The Boston Red Sox are fresh off what looks like their first successful trade deadline in years, though the outcome truly remains to be seen. New additions Curtis Mead and Adley Rutschman are on the injured list, but Jake Rogers, Eli White and Erik Miller all address some of Boston's biggest needs before its playoff push.
Many former Red Sox — including one Craig Breslow trade deadline addition and one subtraction — were dealt to contenders to help them get ahead. Hopefully, they have better luck with their new teams than they did in Boston (unless the Red Sox end up playing them in the postseason).
3 former Red Sox traded at 2026 deadline feature pieces of regrettable Craig Breslow deals
Dustin May
Red Sox fans might remember the Dustin May trade forever, and not in a good way. Less than an hour before the 2025 trade deadline, a few incorrect reports made Sox fans think the team had landed Minnesota Twins All-Star Joe Ryan for its playoff push. Instead, Boston ended up with May, who was a near-certain DFA candidate from the Los Angeles Dodgers. May posted a 5.40 ERA over 28.1 innings with the Sox before he fell injured.
May signed with the St. Louis Cardinals over the offseason and he clocked a 4.38 ERA and 106 strikeouts over 109 innings with them. The Cards traded him to the division-rival Milwaukee Brewers as their consolation prize for losing out in the Tarik Skubal sweepstakes.
Nathaniel Lowe
Nathaniel Lowe came to the 2025 Red Sox after the trade deadline, following his placement on waivers by the Washington Nationals. His tenure in Boston began on a high note after he notched three extra-base hits — a home run and two doubles — in his first three games. He batted .280/.370/.420 over 34 games through the end of September.
Lowe signed a minor league contract with the Cincinnati Reds just before spring training 2026 and he batted .266/.341/.480 with 17 doubles and 12 home runs over 83 games with them. Cincinnati traded him to the Cleveland Guardians, where he is tied with rookie phenom Chase DeLauter and Kyle Manzardo for second place on the team home run leaderboard.
Ryan Zeferjahn
Like Dustin May, Ryan Zeferjahn was part of another unsuccessful Breslow deadline trade. The Red Sox selected Zeferjahn, then a starting pitcher, in the third round of the 2019 MLB Draft. He and three other prospects were traded to the Los Angeles Angels in exchange for reliever Luis Garcia.
Zeferjahn made his MLB debut with the Angels shortly after the trade and he posted a 2.12 ERA and 0.76 WHIP over 17 innings. Two years later, Anaheim traded the flamethrower to the Chicago Cubs as a much-needed bullpen reinforcement, as the Cubs have 14 pitchers on the injured list after deadline day.
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