The Boston Red Sox have managed to stay firmly in the playoff conversation-even after dealing away Rafael Devers earlier this year in a move that stunned much of the baseball world. That speaks volumes about the roster construction and performance they’ve gotten elsewhere, particularly from one high-profile addition: Alex Bregman.
Bregman came to Boston on a three-year, $120 million deal this past offseason, and he hasn’t just filled in the gap-he’s established himself as the centerpiece. Now fresh off an All-Star campaign, there’s plenty of buzz that Bregman will explore the opt-out clause in his contract once the season ends. And given the year he’s having, the market could be ready to hand him a massive payday-potentially in the neighborhood of $200 million, according to league chatter.
From the Red Sox perspective, that’s where things get interesting. They have the option to retain Bregman, and after moving Devers’ contract off the books, they’ve created space to spend. The question is how they’ll allocate it-and whether it’s enough to keep Bregman in Boston.
One path forward that’s gaining traction: moving Masataka Yoshida.
It’s not a knock on Yoshida, who has quietly been more productive than he gets credit for. But it’s becoming clear that Boston doesn’t view him as a long-term fit in the field, and his contract-$18.6 million annually through 2027-is significant. With roster flexibility tightening, particularly at the DH spot, trading Yoshida could be the pivot point that allows the Sox to prioritize keeping Bregman long-term.
Yoshida was brought over with the expectation that his power from Japan (where he routinely posted 20+ homer seasons) would translate. So far in MLB, it hasn’t quite clicked the same way-he’s tallying just 27 home runs across more than 250 games. Still, his approach, contact skills, and ability to get on base offer value, just perhaps not in the exact way Boston envisioned when they signed him.
Moving Yoshida would open up the designated hitter role, further easing some positional logjams and giving the Sox more lineup fluidity. And from a financial standpoint, that $18.6 million annually represents the kind of flexibility that could be crucial in extending or re-signing Bregman.
Bottom line: Boston made a bold decision in dealing Devers, but they’ve stayed in the fight thanks in large part to Bregman’s performance. If they want that success to extend into future seasons, their next move-possibly with Yoshida-could determine whether Bregman remains the cornerstone of the next contending Red Sox team.
