Cubs avoided the Alex Bregman contract nightmare now haunting the Red Sox

Bregman has been great but the Red Sox may be in line for a massive L.

Jordan Campbell

Cleveland Guardians v Boston Red Sox / Winslow Townson/GettyImages

The Chicago Cubs' failed pursuit of Alex Bregman defined the end of their offseason, and while it seemed to have been an egregious mistake as the first half of the season was playing out, Matt Shaw's emergence since the All-Star break has taken the sting out of the fact that Bregman landed with the Boston Red Sox. It was an aggressive measure by the Red Sox to ensure they landed Bregman, but it may be one that they now regret.

Jeff Passan had an early look at this winter's free agents, and no surprise, he believes Bregman is going to opt out of the three-year deal he signed with the Red Sox.

"Because his deal included opt-outs after each of the first two seasons, Bregman could be playing elsewhere in 2026. Barring an injury or catastrophic slump, he will opt out and join Tucker and Schwarber in a clear top tier among this winter's free agents."

Cubs dodged a scary Alex Bregman contract fate now hitting Boston

Among the factors that made the Red Sox's offer a more compelling deal for Bregman than the Cubs' reported offer was the fact that he can test free agency after this season and next season. With a 131 wRC+ and 16 home runs in 95 games played this season, and backed by Scott Boras as his agent, testing free agency feels like a lock for Bregman.

Passan mentions that the Red Sox are interested in bringing Bregman back, but money could be the reason it doesn't happen. It's a painful reality facing the Red Sox, considering Bregman's arrival was what ignited the drama that eventually led to Boston trading Rafael Devers.

Fortunately, Bregman's likely free agency shouldn't suffocate the Cubs' offseason like it did last year. Shaw has proven to be the answer at third base, and after offensive adjustments in the second half, is already appearing to be a breakout candidate in 2026. For the first time in several years, it would seem the Cubs are entering the offseason with a definitive answer at third base.

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Jordan Campbell

For nearly 15 years, Jordan has been a workhorse across the FanSided network - including being the inaugural site expert for Cubbies Crib, as well as a stop at Da Windy City as the site expert. In addition to returning to be a Co-Site Expert at Cubbies Crib, Jordan was previously the Site Expert at Bear Goggles On. In the years since, Jordan has joined FanSided's full-time team, serving as a staff writer for the MLB division. Jordan's work can be seen across the MLB division, including a consistent presence on our Cubs, Twins, Astros, and Tigers sites. Since 2010, Jordan has dedicated his craft to providing insightful commentary on all things Chicago sports, and he has enjoyed his venture into all things Major League Baseball.