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Cubs Land Bregman Prize While Red Sox Questions Mount

The Cubs are continuing to burnish their roster after landing free-agent Alex Bregman, while the Red Sox missed out on one of their top offseason priorities.

Sep 24, 2025; Toronto, Ontario, CAN; Boston Red Sox third baseman Alex Bregman (2) hits a single against the Toronto Blue Jays in the first inning at Rogers Centre.
Dan Hamilton-Imagn Images

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Two stalwart MLB franchises are in a state of heightened transition after veteran third baseman Alex Bregman reached a five-year, $175 million free-agent deal with the Cubs. 

The pact with Chicago, including $70 million in deferrals, followed a single season in Boston, after which Bregman opted out of the final two seasons of a three-year contract to reenter free agency. Despite an injury-afflicted campaign with the Red Sox that included just 114 games played, Bregman elevated his market considerably. 

Bregman’s contract includes no opt-outs and a full no-trade clause. With those elements, as well as additional money, the new deal with the Cubs is a marked upgrade over a four-year, $115 million deal the team offered the 31-year-old last offseason.

Boston is the lone MLB franchise to not have signed a free agent this offseason, and retaining Bregman had been a key priority for the Red Sox entering the offseason. The news of his departure arrived just after the conclusion of the club’s offseason Fenway Fest fan event on Saturday, which amplified an already nervous vibe among many Red Sox faithful.

Appearing at Fenway Fest, Red Sox president and CEO Sam Kennedy pointed to a series of contractual extensions the team has made in the last year including to star pitcher Garrett Crochet and second baseman Kristian Campbell.

“I think it’s just important to look at the facts,” Kennedy said. “If you go back a year ago, this date last year, I believe our organization has taken on close to $500 million in contractual commitments. … That’s just a fact. We cannot and do not try to control social media narrative. We understand that talk radio is ablaze with opinions and ideas. That’s what makes this the best place in the world to be, to live, and to operate in baseball.”

Kennedy, however, did not mention a prior trade of third baseman Rafael Devers that shed more than $250 million in future payroll, and was made in part with an eye toward gaining greater financial latitude for free-agent markets such as this one.

North Side Elevation

Bregman’s contract is the richest in Cubs history on an annual basis, and continues an active offseason for the club as it looks to catch up to the archrival Brewers—who claimed the NL Central division title last season and eliminated the Cubs in the playoffs. 

The Cubs also recently brokered a trade with the Marlins to bring in hard-throwing pitcher Edward Cabrera for three prospects. With the club’s chances of retaining outfielder Kyle Tucker, by many accounts the top available free agent, signing Bregman brings another impact bat to the lineup, along with widely lauded leadership skills and plenty of postseason experience, burnished through a prior run with the Astros that included two World Series titles. 

The signing of Bregman also added to a particularly epic sports Saturday for Chicago that included the Bears’ playoff win over the hated Packers, and victories by the Bulls and Blackhawks. 

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