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Alex Bregman’s $40M Red Sox Contract Could Be Last Hurdle Before Free Agency Shakeup

Alex Bregman signed a three-year contract with the Boston Red Sox before the 2025 season, which includes opt-out options after the 2025 and 2026 campaigns. These clauses give Bregman control of his career trajectory and place the Red Sox in a tricky situation as they attempt to secure his long-term services.

Bregman may choose to re-enter free agency following this season, especially considering his strong performance, despite experiencing some downtime due to a right quad injury. The presence of these opt-outs means the Red Sox must carefully evaluate their approach before Bregman’s potential market re-entry.

Evaluating Bregman’s Standout Performance in the 2025 Season

This year marks one of the best stretches in Bregman’s professional career. He is currently batting .301, the highest mark he’s maintained if he finishes the season above a .296 average. Although Bregman’s peak season in 2019—when he finished second in MVP voting behind Mike Trout—showcased more power and a higher on-base percentage, his 2025 metrics reveal improvements in other areas.

The strength behind Bregman’s hits is particularly notable this year. His average exit velocity is 90.7 mph, surpassing his previous best of 89.4 mph. Additionally, his hard-hit percentage climbed to 46.5% in 2025, well above the 40.5% recorded in 2024. His barrel percentage, a key indicator of extra-base hit potential, is 8.8% this season—markedly better than his previous high of 7.6% in 2018. These advanced metrics will be heavily weighed by teams should Bregman opt out and enter free agency.

Alex Bregman
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“Alex Bregman’s first season in Boston has been a wild success, but is he more valuable than other third basemen?”

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At 31 years old, turning 32 in March 2026, Bregman enters the latter half of his career. He is likely to seek a long-term contract, aiming for stability and security after not securing the desired deal during his initial free agency period last year. Analysts predict he will test the market again, where he could attract more lucrative offers.

Financial Landscape and Contract Market Challenges for Bregman

The current deal Bregman holds with the Red Sox carries an annual value of approximately $40 million across three seasons, including deferred payments. Market evaluations estimate his true value around $26.4 million annually, with projections suggesting a potential six-year contract if negotiations succeed.

Age stands as a significant factor affecting Bregman’s contract prospects. Over the past decade, only a few players aged 32 or older—namely Lorenzo Cain, Freddie Freeman, and DJ LeMahieu—have secured five-year deals. While Freeman’s performance with the Dodgers remains highly regarded, longer contracts for players of this age have shown mixed results with other clubs like the Brewers and Yankees. Bregman’s high caliber as a player may improve his chances, but teams will consider these precedents carefully.

Red Sox’s Urgency to Retain Bregman Amid Organizational Changes

Boston faces an urgent need to retain Bregman, particularly after trading away Rafael Devers, who was the previous face of their franchise and held the primary third baseman role before Bregman’s arrival. Devers’ departure, combined with existing roster shifts, leaves the Red Sox with a critical void at third base. Losing two top-tier players at the same position within a year challenges the team’s long-term competitiveness.

For the Red Sox, securing Bregman to a long-term contract before he hits free agency again may be the most viable way to avoid further disruption. The timing and structure of such a deal could determine the team’s stability and prospects as they head into the coming seasons.

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