The Boston Red Sox’s season just ended, but it’s already time to start thinking about the offseason.
One of the biggest questions facing the Red Sox this winter is whether the left side of its infield — Alex Bregman and Trevor Story — will opt out and test free agency.
While Story opting out of his contract is considered unlikely due to his age (32) and recent injury history, Bregman opting out of his deal appears far more likely.
“According to a source, it’s a near certainty that Bregman will opt out and test free agency for a second straight year, this time without a qualifying offer attached to him,” MLB.com’s Mark Feinsand reported on Friday.
Bregman, who was also a free agent last offseason, signed a three-year, $120 million deal with Boston, turning down more guaranteed money from the Detroit Tigers and Houston Astros in exchange for a higher AAV and more flexibility.
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Coming off a strong 2025 where he batted .273/.360/.462 with 3.5 WAR and his highest OPS (.821) since 2019, the All-Star third baseman appears likely to test the market again in search of a larger deal. He is a Scott Boras client, after all.
Fortunately for the Red Sox, Feinsand reports that many around the industry still expect Bregman to return to Boston, even if he does opt out.
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“The consensus around the league is that a Bregman-Boston reunion remains the most likely scenario,” Feinsand writes.
Bregman enjoyed playing for the Red Sox this year and had a successful season on both an individual and team level. He also clearly wants to be in Boston, as evidenced by his taking less money to play there last winter.
Meanwhile, the Red Sox presumably want Bregman back. In addition to his strong performance on the field, he was also a highly respected clubhouse leader who helped many of the young players around him improve. With his veteran presence and all-around skills, he’s a perfect fit for Boston.
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Bregman made a good impression on the Red Sox this year, and vice versa. That should give them a leg up if he does test free agency, which appears increasingly likely.
