The Boston Red Sox’s trade for Dustin May last season was a gamble that didn’t pay off - and now, it’s resurfacing in headlines for all the wrong reasons.
Let’s rewind. The Red Sox, scrambling at the deadline after Walker Buehler’s stint in Boston went sideways, found themselves in urgent need of a reliable arm.
Joe Ryan was reportedly a target, but that deal never materialized. With time ticking and leverage gone, Boston pivoted to Dustin May - a talented but injury-prone right-hander - and paid a steep price to get him.
That price? James Tibbs III, a promising outfield prospect acquired in the Rafael Devers trade.
Tibbs went on to rake in Double-A for the Dodgers, posting a .900 OPS and looking every bit like the kind of bat you’d want to hang onto. Meanwhile, May struggled to stay on the mound.
In just 28 1/3 innings for Boston, he posted a 5.40 ERA and a 1.69 WHIP. Then came the elbow injury, cutting his season short.
Fast forward to this week, and May is once again making news - this time for the contract he just signed with the St. Louis Cardinals. According to reports, the deal will pay him $12.5 million in 2026, with a mutual option for 2027 that could push the total value to $32.5 million over two seasons.
That’s a significant payday for a pitcher who hasn’t thrown a full, healthy season since 2020. Red Sox fans, understandably, are scratching their heads.
Not only did May underperform in Boston, but now he’s earning more than Freddy Peralta next season - by a margin of over 50 percent. That’s a tough pill to swallow for a fanbase still processing how much talent has walked out the door in recent years.
And yet, here’s the twist: it wouldn’t be shocking if May figures it out in St. Louis.
We’ve seen this before. Walker Buehler, the same pitcher who couldn’t find his rhythm in Boston, rediscovered his form with the Phillies in 2025.
Quinn Priester, another arm the Sox moved on from, blossomed into a frontline starter after landing with the Brewers. Sometimes, a change of scenery - and a healthy elbow - can make all the difference.
May, still just 28, has always had the raw stuff. The Dodgers saw enough in him to take him in the third round back in 2016.
He flashed real potential during the shortened 2020 season, starting on Opening Day for L.A. and finishing fifth in NL Rookie of the Year voting. His sinker has life, his velocity is there, and when he’s right, his stuff plays.
The big question is whether he can stay healthy and consistent. The Cardinals are betting big that he can. And while that contract might look inflated now, it’s a reflection of today’s market for starting pitching - where even upside alone can command eight figures.
As for the Red Sox, this is another reminder of how high the stakes are when you’re dealing from a position of desperation. They needed a starter in a hurry, and they paid a premium for one who couldn’t deliver. Now, they’re watching from afar as May gets a fresh start and a big check somewhere else.
If he turns things around in St. Louis, it won’t just be the Cardinals celebrating. It’ll be another case of “what could’ve been” for Boston - a club still trying to turn the page on a series of high-risk moves that haven’t quite panned out.