Back in late June, Alex Bregman’s agent Scott Boras said that his client was “always open to any conversation” about a longer-term agreement with the Red Sox. This created the impression that an in-season extension between the two sides was perhaps possible, though Bregman seemingly put an end to that idea when speaking with the Boston Globe’s Tim Healey today. While Bregman is “obviously…open to talking” at season’s end, the third baseman stressed that “for the next few months, I’m just really focused on the baseball. I’m just focused on trying to do what I can to help this team win and get into the playoffs. I feel like that’s where my head and mind need to be.”
Most players adopt this same stance with extension negotiations, preferring to have any deals finalized either prior to Opening Day or just after (if talks were almost but not quite completed by the first game). That said, there have also been plenty of in-season extensions over the years, as naturally each player has a different set of circumstances that can impact a long-term deal. For instance, the Red Sox completed a major extension just a few days ago with Roman Anthony, as the rookie sensation locked in the first fortune of his pro career by signing an eight-year contract that will pay him at least $130MM.
It is more rare to see an established veteran sign a new contract so close to free agency, so it isn’t surprising to see Bregman choose to put negotiations aside until Boston’s season (and what he hopes is a deep playoff run) is complete. Bregman signed a three-year, $120MM free agent deal with the Sox last winter that contains opt-out clauses after each of the first two seasons. That means Bregman can bank his $35MM salary from 2025 and leave the remaining money on the table in order to pursue a richer and longer-term commitment in another trip to the open market this offseason.
Bregman’s first season in Beantown was interrupted by a quad strain that kept him out of action for just shy of seven weeks. That significant absence notwithstanding, there is little doubt Bregman will indeed trigger his opt-out clause, as he is hitting .298/.380/.531 with 14 homers over 313 plate appearances in a Red Sox uniform. This translates to a 148 wRC+ that would be Bregman’s highest since his 167 wRC+ during the 2019 season with the Astros — Bregman finished second in AL MVP voting during this high point of his outstanding career.
Red Sox chief baseball officer Craig Breslow raved about Bregman during a radio interview in June, describing the third baseman as “everything we could have asked for both on the field but also in the clubhouse from a leadership standpoint. Not just in the way he’s helped younger players and our staff but in the ways that he’s helped me and many of us in the front office.” This praise of Bregman has been echoed by teammates and manager Alex Cora, leaving no doubt of Bregman’s quick impact on a young Red Sox team that is in the thick of the postseason race.
It would certainly seem that the Sox are willing to offer Bregman a lucrative deal that tacks a few more years onto his current contract (or overwrites it entirely) in order to get him to forego his opt-out decision. Bregman and Boras went into the 2024-25 offseason reportedly looking to land a $200MM guarantee, so speculatively speaking, perhaps a five-year, $165MM extension might be enough to get things done.
Such a deal would commit Bregman to the Red Sox through his age-36 season, give him the overall $200MM payday he was seeking in the first place, and perhaps get more money into his bank account a little sooner, depending on how this hypothetical contract is structured. Bregman’s current deal contains $60MM in deferred money, so Bregman is only receiving $20MM of his $35MM salary for 2025. Then again, Bregman could be open to deferrals since such an arrangement lowers the luxury tax hit of his contract, thus giving the Red Sox more flexibility in spending more on acquisitions or in locking up other players to extensions.
There are some parallels to Matt Chapman’s situation here, even though Bregman apparently won’t be following his fellow Boras Corporation client in signing an extension before the season is over. Chapman signed a three-year, $54MM deal with the Giants during the 2023-24 offseason that also contained two opt-out clauses, and then worked out a new six-year, $151MM extension last September.
It was surprising to see Chapman and Boras work out such a deal before even testing the market, especially when Chapman was so close to free agency, yet Chapman’s desire to stay in the Bay Area helped pave the way to a new agreement. As much as Boras has the reputation of “pushing” his clients towards the open market, the agent has negotiated plenty of high-profile extensions during his long career, so it shouldn’t at all be taken as a given that Bregman could be playing elsewhere in 2026. Indeed, given how much mutual interest there seems to be between Bregman and the Red Sox, it may be more likely than not that Bregman could indeed find himself as a Fenway Park cornerstone.
