Boston Red Sox shortstop Trevor Story has a handful of question marks looming over his head this winter.

Will the two-time All-Star be the Red Sox's starting shortstop by the time the 2027 season rolls around? Will Boston switch him to a different position on the diamond, like second base or maybe even designated hitter? Or, could he end up being off the team entirely? It's going to be a long offseason and all of these options are at least realistic for the veteran.

MassLive.com's Chris Cotillo noted that if Boston does "go big for a long-term star shortstop" this winter, that will put Story's future in Boston "squarely in doubt."

"A massive shakeup could occur if the Red Sox decide to go big for a long-term star shortstop, should one become available," Cotillo wrote. "That puts Story’s future in the organization squarely in doubt, especially considering his contract status and the fact he was unable to build off a strong 2025 and instead went backwards (especially on the health front) in 2026."

Trevor Story Is Completely Up In The Air

Boston tried to do just that ahead of the 2026 trade deadline. Zach Neto of the Los Angeles Angels, CJ Abrams of the Washington Nationals and Elly De La Cruz of the Cincinnati Reds were all connected to Boston at times, among others. Story has one more season left on his deal for the 2027 season worth $25 million. Then, he has a $25 million club option for 2028.

Cotillo specifically noted that the middle infield is the biggest question mark on the diamond for Boston because there are so many different routes the Red Sox could go. Right now, Story and Curtis Mead would seemingly in line to start at second base and shortstop. But what about Franklin Arias? What about external additions? What about the depth guys, like Nick Sogard? There are a lot of decisions for Boston to make this winter. While attempting to predict what will happen, Cotillo did predict that Story's time in Boston will end this winter. That doesn't confirm it will happen, but it's a take from one of the most plugged-in Boston insiders out there.

When it comes to Story, there's no question about the talent that he has. When he is healthy, he can be a difference-maker offensively. The 2025 season was a perfect example of that. He hit 25 home runs, drove in 96 runs, stole 31 bases and hit .263 in 157 games played. He was a 4.1 WAR player. But that is the only season in his five-year run in which he played in more than 94 games. In 2026, he struggled out of the gate when he clearly wasn't at 100 percent. Then, he underwent sports hernia surgery and was awesome down the stretch, but he played in just 64 total games.

There aren't many avenues for the Red Sox to add offense. If the Red Sox were to move on from Story, that would open up shortstop for Arias — or an external addition. Then, you could also easily open up the designated hitter spot for another lineup addition.

It's hard to believe that Boston will find someone to take on that much money that's left on his deal. Right now, everything seemingly is on the table. Right when the World Series comes to an end, we'll start to see clubs around the league start to take steps towards concrete resolutions.