Inside The Red Sox

Red Sox's First Move After Roman Anthony Extension Should Be Obvious

It's time to keep reallocating those savings...
Jul 28, 2025; Minneapolis, Minnesota, USA; Boston Red Sox third baseman Alex Bregman (2) celebrates his three run home run against the Minnesota Twins with left fielder Roman Anthony (19) in the fifth inning at Target Field. Mandatory Credit: Bruce Kluckhohn-Imagn Images
Jul 28, 2025; Minneapolis, Minnesota, USA; Boston Red Sox third baseman Alex Bregman (2) celebrates his three run home run against the Minnesota Twins with left fielder Roman Anthony (19) in the fifth inning at Target Field. Mandatory Credit: Bruce Kluckhohn-Imagn Images | Bruce Kluckhohn-Imagn Images

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Say what you will about Boston Red Sox chief baseball officer Craig Breslow's overall track record, but the man can broker an extension.

Brayan Bello and Ceddanne Rafaela last year. Kristian Campbell, Garrett Crochet, and now Roman Anthony this year. That's a total of $365 million shelled out in guarantees, with the potential for a lot more money to be made when factoring in club options and incentives.

Anthony's extension, which was first reported by ESPN's Jeff Passan on Wednesday, was the first major re-allocation of the money the Red Sox saved by trading Rafael Devers to the San Francisco Giants. And the next move Boston needs to make is all too clear.

Red Sox must lock up third baseman Alex Bregman next

Alex Bregman
Jul 20, 2025; Chicago, Illinois, USA; Boston Red Sox third baseman Alex Bregman (2) celebrates int he dugout after he hit a three run home run against the Chicago Cubs during the eighth inning at Wrigley Field. Mandatory Credit: Matt Marton-Imagn Images | Matt Marton-Imagn Images

As Anthony has blossomed into a star, it's no secret that he's taken a special liking to veteran third baseman Alex Bregman, who has become a clubhouse leader despite only arriving to the team in February. Now, Boston needs to make sure Anthony doesn't lose his mentor.

Bregman signed a three-year, $120 million contract, but he can opt out and re-enter free agency this winter, without the qualifying offer dissuading teams from losing a draft pick if they sign him. It seems more likely than not that if nothing changes between now and November, Bregman will indeed hit the open market.

Both Breslow and Bregman have alluded to the fact that they'd love to work out something long-term, but there's been no report of substantive negotiations. The 31-year-old has repeatedly said how happy he and his family are in Boston, and there's no better ballpark to fit the three-time All-Star's pull-heavy right-handed swing.

Boston saved $254.5 million by unloading the full value of Devers' contract, with some of that money canceling out by eating about $30 million of reliever Jordan Hicks' contract. They gave just over half of that to Anthony, but there should still be more than enough left over to tack onto the $80 million they already owed Bregman if he were to opt in.

Here was what Bregman had to say about the possibility of an extension back on Jul. 14, according to Peter Abraham and Alex Speier of the Boston Globe:

"I think for me, I'm focused on playing good baseball and trying to help this team win games," Bregman said. "We're obviously open to hearing whatever the Red Sox have to say."

It's clear that Breslow's Red Sox can get a deal done when they've set their mind to making sure a player stays. Now is the time to lock in and bring Bregman (or more accurately, agent Scott Boras) to the negotiating table.


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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