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Craig Breslow finds himself navigating treacherous waters as the Red Sox’s Chief Baseball Officer watches Alex Bregman’s stellar performance potentially price the star third baseman out of Boston’s future. With Bregman holding opt-out clauses after both 2025 and 2026 on his three-year, $120 million deal, every spectacular play strengthens his case for a bigger payday elsewhere, leaving Breslow caught between celebrating success and dreading its financial consequences.

The clubhouse chemistry surrounding Bregman has become impossible to ignore, particularly from teammates who witness his daily impact firsthand. Red Sox pitcher Lucas Giolito experienced this support system personally, describing how Bregman approached him after a recent outing with crucial mechanical advice. The veteran pitcher’s appreciation runs deep for what he calls the team’s collaborative environment, where players actively help each other improve rather than staying isolated in their roles.

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Giolito’s testimony reveals the true value Bregman brings beyond statistics. “This is the best I’ve been around as far as guys helping each other out. Bregman is a real treasure in that aspect,” Giolito explained, recounting how the third baseman noticed opposing hitters had picked up on his changeup timing.

“He comes to me after my game last night, and he’s like, ‘Hey, you’re doing this out of the windup. I think they had your changeup’….You feel that extra layer of support… It’s not like you go out there as a pitcher and you’re on an island.” The pitcher emphasized how rare such comprehensive team support feels, noting that Bregman’s leadership creates a “more cohesive team environment” where everyone actively contributes to collective success.

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Breslow has remained diplomatically tight-lipped about extension discussions, recently telling reporters, “I think it’s best to keep that internal right now” when pressed about contract talks. Meanwhile, Bregman himself has indicated he prefers waiting until the offseason to engage in serious negotiations, leaving both sides in a delicate dance. With the Red Sox competing for playoff positioning and Bregman’s leadership proving invaluable daily, Breslow faces the ultimate front office dilemma: how to retain a cornerstone player whose excellence may have already outgrown the organization’s financial comfort zone.

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Bregman’s Success Complicates Red Sox’s Future Plans

The Boston Red Sox find themselves in an unexpected playoff hunt after pulling off one of the year’s most stunning moves – shipping Rafael Devers to San Francisco. While fans initially questioned the decision, Boston’s success has largely stemmed from their offseason coup in landing Alex Bregman on a three-year, $120 million contract that includes crucial opt-out clauses after each season.

Bregman’s All-Star campaign has many expecting him to exercise that opt-out option when the season ends. The third baseman’s stellar performance has MLB insider Jon Heyman projecting he could command a $200 million payday on the open market. “This is not a knock on Yoshida as he has been better than many fans (and probably the Red Sox) give him credit for,” FanSided’s Eric Cole recently observed about the team’s roster construction challenges.

What’s your perspective on:

Can the Red Sox afford to lose Bregman, or is he too valuable to let go?

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Boston faces a financial puzzle even with Devers’ massive contract off the books. The organization clearly wants to retain Bregman, but doing so might require some creative roster moves. Cole believes the key lies in moving Masataka Yoshida, noting that the designated hitter’s struggles translating his Japanese power numbers have created both a financial and positional logjam.

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The math makes sense from Boston’s perspective. Yoshida carries an $18.6 million annual commitment through 2027, and his 27 home runs across 250-plus MLB games pale compared to his consistent 20-plus homer seasons in Japan. Moving him would not only free up significant payroll space but also solve the DH logjam that’s been limiting the team’s roster flexibility. Whether the Boston Red Sox can pull off another surprising move remains the season’s biggest question.

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"Can the Red Sox afford to lose Bregman, or is he too valuable to let go?"

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