Boston Red Sox fans went into the trade deadline dreaming of Joe Ryan and Jhoan Durán. They ended up with Dustin May and Steven Matz. In what is becoming a frustrating pattern, Craig Breslow eschewed risk in favor of marginal improvements to one of the hottest teams in MLB.
Maybe it all works out — the Red Sox sure feel like a World Series threat right now — but for a team with so much talent, both on the MLB roster and in the farm system, a more seismic addition was possible. Breslow's unwillingness to roll the dice and go all-in could be viewed as his fatal flaw.
Boston's rotation needed the most work. May, a former top Los Angeles Dodgers prospect, arrived with a 4.85 ERA 1.35 WHIP in 19 games (18 starts) this season. He has 97 strikeouts in 104.0 innings. While the talent is substantial, May has struggled to command his pitches and string together consistent outs in his age-27 season. He's on an expiring contract.
His Red Sox debut did not go well. He allowed six hits, a walk and three earned runs in 3.2 innings in a 7-3 loss to the Kansas City Royals.
Dustin May has arrived at Fenway. pic.twitter.com/ncDL6uL0bB
— Red Sox (@RedSox) August 6, 2025
For more news and rumors, check out MLB Insider Robert Murray’s work on The Baseball Insiders podcast, subscribe to The Moonshot, our weekly MLB newsletter, and join the Discord to get the inside scoop during the MLB season.
Dustin May's Red Sox debut exposes feeble rotation
Dustin May being the "big" trade deadline addition for Boston was always going to age poorly. While taking a swing on a clearly talented 27-year-old is totally worthwhile, the Red Sox didn't just add him for free. Boston sacrificed its No. 5 prospect, 22-year-old outfielder James Tibbs III. That is a not-insignificant piece to give up for a struggling pitcher in his walk year.
There are positive signs as May embarks on his Red Sox career, including a change in approach that relies more heavily on a slick cutter. But until May can command his pitches and get more swings-and-misses, it will be tough sledding. He likes to let his defense carry the load with a high sinkerball volume, but May leaves too many pitches floating over the middle of the plate for batters to feast on.
He projects more as an innings-eating reliever than a viable starter in October. Boston will be relying on Lucas Gilito and Walker Buehler to an uncomfortable extent in the playoffs as a result.
James Tibbs III makes strong early impression with Dodgers' Double-A affiliate
As fate would have it, James Tibbs hit his first home run as a member of the Dodgers farm system on Wednesday, the same day as May's Red Sox debut. In fact, Tibbs drilled two home runs, bringing him up to 15 on the season in 91 games between High-A and Double-A.
Top #Dodgers OF prospect James Tibbs III has homered twice so far today for Double-A Tulsa
— Bruce Kuntz (@Bnicklaus7) August 7, 2025
He was drafted 13th overall last year by the Giants before getting traded to Boston in the Rafael Devers package and recently to L.A. in the Dustin May deal pic.twitter.com/lsRVogZJtl
Tibbs, a 2024 first-round pick who arrived in Boston as part of the Rafael Devers trade, has been up and down throughout the season, but he has big-league power and a clear path to the majors within the next couple years. If the Dodgers can turn May's expiring contract into a future starting outfielder, that will qualify as a huge win. It's clear May would not have re-signed in L.A. this winter.