The Red Sox are staring at an uncertain offseason, and the tension is not limited to just Alex Bregman’s opt-out clause. As the team attempts to balance its payroll and stay competitive in a tight AL East race, another vital star’s future looms large—one that could redefine the Red Sox’s infield core heading into 2026.

That star is shortstop Trevor Story. The MLB veteran, signed to a six-year, $140 million deal, who now faces a career-defining choice. The story carries an opt-out clause enabling the star to walk away from the final two seasons and $50 million after this season. The Red Sox could react by activating a 2028 club option worth three seasons and $75 million or decline and pay a $5 million buyout. Trevor Story’s decision comes as the star is finally enjoying a healthy season after two injury-plagued campaigns, batting .258/.305/.424 overall and .287/.337/.498 over the last three months.

While his resurgence is a positive development, it complicates the team’s offseason planning. If Trevor Story opts out, the management needs to decide whether to invest largely in a veteran approaching his mid-30s with a history of shoulder and elbow surgeries—and risk losing their reliable infielder just as they face potential turnover with Alex Bregman.

However, Trevor Story remains focused on the present. “It’s not even in my mind, to be honest with you,” he said to the Boston Globe’s Tim Healey. “I’ve been so locked in on the daily process and just what it takes to win each night. Those things are dealt with in the offseason”, the star added. However, behind closed doors, concern lingers: Can the Red Sox afford to lose Bregman and Story in the same winter? Would Story command a market given his injury history? Or could the team utilize that as leverage to retain him at a discount?

Ultimately, Trevor Story’s decision highlights more than just a deal clause—it is a litmus test for the Red Sox’s long-term approach. Does the team commit to a veteran leader showing signs of a comeback? Or will the team pivot toward a younger and cost-controlled core? The answer could hinge on how Story finishes this season and whether the team’s management believes its championship window remains open. Either way, with two cornerstone stars holding the keys to their futures, the team could be headed for the most pivotal offseason in recent memory.

While the Red Sox’s offseason decisions remain uncertain, the present-day spotlight shines squarely on the team’s ace, who is making waves in the most competitive individual race.

Garrett Crochet’s late-season surge tightens the AL Cy Young race

Former MLB star Mark DeRosa’s current statement on MLB Network has added serious intrigue to the AL Cy Young race. He highlighted that while Tarik Skubal has been the favorite for much of the season, the star’s current stumble — surrendering a pivotal grand slam to the A’s Shea Langeliers — could have cracked the door open. However, Garret Crochet has been flawless in pressure-packed games, highlighting not just dominant strikeout stuff, but also the poise of a seasoned veteran. The star’s current gem against the Yankees, where Crochet tossed seven shutout innings, has elevated his standing in a race that once looked settled.

For the Red Sox, Crochet’s rise is not just related to individual accolades; it is a boost to the team’s October ambitions. With the Red Sox fighting for playoff positioning, having a Cy Young-caliber star anchoring the rotation could be the difference-maker in a tight Wild Card race. DeRosa’s analysis highlights just how effective Crochet has become — transforming from a promising young star into a powerful team cornerstone. If the star continues this trajectory, he will not just challenge Skubal for the Cy Young; he could carry the team deep into October, rewriting the team’s 2025 narrative.

Trevor Story’s situation perfectly encapsulates the uncertainty related to the Red Sox’s future. The star’s talent is undeniable; however, patience is running thin as the Red Sox weigh outcome against expectations. Whether the star rebounds and becomes a symbol of missed scope, his story could define the team’s direction.