Alex Bregman’s year with the Boston Red Sox was a good one, but it ended on an ominous note.

Through mid-August, Bregman was one of the best players in Major League Baseball when healthy. A brutal final 35 games, however, dropped his season OPS to .821 in 114 games — good production, but not necessarily worthy of the $40 million salary he was making.

Now, the Red Sox must grapple with how much to pay a player who proved instrumental to the culture they’re trying to build, but wants a deal larger than some in the organization might be comfortable paying.

Sep 19, 2025; Tampa, Florida, USA; Boston Red Sox third base Alex Bregman (2) hits a home run during the third inning against the Tampa Bay Rays at George M. Steinbrenner Field. Mandatory Credit: Kim Klement Neitzel-Imagn Images / Kim Klement Neitzel-Imagn Images

On Sunday, insider Sean McAdam of MassLive discussed Bregman’s upcoming free agency (assuming he opts out) and suggested that the star’s insistence five-year deal or more might be the point at which Boston would walk away from the negotiating table.

“(The Red Sox) love his contributions on and off the field,” McAdam wrote. “It’s an open question, however, whether the Sox will go dollar-for-dollar with other teams to retain Bregman.”

“Should Bregman attract offers of five or more years, ask yourself this: does the idea of paying Bregman better than $35 million annually at age 36 and 37 sound like something that would be approved by (principal owner) John Henry?”

Henry’s willingness to spend this winter will be the subject of a boatload of Red Sox conversations. After proving his appetite for massive contracts for Liverpool FC these last couple years, fans are hoping the billionaire’s baseball club can get back into the upper echelon of big-market teams.

That applies not only to the Red Sox’s pursuit of Bregman, but free-agent sluggers like Kyle Schwarber and Pete Alonso as well. Both of those two would be major additions to a lineup that didn’t have a 30-homer bat this season.

The Red Sox took a long time to sign Bregman last winter, and their unwillingness to give him a long-term deal was the key to the holdup. Could having him in the clubhouse for a year have changed their outlook?

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