After months of waiting, an “aggressive” Red Sox offer may finally be shifting the offseason stalemate.
It has now been two full months since Alex Bregman opted out of his contract with the Red Sox, and the wait - both for the player and for fans - continues.
No signature. No resolution. Just the familiar hum of offseason uncertainty that seems to follow this organization whenever a cornerstone player reaches free agency. It’s old hack, at this point.
And yet, for the first time in a while, there’s legitimate reason to believe this standoff might finally be nearing its end.
On Friday, ESPN’s Buster Olney offered what was easily the most encouraging update Boston has received all winter on Bregman.
“I think Alex Bregman is gonna go back to the Red Sox,” Olney said on TSN 1050’s morning show. “From what I understand, the Red Sox have made an aggressive offer on him.”
That word - aggressive - matters, especially after Thursday’s report from MLB Network’s Mark Feinsand, who noted the Blue Jays and Diamondbacks appeared most aggressive in pursuing Bregman.
For fans bracing for another high-profile near-miss, that framing felt ominous.
Olney’s update reframes the entire conversation.
This is not Boston lurking on the outskirts or making a courtesy check-in. The Red Sox have stepped forward with an offer that, in Olney’s view, makes them the likely landing spot.
That tracks with what’s made sense all along.
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Bregman’s 2025 season in Boston wasn’t just a bounce-back - it was foundational. He stabilized third base, lengthened the lineup, and provided a steadying presence in a clubhouse that desperately needed one. The Red Sox don’t reach the postseason for the first time in four years without him. Removing that piece now wouldn’t just create a hole at third; it would unravel roster depth across the diamond.
There’s also the human element.
Both sides have been careful, but consistent, in expressing mutual interest in a reunion. Bregman liked Boston, and there’s been reporting to suggest that he wants to end his career there. The Red Sox liked what Bregman brought - on the field and behind the scenes. That doesn’t guarantee a deal, but it does make the silence easier to interpret.
Timing, too, matters here.
Spring Training is still six weeks away. Bregman didn’t sign until mid-February last winter. He opted to wait out the market before ultimately landing in Boston. Scott Boras has lived this movie before. Patience has long been part of his script.
The difference now is urgency and clarity.
If Olney is right, the Red Sox aren’t waiting anymore. They’ve put their best foot forward.
The ball, once again, is in Bregman’s court.
Should this saga end as many around the game expect, Boston’s offseason could finally close not with uncertainty, but with the return of its cornerstone. Right where he belongs.
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Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He's a senior digital content producer for WEEI.com, and a native of Lincoln, RI.