The Boston Red Sox have been arguably the most aggressive team in baseball when it has come to the trade block this winter.
Boston has pulled off three high-profile swaps to bring Sonny Gray, Willson Contreras, and Johan Oviedo to town. That’s not all, though. Boston acquired Jake Bennett from the Washington Nationals and cut ties with a few players from the organization, like Vaughn Grissom, in various deals.
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Boston still has work to do, and re-signing Alex Bregman would be a near-perfect move. Bregman remains the top available free agent fit for Boston and one thing that should give fans hope is that MassLive.com’s Chris Cotillo called a reunion “Plan A.”
What’s next?
“Speaking to people with the Red Sox, it’s clear that Plan A, at this point in the winter, is locking down a reunion with Alex Bregman, though the sides have yet to line up on a deal to this point,” Cotillo wrote. “With teams like the Cubs, Diamondbacks and Blue Jays in the mix for Bregman, it’s no guarantee that he does return, though as MassLive reported Sunday night, the Sox remain hopeful — while not necessarily optimistic or pessimistic — that common ground can eventually be found with Bregman. Re-signing Bregman and installing him at third base is perhaps the cleanest way to finish off the heavy lifting of the offseason.”
The Red Sox still have work to do if they want to be atop the American League standings in 2026. That is especially the case for the infield. The trade block has been good for Boston, but The Athletic’s Ken Rosenthal weighed in and noted that free agency should be the team’s next route to add on “Foul Territory.”
“You can’t keep trading from your system, and Brendan Donovan would cost more in prospects than Contreras or Gray did,” Rosenthal said. “So I expect — and I’ve written — that their next move should be a big free-agent hitter. Whether it’s Bregman or Bichette, even someone else.”
Rosenthal isn’t wrong. The Red Sox should turn to free agency and landing Bregman would be a perfect next step.
Craig Breslow noted earlier in the week that the team is looking into free agency, although they “haven’t lined up yet.”
“It’s not a deliberate or intentional decision to close off one pathway in favor of another,” Breslow said, as transcribed by Cotillo. “We haven’t signed a free agent yet. That’s not because there aren’t free agents that we’ve been engaged in or because there aren’t really desirable targets in the free agent markets. We just haven’t lined up yet.”
The obvious next step is Bregman. Then, this team will really look like a contender.
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