The Boston Red Sox's 2025 trade deadline is widely considered a failure. Instead, Craig Breslow, the team's chief baseball officer, decided to invest in lower-tier additions to help push the team over the hump and into the postseason.

Boston is five games behind first place in the AL East and were surging right before the All-Star break following a trade that sent its slugger Rafael Devers to San Francisco. Instead of going all-in at the deadline, the team made minor moves, including bringing in often-injured starting pitcher, Dustin May, from the Dodgers.