What Alex Bregman considers a ‘very high priority’ when it comes to free agency, more of a factor that could hurt the Red Sox

In late June, I met with Red Sox third baseman Alex Bregman in the dugout at Fenway Park, aiming to ask him about his future, the status of his contract, extension discussions and his long-term fit in Boston. Among the usual platitudes and clichés, one answer really stood out.

Bregman said he was willing to listen to “whatever” the Red Sox had to say about long-term discussions, adding that he “expected to enjoy playing here (in Boston) and “really loved playing here.” » Then I asked him if his next deal, in any way, would allow him to find a place he could call home for the rest of his career.

“Of course. Of course,” Bregman said, becoming serious. “It’s certainly 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, turning down a six-year, $171.5 million guarantee from the Tigers and a four-year, $120 million deal with the Cubs (which included two opt-outs) to sign a high-value, short-term pact with Boston. Indeed, Bregman’s deal with the Red Sox was worth $40 million (with hefty carryovers) over one season with back-to-back player options that could bring the total value to $120 million over three years. Now that he intends to retire, it’s clear that Bregman and his agent, Scott Boras, were comfortable with a “bridge” contract in the hopes that Bregman would play well enough to take another chance on the open market after the season.

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

“Basically, I can give the player an option and a certain guarantee. So the club had the option of not being too committed to the long term, but then continuing with the transitional contract, with the understanding that it gave us time to discuss and the possibility of remaining in the organization. If not, then go in another direction.”

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

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

Some teams might be spooked by Bregman’s age — as well as how that fits with his hard-nosed approach to the game — 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 pieces 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 stretch not only in terms of dollars, but also years.

With big-market giants (Yankees? Phillies? Cubs?) and some small-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 offers. This time around, a short version probably won’t do the job.