. At the time of the deal, May was struggling in LA with a 4.85 ERA. Breslow and the Sox brass bet on the "stuff." They thought they could unlock that pre-injury dominance. Instead, May’s velocity was down—his sinker was sitting around 94.5 mph, nearly two ticks lower than his 2023 peak.
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He made six appearances for Boston. Only five starts.
The results? Not great. A 5.40 ERA over those 28.1 innings. There was one bright spot—a six-inning scoreless gem against the Astros where he fanned eight—but that felt more like a cruel tease than a turning point. By early September, the wheels fell off. Right elbow neuritis landed him on the shelf, and just like that, the experiment was over.
Why the Red Sox Let Him Walk
You’ve probably seen the news by now: Dustin May is a St. Louis Cardinal.
In December 2025, he signed a one-year, $12.5 million deal to head to the National League. For Red Sox fans, seeing that number might sting, but you have to look at the context. Boston is in a weird spot. They’re trying to build something sustainable, and sinking $12 million into a "maybe" isn't always the move when you've already lost prospects like Tibbs in the process.
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The medical file on May is basically a novel at this point:
- Tommy John surgery (2021)
- Flexor tendon repair (2023)
- Esophagus tear (2024—yeah, that actually happened while he was eating dinner)
- Elbow neuritis (2025)
Basically, the Red Sox saw enough in those six games to decide they didn't want to be the ones paying for the next chapter of the rehab saga. May claimed in November 2025 that he was "fully back to normal" and had put his weight back up to 220 pounds, but "normal" for May hasn't existed since 2020.
The Prospect Cost: The Real Sting
The most frustrating part for Sox fans isn't even May’s performance; it’s who they gave up. James Tibbs III, a top-10 prospect who Boston had just acquired in the (equally controversial) Rafael Devers trade to the Giants, is now lighting it up in the Dodgers' system.
It’s the classic "Dodgers win again" narrative. They traded a struggling, injury-prone pitcher for a high-ceiling outfielder who fits their timeline perfectly. While the Red Sox were desperate for an arm to push them into the 2025 postseason, they ended up with a 1-4 record from May and a missed playoff berth.
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What’s Next for Boston’s Rotation?
With May out of the picture, the Red Sox are looking at a 2026 rotation that feels... incomplete.
You’ve got Garrett Crochet at the top, which is great. Brayan Bello is still there, and Lucas Giolito is expected to provide some veteran stability. But there's a huge hole where a reliable #3 or #4 should be. There’s talk about kids like Connelly Early making the jump from Triple-A Worcester, or maybe another dip into the trade market.
The Red Sox Dustin May saga is a cautionary tale about the "stuff" trap.
In modern baseball, teams are obsessed with spin rates and velocity. But as the Sox learned the hard way, you can’t pitch if you aren't on the mound. May has the talent to win a Cy Young if he ever stays healthy for 30 starts. But for Boston, he’ll just be a "what if" that cost them a couple of future starters.
If you’re tracking the Red Sox roster for 2026, keep an eye on these specific pivots:
- Monitor the health of Tanner Houck: He’s coming off a flexor strain and is the key to the middle of the rotation.
- Watch the "Devers Trade" fallout: The fan base is still reeling from losing Raffy; if the pieces they got back (like Jordan Hicks) don't perform, the pressure on the front office will be immense.
- Look for "low-stakes" signings: The team recently grabbed Seth Martinez on a minor league deal—expect more of these "depth" moves rather than the $100 million splashes fans are craving.
The Dustin May era in Boston was short, expensive, and ultimately a letdown. But that's the risk of the deadline. Sometimes you swing for the fences and you just end up with a sore elbow and a $12 million bill.