The Boston Red Sox have been most consistently linked to two big-name free agents this winter: Alex Bregman and Bo Bichette.
Bregman has been the talk of Boston for weeks, as he should be. He’s the most seamless fit for an organization in need of one more bat. ESPN’s Buster Olney reported on Tuesday that Boston has “signaled a willingness” to hand Bregman a large contract. As rumors around Bregman have increased, Bichette has been the other guy linked to Boston, mainly as a secondary option.
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Bichette has spent his entire big league career to this point as a member of the Toronto Blue Jays and has consistently said publicly he wants to stick around with the organization. While this is the case, The Athletic’s Mitch Bannon reported on Tuesday that he is “increasingly unlikely” to return to Toronto.
The Red Sox have options
“The Toronto Blue Jays remain linked to All-Star hitters Bo Bichette and Kyle Tucker,” Bannon wrote. “Although league sources said the Jays have increased their efforts to recruit Tucker, who remains a roster fit after the signing of Japanese slugger Kazuma Okamoto, a reunion with Bichette appears increasingly unlikely…
“Throughout the 2025 season, Bichette consistently expressed his desire to stay in Toronto and play alongside his fellow franchise mainstay, Vladimir Guerrero Jr. While some in the Blue Jays organization remain advocates for signing the 27-year-old Bichette, the club’s infield as currently constructed appears crowded. It would be seemingly impossible to find regular reps for all of Bichette, Okamoto, Andrés Giménez and Ernie Clement. The Jays will likely stay in touch with Bichette’s representatives as free agency remains fluid and plans evolve.”
This is very intriguing from the Red Sox’s perspective. Bregman was consistently linked to the Blue Jays, but Bannon reported earlier in the week they no longer as likely for him either. The Arizona Diamondbacks, who also have been linked to Bregman, also had a bit of cold water thrown on their pursuit by The Athletic’s Ken Rosenthal.
If Toronto and Arizona actually aren’t involved — or at least to a lesser extent — that would help Boston’s chances in the Bregman derby as the only other team consistently linked to him has been the Chicago Cubs. For Bichette, if the Blue Jays are unlikely to land him, that could give the Red Sox an option there as well.
Landing either Bregman or Bichette would be huge for the organization. At this point, the markets for both aren’t fully defined and options seem to be dropping. Now, we just need one of them to drop into Boston’s lap.
More MLB: Alex Bregman Market Continues Shifting In Red Sox’s Favor