After their brief return to the postseason in 2025, the Boston Red Sox are expected to be one of the most active teams this offseason. They have money to spend in free agency after the Rafael Devers trade and they have a deep farm system of prospects to flex on the trade market.
It's hard to estimate Boston's exact offseason plan because its spending in the last half decade hasn't exactly reflected a desire to compete for championships. Chief baseball officer Craig Breslow has helped the team take steps in the right direction in 2025 by signing Alex Bregman and trading for Garrett Crochet, but it's been quite some time since the Red Sox signed someone to a megadeal from the free agent market, which is what Bregman, Pete Alonso or Kyle Schwarber would demand.