Inside The Red Sox

Red Sox CEO Drops Hints On Alex Bregman's Free Agency

How will Sox fans respond?
Aug 22, 2025; Bronx, New York, USA;  Boston Red Sox third baseman Alex Bregman (2) prior to the game against the New York Yankees at Yankee Stadium. Mandatory Credit: Gregory Fisher-Imagn Images
Aug 22, 2025; Bronx, New York, USA; Boston Red Sox third baseman Alex Bregman (2) prior to the game against the New York Yankees at Yankee Stadium. Mandatory Credit: Gregory Fisher-Imagn Images | Gregory Fisher-Imagn Images

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It's officially mid-January, and Alex Bregman has still yet to sign a new free-agent contract.

After the Boston Red Sox ultimately sealed the deal with Bregman last February, a lot of fans were hoping for a quicker resolution this time around. Bregman is seemingly the clear No. 1 item on the Red Sox's wish list, but even as other teams' threat levels have diminished, the Red Sox have yet to seal the deal.

It's an anxiety-inducing time for those hoping the Red Sox can sustain the progress they started to make with Bregman on the roster last year, and that prevailing emotion likely wasn't helped by the club's chief executive officer in the comments he made on Saturday.

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Sam Kennedy talks Bregman on Saturday

At Saturday's "Fenway Fest" event in Boston, CEO Sam Kennedy spoke to reporters and although he declined to reference Bregman by name, it was obvious that he was talking about the three-time All-Star third baseman when he emphasized that Boston still had time to make moves.

"Well look, there's, couple a couple things I would point out -- that we're still in January," Kennedy said, per Ian Browne of MLB.com. "And the rules of the road are there's no deadline here, to sign free agents.

"And I know there's been a lot of discussion about free agent signings or lack thereof, but obviously there's two ways to build a roster in the offseason, free agency and trades. So far, we've made a number of trades that we think will help the team. We’ve added significant payroll via trade, I think we've added more payroll [through trade}, roughly $40 million, than any other team."

If there's a place where Kennedy may have drawn the ire of Red Sox fans, it would be the implication that the team's moves to this point had been sufficient. Yes, the Red Sox have made three trades to improve the major league roster, but almost no one believes that the work is done with Bregman still unsigned.

But the Red Sox are taking too much heat at this point for being the only team not to spend a major league free agent, because there are only one or two free agents who have signed that would have filled a similar role to Bregman.

And as teams like the Toronto Blue Jays and Arizona Diamondbacks seem to be falling out of the running, the odds of Boston retaining Bregman seem high, even if it's taking too long.

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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@wtfsports.org