The Boston Red Sox have had rough luck with most of their trades since last season. Most of the players they've dealt since sending Rafael Devers to San Francisco have had jealousy-inducing levels of success with their new teams.
Even Dustin May has fared well. The Red Sox traded for May from the Los Angeles Dodgers at the 2025 trade deadline, seemingly days before he was set to be designated for assignment. He posted a 5.40 ERA and 1.65 WHIP over 28.1 innings with Boston before a bout with elbow neuritis ended his season early.
May's performance has turned around with the St. Louis Cardinals, and he may even be asserting himself as a trade deadline candidate again. The righty has posted a 4.57 ERA with 51 strikeouts and 17 walks through 61 innings. His May 27 outing was his best yet — he pitched seven hitless innings against the division rival Milwaukee Brewers. He eventually gave up two hits and a run, but his seven-frame appearance was his longest of the season and his nine strikeouts are the most he's thrown all year.
May is the least of Boston's worries when it comes to former pitchers dominating with their new teams. Kyle Harrison's turnaround with the Brewers has been brutal for Red Sox fans to see.
Former Red Sox pitchers Dustin May, Kyle Harrison and David Sandlin continue to embarrass Craig Breslow
It’s really insane how much better every player is when they are in any other organization than Boston https://t.co/DhPVG5DJiy
— Alex (@Alexzachary305) May 27, 2026
Harrison arrived to Brewers camp in the spring with a new pitch in his arsenal and he reinvented himself in the Midwest. Harrison logged a 4.04 ERA over 35.2 innings in the big leagues with the Red Sox and San Francisco Giants last season, and he's been putting that number to shame this year. Harrison has posted a 1.57 ERA, 1.03 WHIP, 61 strikeouts and 14 walks over 51.2 innings. His ERA is the lowest any Brewers starter has ever had in their first 10 games, besting a record previously held by CC Sabathia.
Even rookies have put the Red Sox to shame with their new clubs. Boston salary-dumped Devers trade return Jordan Hicks to the Chicago White Sox in February, and top pitching prospect David Sandlin was the sweetener in the deal.
Sandlin made his MLB debut for the White Sox on May 27 and stunned Chicago fans. He allowed a leadoff homer to get off to a rocky start, but quickly set himself right. Sandlin retired 18 consecutive batters to set a White Sox record and fanned four batters over six innings. He didn't allow another hit, he didn't walk anyone and he got through six innings with just 61 pitches.
Craig Breslow has made some very successful trades since taking over as chief baseball officer in Boston — the Garrett Crochet and Willson Contreras deals are both aging well. But the sheer number of people he's traded who then perform exceedingly well with their new teams should raise some eyebrows, either from a talent assessment or player development standpoint.
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