Cardinals Sign Dustin May, Quietly Closing the Door on a Red Sox Reunion That Never Needed to Happen
Craig Breslow has made some sharp moves since stepping into the role of chief baseball officer in Boston, but the trade deadline hasn’t exactly been his sweet spot. One of the most glaring examples?
Dustin May. The right-hander came to the Red Sox with some promise, but his short stint in Boston was more of a cautionary tale than a comeback story.
Now, the St. Louis Cardinals have taken that decision off the table.
On December 13, May signed a one-year deal with the Cardinals, marking his first foray into free agency. And while the move may not make major headlines nationally, it quietly spares the Red Sox from a potential reunion that never really made much sense.
May’s Boston Run: A Flash, Then a Fizzle
Once a top prospect in the Dodgers’ system, May’s career has been a rollercoaster of high hopes and hard landings. Injuries and inconsistency have been the defining themes, and his time in Boston followed that same script.
When he first arrived, there were flickers of what once made him so highly regarded. In his first 15.2 innings with the Red Sox, he allowed just three earned runs.
But the wheels came off not long after. He wrapped up his time in Boston with a 5.40 ERA and a 1.69 WHIP over 28.1 innings - numbers that reflect a pitcher who couldn’t find his footing.
For a team looking to stabilize its rotation, that’s not the kind of performance you can bank on.
A Trade Deadline Miss
May wasn’t just a gamble - he was an expensive one. At the 2025 trade deadline, the Red Sox sent outfield prospects James Tibbs III and Zach Ehrhard to the Dodgers in exchange for a pitcher who, at the time, was struggling to stay healthy and effective. That deal looked questionable from the start, and it aged quickly.
To make matters worse, Tibbs had been part of the return in the blockbuster Rafael Devers trade - a high-profile move that already carried its own weight of scrutiny. Giving up a key piece of that return for a short-term flyer on May only added to the frustration.
Yes, May had flashed elite stuff in the past - a 2.63 ERA and 0.94 WHIP over 48 innings in 2023 before undergoing Tommy John surgery - but that version of him never showed up in a Red Sox uniform.
Cardinals Step In, Red Sox Move On
With May now heading to St. Louis, he joins a growing list of familiar names making their way to the Midwest. He’ll be alongside Blaze Jordan, the first base prospect Boston dealt for Steven Matz at the deadline, as well as Richard Fitts and Brandon Clarke, who came over in the Cardinals’ Sonny Gray trade.
For the Red Sox, this feels like a bullet dodged. The team has already made meaningful additions to its rotation this offseason, bringing in Sonny Gray and Johan Oviedo. And with a deep pool of arms in the system - both at the major league level and in the pipeline - there’s no pressing need to roll the dice on a reclamation project like May.
Even if Breslow has shown a soft spot for pitchers with something to prove, May doesn’t quite fit the mold of what Boston needs right now. He’s never thrown more than 132 innings in a season, and even that number is a stretch. For a club with the resources and prospect capital Boston has, they can aim higher - and they should.
No Harm, No Foul - Just Moving Forward
To be clear, there’s no indication the Red Sox were actively pursuing May this offseason. But given the way his name had floated around after his brief Boston stint, it wasn’t out of the realm of possibility that a reunion could’ve been on the table.
Now, that’s no longer a concern. The Cardinals get their shot at unlocking May’s potential, and the Red Sox can continue building a rotation that’s more reliable, more durable, and more aligned with their long-term goals.
Sometimes, the best moves are the ones you don’t make.