After trading Rafael Devers, and then signing Roman Anthony to a team-friendly $130 million extension, the Boston Red Sox can spend this winter. And they absolutely should.
Not just by signing Alex Bregman to a long-term contract. But also by signing Kyle Schwarber and bringing the slugger back to Boston.
Signing both players is not going to be cheap. ESPN projected Bregman to sign a five-year, $160 million contract while projecting Schwarber to sign for four years, $128 million. So that would add $288 million to the payroll. But the Red Sox are a big market team and have acted like a small market franchise more often than not in recent seasons.
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It's time for Red Sox to flip their front office script
It’s time to change that. Trading Devers and the entirety of his contract was not about just shedding the salary; it was about reallocating resources. By trading Devers, they saved approximately $254.5 million. So the Red Sox would add slightly more payroll annually while having Bregman, Schwarber, Kyle Harrison and Jordan Hicks.
That would make the Devers trade more palatable for Red Sox fans. And it would signal to the fanbase and clubhouse that the organization is serious about winning, something that team executive Craig Breslow said the organization would do more of after trading Devers.
Besides, the Red Sox know what they are getting in both players. Bregman is loved within the organization and has a great relationship with manager Alex Cora. At 31, there are questions about how a long-term contract could age. But his production in Boston – .273/.360/.462 with an .821 OPS, 18 home runs and 62 RBI – as well as an All-Star Game appearance and his leadership speaks for itself.
The same speaks for Schwarber. In 2021, after he was traded to the Red Sox, Schwarber made a tremendous impression on the organization. Leadership. Production. What he brought on a daily basis. Even manager Alex Cora said during the season that he was “very intrigued” by what Schwarber’s free agency might look like, perhaps tipping his hand that the organization would pursue a reunion.
Adding the right veterans can supplement Red Sox young core
Just imagine Schwarber hitting Schwarbombs at Fenway for the next three-to-five seasons. In 2025, he hit 56 of them. He has hit 94 homers in his last two seasons and 187 in his last four seasons. He’s aging better as his career goes on, and there are no signs he’ll be slowing down any time soon.
The Red Sox have one of the best young cores in baseball, headlined by Anthony. Pairing them with Bregman and Schwarber would 1) take pressure off the young players to perform and 2) infinitely raise the Red Sox’s ceiling in 2026 and beyond. It’s quite possible that adding those two players – and trading for another starter – could vault the Red Sox into the World Series picture.
It’s a critical offseason for Breslow as he tries to win the fanbase over. And there’s no better way for him to do so than by signing two of the biggest names on the market, names the fanbase has already fallen in love with.