The Red Sox offseason puzzle keeps getting more complicated. Third base has turned into a question mark with Alex Bregman testing the free agency waters, searching for his next long-term home. Meanwhile, the shortstop situation had fans equally nervous, with a $140M veteran whose contract structure left the door open to a potential departure. But fresh intel from someone close to the organization suggests Red Sox Nation can take a breath. At least one piece of this uncertain winter might be falling into place.

Trevor Story’s contract situation has been hanging over Fenway like storm clouds since their postseason run came to an end. The 32-year-old shortstop has two years and $55M remaining on his deal, but there’s a catch that’s been fueling speculation all season.

He can opt out and become a free agent, hitting the open market. That possibility alone has kept Boston’s front office planning for multiple scenarios.

Chris Cotillo of MassLive brought some much-needed clarity to the situation. “As of mid-September, Red Sox decision-makers expected Story, who has two years and $55 million left on his contract, to opt in,” Cotillo reported.

He further mentioned, “There’s a chance he’d make more than that on the open market, but there’s also a feeling that he feels loyalty — and appreciation — toward the Red Sox after missing most of the first three years of the deal.”

His insight points to something deeper than just contract math—there’s a human element at play that numbers don’t capture.

Story’s comeback from the injury changed the whole dynamics for the clubhouse. He was hitting .263 with 25 home runs and playing great defense and power in the center of Boston’s infield.

Not only that, but as of September, he was also leading the team with 25 homers and 28 Stolen Bases. On the plate, he was playing up to his potentia,l and in the locker room? Well, his presence was equally important.

Story’s become an experienced voice in the clubhouse, along with Jarren Duran and Alex Bregman. His teammates say that his enthusiasm, sense of responsibility, and modest competition are what keep the locker room together. Story’s leadership goes beyond the field for a team that needs to balance experienced and young players. It’s a tone that Boston can’t afford to lose.

As per the insider, he isn’t going anywhere, but if he changes his mind? Then what’s the next possible solution for BoSox?

If the leader walks, who fills the void at Shortstop?

If he leaves, there will be a big hole at shortstop, which would make the Red Sox have to reevaluate how they set up their infield and who is in charge going into 2026.

Bo Bichette would be one of the first names that came to mind. He is perhaps the greatest shortstop on the free-agent market. The Toronto standout has great bat-to-ball skills, solid fielding, and a proven track record in the AL East.

Signing Bichette would keep Boston in the running and keep the left side of the infield stable with veterans. But his price ($200M approx.) might make it hard for Boston to stay within its budget, especially since it needs to fill other roster gaps.

This would be a risky yet ambitious move.

The Red Sox might also look inside and turn to Marcelo Mayer, a highly rated infield prospect. Mayer has good defense, fluid mechanics, and more power at the plate, but giving him the starting job would mean some growing pains.

If Alex Bregman leaves as well, Boston’s infield would become younger and less experienced. This would be a big change from the reliability that Story and Bregman brought in 2025.

With Mayer in the picture, the Bo Sox lineup will be full of young bloods. Instead of relying on senior steadiness, the squad might build around Duran, Casas, and Mayer.

That plan may get the players excited, but it would require patience and leadership from both the front office and the dugout.

If Story quits, Boston’s next step will show whether it wants things to stay the same or is ready to make a big change for the better.