The 2025 trade deadline ended up being a dud for the Boston Red Sox. Chief baseball officer Craig Breslow only made two trades. The first was acquiring left-handed reliever Steven Matz from St. Louis. Matz was solid for Boston, posting a 2.08 ERA across 21 outings. The other trade was the real screw-up.
In a last-second panic move, Breslow sent James Tibbs III and Zach Ehrhard to the Los Angeles Dodgers for starting pitcher Dustin May. Breslow had been eyeing Twins All-Star Joe Ryan and had apparently been in deep talks that never amounted to much. The only other acceptable option the Sox had in mind was Arizona's Merrill Kelly, but he was dealt to Texas. Wanting to make a move, Breslow called the Dodgers and brought in May.
May was already having a rough year in LA (he had a 4.85 ERA in 104 innings) and was being moved to the bullpen. Things only got worse in Boston. The righty made just five starts, six appearances, posting a 5.40 ERA. The oft-injured pitcher was once again bitten by the injury bug in Boston, too, making the trade an utter disaster.
The Cardinals might be able to do what the Dodgers did to the Red Sox with Dustin May
Over the offseason, May eventually ended up signing with the Cardinals. A rough first two outings in St. Louis are pulling his numbers down, but he has seemed to find his stride for the Redbirds. In his last seven starts, the 28-year-old has a 3.54 ERA in 40.2 innings. He has struck out 31 batters and has a WHIP of 1.30 in that stretch.
Trade deadline updates, per @BNightengale:
— Underdog MLB (@UnderdogMLB) May 17, 2026
• Rival executives say Antonio Senzatela will be "one of the hottest commodities" at deadline
• Matt Shaw could be trade candidate as Cubs search for a front-line starter
• Teams are "keeping a close eye on" Riley O’Brien, JoJo… pic.twitter.com/3o3qJVkBqN
May only signed a one-year deal in the offseason, meaning the Cardinals could trade him at the deadline if they are out of the playoff race, which they might do because they are just starting a rebuild. It sounds like he could be a hot commodity, too. According to Bob Nightengale, May is one of three pitchers teams are "keeping a close eye on."
Mays's renaissance is a little embarrassing for the Red Sox's "great" pitch lab. For a team whose current identity is getting the best out of pitchers, May was a flop. Now St. Louis has May throwing primary fastballs and cutters cut the usage of his sweeper and sinker way down. The Cards have also gotten his pitch velocities back up to when he was at his most dominant in 2023.
If the Cardinals can flip May for a solid prospect haul, it'll be just another reminder of how bad Breslow screwed up the 2025 trade deadline. It was obvious to everyone that acquiring May was a panic decision and that they were fleeced by the Dodgers. The Sox are supposed to be able to help figure a pitcher out, and another team being able to do that and not them is just embarrassing.
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