Even at the time, the Boston Red Sox’s Dustin May trade reeked of desperation. Rumors of the team aggressively pursuing Joe Ryan fizzled out as the trade deadline drew closer, and at the last minute, Craig Breslow executed a trade with the Los Angeles Dodgers for the starting pitcher.

In exchange for the 27-year-old right-hander, Breslow surrendered outfield prospects James Tibbs III and Zach Ehrhard. Tibbs, of course, was the top prospect acquired in the Rafael Devers deal with the San Francisco Giants.

Predictably, the deal didn’t work out for Boston. Tibbs posted a .900 OPS with the Dodgers’ Double-A affiliate while Ehrhard hit .282/.391/.466 at the same level. Meanwhile, May clocked a 5.40 ERA, 5.39 FIP, 19.5% strikeout rate, and 1.69 WHIP in 28 1/3 innings with the Red Sox.

His tenure with the team was cut short by an elbow injury, which was a sad reminder of May’s injury-prone profile. His 132 1/3 frames between the Dodgers and Sox this year were, by far, the most innings he’s thrown in a season in his career (it was the first time he’d crossed even 60 innings).

Sometimes, you make a bad move and you just have to cut your losses, right? May is an impending free agent, and there’s no further harm in letting him walk in free agency. But… what if they choose to re-sign him?

Dustin May shockingly fits Red Sox’s free agent profile

If you’ve paid attention to the way the Red Sox have done business in free agency in recent years, you’ve probably noticed that they like to target high-upside arms with injury concerns. Lucas Giolito, Liam Hendriks, and Patrick Sandoval were all signed to two-year deals with the understanding that they would miss most if not all of the first year of their respective contracts to rehab from injury.

There’s no information out there that suggests May will miss all of 2026. Though considering he’d thrown all of 191 2/3 innings from 2019-23 before missing the entire 2024 season, it’s a safe bet to assume he’ll miss at least a chunk of time on his next contract.

Now, May was clearly a shell of his younger self in 2025, as his fastball velocity was down more than three miles per hour from its peak, and Baseball Savant graded him out as below average in nearly every notable pitching metric. But that was also true before the Red Sox traded for him; clearly, if the front office was willing to trade Tibbs just six weeks after acquiring him, they saw something in May’s profile to justify it.

Plus, May did find some success in Boston. His health didn’t allow him to make enough appearances to really apply any fundamental changes to his arsenal or mechanics after arriving to his new team, but he did deliver back-to-back quality starts in August against the Houston Astros and Baltimore Orioles. In those two starts, he allowed just two runs in 12 innings while striking out 13.

Given his injury history, May is going to have to settle for a prove-it deal. His talent is undeniable, even if his results have never matched. Andrew Bailey’s pitching factory has already produced a number of surprising contributors — perhaps May, on a very low-risk contract, could become the next success story in Boston.