What Alex Bregman considers a ‘very high priority’ in free agency, plus one factor that might hurt Red Sox

In late June, I caught up with Red Sox third baseman Alex Bregman in the home dugout at Fenway Park in an effort to ask about his future, contract status, extension talks and long-term fit in Boston. Among the usual platitudes and clichés came one answer that really stood out.

Bregman said he was willing to listen to “anything” the Red Sox had to say about long-term talks, adding that he “expected to love playing here (in Boston) and ”definitely (have) loved playing here.” Then, I asked him if it was a goal that his next deal, in some form or fashion, would allow him to find a place he could call home for the rest of his career.

“For sure. For sure,” said Bregman, growing serious. “That’s definitely a very high priority.”

It’s no secret that Bregman’s first go-around in free agency wasn’t perfect. He prioritized fit and market over guaranteed money, declining a six-year, $171.5 million guarantee from the Tigers and a four-year, $120 million deal with the Cubs (that included two opt-outs) to sign a short-term, high-value pact with Boston. In effect, Bregman’s deal with the Red Sox was worth $40 million (with heavy deferrals) over one season with back-to-back player options that could grow the total value to $120 million over three years. Now that he intends to opt out, it’s clear Bregman and his agent, Scott Boras, were comfortable taking a “bridge” contract in hopes that Bregman would play well enough to take another crack at the open market after the season.

“Certainly, I told John (Henry) and Tom (Werner) that I wanted the 10-year contract,” Boras said on February 16, when Bregman was introduced as a member of the Red Sox. “Always, in these settings, the dynamic is sometimes fluid. The main thing is that this agreement allows for everyone to get to know one another.

“I can basically give the player optionality and some guarantee. The club, then, had an avenue not to often the long-term but then pursue the bridge contract with the understanding it allowed us time for discussion and opportunity to remain in the organization. If not, then move in another direction.”

This time around, things will likely be different. Bregman is likely heartened by the fact he was able to change organizations for the first time in a decade and not only fit in seamlessly to a new culture, but still produce. But as the father of two young boys who was a major part of the Houston community during his nine years with the Astros, Bregman clearly wants stability. He will be 32 in March, so a six-year deal would take him through his age-37 season and a seven-year deal would take him to 38. It’s that kind of deal the Boras camp will almost certainly seek, and the fact Bregman is no longer tied to the qualifying offer will certainly make it more palatable for other clubs to extend offers his way.

Teams value their draft picks more than ever, and it’s indisputable that Bregman’s market was hurt by the fact teams had to sacrifice a draft pick (in Boston’s case, their second-rounder at No. 54) to sign him after he declined the qualifying offer a year ago. This year, as a player who has already gotten the qualifying offer once in his career, he’s not eligible. So Bregman, like fellow top free agent slugger Pete Alonso, won’t be tied to a draft pick. Kyle Tucker, Kyle Schwarber, Bo Bichette and others will be as first-time QO recipients. The incumbent team always holds a slight advantage in these cases as the only team that wouldn’t need to sacrifice a pick to sign a qualified player; for example, the Phillies wouldn’t need to do so to re-up Schwarber this winter. The playing field for Bregman, is now even, though, and that’s something that can only help his value.

There are teams who might be scared off by Bregman’s age — as well as how it meshes with his hard-nosed approach to playing — as well as the fact that soft-tissue injuries have cost him significant time in two of the last five seasons. There are also teams that might be willing to overpay for his high floor, championship pedigree and leadership intangibles that the Red Sox benefited from in 2025. Boston will have to decide what kind of commitment makes sense — and how far the club wants to extend itself not just when it comes to dollars, but also years.

With big-market behemoths (Yankees? Phillies? Cubs?) and some smaller-market clubs looking to take the next step (Detroit? Kansas City? Seattle?) potentially in the mix for Bregman, he’s going to get a bunch of different-looking offers. This time around, a short one likely won’t get the job done.