
It’s a day that ends in “y.” Therefore, we are back to give you an update on the Alex Bregman free agent saga as it relates to the Boston Red Sox.
Luckily for Red Sox Nation, it’s another positive update from one of the sports’ most trusted voices.
On Tuesday morning, ESPN’s Buster Olney had this to say in his latest column title “MLB free agency intel: Latest on Bregman, Tucker, more:”
“The Boston Red Sox want Bregman and have signaled a willingness to pay him big money -- perhaps something in the range of what the Tigers offered him last spring, a six-year, $171.5 million deal.”
This piece of reporting from Olney supports what he said on Toronto radio on Friday.
“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.”
Six years and $171.5 million would constitute “aggressive,” in my book!
It’s a departure from everything the organization has done, or hasn’t done, this offseason, as Boston is one of only two teams to not sign a single free agent this hot stove season.

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That other team is the Colorado Rockies. Which makes sense, because they’re…the Rockies.
That Boston has swung-and-missed on multiple big name free agents like Pete Alonso and Kyle Schwarber has been a cold, hard reminder of how this team does business in the post-Mookie Era. They’re willing to extend themselves, but only on their terms and only if the team is operating within the confines of the luxury tax that they’re comfortable with.
This new deal for Bregman at an AAV of $28.5 million would, by some projections, push the Red Sox past the first Competitive Balance Threshold. There’s been plenty of reporting to suggest that Boston was comfortable with that financial setup for 2026.
And while no one should be complaining about the Red Sox wrapping up Bregman at that number and term, there is room to sigh in frustration that this feels like the only “big money” deal Boston will be signing themselves up for this offseason.
As Alex Speier brilliantly laid out, Craig Breslow seems more-than-content team building through trades rather than free agent acquisitions.
Will the fan base be content with that as his modus operandi if the team is bounced in the Wild Card Round again this postseason?
That’s TBD, but “yes” is the betting favorite in Vegas at -100000.

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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.