Red Sox Plan Aggressive Offseason to Retain Bregman, Build Championship Team

After an 89-73 season that ended with a Wild Card loss to the Yankees, Red Sox chief baseball officer Craig Breslow said Boston is closer to its championship goal but still short of where it wants to be and will pursue external acquisitions with ownership willing to provide resources (Sporting News; SI). The front office expects a busy offseason—major roster moves are likeliest after the World Series and around the Winter Meetings—while also making difficult internal decisions to focus on winning (SI). The biggest immediate storyline is Alex Bregman’s opt-out: he’ll test free agency, and although there is mutual interest in a return, he reportedly wants longer-term security than Boston currently guarantees (SI). New York appears unlikely to be a major suitor because Ryan McMahon’s contract limits their payroll flexibility, but multiple contenders (including the Dodgers, Tigers, Cubs, Mariners and other clubs) are expected to pursue Bregman aggressively (SI; Newsweek). Bregman battled a quad injury in 2025 but still produced offensively and provided clubhouse leadership, meaning his eventual destination will be pivotal to whether the Red Sox can take the next step from 89 wins to bona fide contention (Newsweek; Sporting News).