Why Red Sox Could Soon Part Ways With Alex Bregman, Per Insider

Are the Red Sox gun-shy about a long-term deal?

Aug 27, 2025; Baltimore, Maryland, USA; Boston Red Sox third baseman Alex Bregman (2) gestures on the field before the game between the Baltimore Orioles and the Boston Red Sox at Oriole Park at Camden Yards. Mandatory Credit: James A. Pittman-Imagn Images | James A. Pittman-Imagn Images

Alex Bregman's free agency will command the attention of Boston Red Sox fans far and wide for the second straight offseason.

After opting out of $80 million over the next two years earlier this week, Bregman is looking for a long-term deal heading into his age-32 season, which he knows is probably the last time he'll have teams willing to commit to him for five, six, or maybe even seven years.

Those commitments were there last offseason, namely from the Detroit Tigers and Houston Astros, but not for the dollar amount Bregman was seeking. The Red Sox, though, were only willing to commit to him for three years. Did having him around for a season change that calculus?

Insider suggests Red Sox could be unwilling to commit

Aug 22, 2025; Bronx, New York, USA; Boston Red Sox third baseman Alex Bregman (2) hits a fly ball against the New York Yankees during the seventh inning at Yankee Stadium. Mandatory Credit: Gregory Fisher-Imagn Images | Gregory Fisher-Imagn Images

Jim Bowden of The Athletic cast serious doubt on that front on Wednesday.

Bowden wrote an offseason preview based on conversations with all 30 front offices, and one of his takeaways for the Red Sox was that a long-term commitment for Bregman was far from guaranteed.

"The Red Sox loved their time with Alex Bregman and appreciated all he did on and off the field. That said, I’m not sure they’ll be willing to commit to Bregman on a long-term contract at his market price. If they don’t, expect them to let rookie Marcelo Mayer take over at third base with Trevor Story staying at shortstop."

Projections for Bregman's free agency tend to be either five or six years and rest somewhere between the $150 million and $180 million marks. If the Red Sox won't meet the minimum thresholds there, they can kiss the three-time All-Star goodbye, but if they're in the mix, it's hard to speculate on what other offers will be out there this time around.

What we do know is that Bregman turned down $171.5 million last winter from the Tigers, and $156 million from his old team, the Astros, who pivoted to trading for Isaac Paredes to fill third base.

With a host of other potential suitors to worry about, like the Chicago Cubs, Seattle Mariners, and Philadelphia Phillies, the Red Sox could be sending signals already that their year with Bregman was all they'll get.

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