There's no need to remind you how bad the Dustin May trade was for the Boston Red Sox. A last-minute trade deadline pickup — likely born out of sheer desperation once the team failed to land Joe Ryan or another frontline starter — the right-hander collapsed upon arrival, recording a 5.40 ERA and -0.1 fWAR across just five starts.
The team let him walk in free agency, getting practically nothing in exchange for James Tibbs III and Zach Ehrhard, both of whom have blossomed into top prospects with the Los Angeles Dodgers.
Such is life under the leadership of Craig Breslow. What's more pertinent to today is that May, now a member of the St. Louis Cardinals, is rumored to be on the trade block again according to USA Today's Bob Nightengale.
The Cardinals, in fact, are expected to trade RP JoJo Romero and SP Dustin May at the trade deadline, per @BNightengale pic.twitter.com/ZEtlRlTvzB
— SleeperMLB (@SleeperMLB) June 7, 2026
In case anyone is thinking about trading for him, I'm sure the Red Sox could offer a lengthy slideshow suggesting all the reasons not to.
Red Sox will avoid Dustin May at all costs... but may trade for his Cardinals teammate
Though he is pitching much better than he did after last year's trade deadline, it goes without saying that May isn't coming back to Boston. Both sides had a pretty harrowing experience when they partnered up, and really the only thing the Red Sox don't need more of is middling-at-best starting pitchers.
Instead, they could express interest in JoJo Romero, May's teammate in St. Louis who was also mentioned by Nightengale as a likely trade candidate. The lefty reliever broke out in a big way last year, even earning some closer opportunities once Ryan Helsley was shipped out. Though he hasn't repeated that performance in 2026 — his ERA (3.45 from 2.07) and FIP (3.81 from 3.28) have both risen — he remains an effective set-up man who befuddles left-handed batters to the tune of a .214 batting average.
That's a role Danny Coulombe was supposed to fill this season, but it's safe to say he's fallen out of favor with Chad Tracy. Also consider that Greg Weissert has allowed roughly 100,000 inherited runners to score, Justin Slaten has an ERA above 6.00, and Garrett Whitlock only just returned from the injured list, and it's clear that the Red Sox could use another high-leverage reliever (or two).
Such a trade will only be swung if the team starts winning enough to justify bringing in a rental reliever, but Romero would help solve a glaring issue on the roster. At the very least, trading for him couldn't possibly go worse than trading for May, right?
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