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.

The Red Sox traded three prospects in total to acquire starter Dustin May and reliever Steven Matz before Thursday’s 6 p.m. trade deadline.

The Red Sox occupy the second wild-card spot and sit just five games back of the Blue Jays in the AL East, putting them in a solid spot to reach the playoffs for the first time since 2021. Coming into the deadline, the Red Sox wanted to address two areas — first base and starting pitching.