In a move that has baseball fans buzzing, Trevor Story has decided to stay with the Boston Red Sox, opting into the remaining two years and $55 million of his contract. But here's where it gets intriguing: this decision comes after a rollercoaster few seasons for the veteran shortstop, marked by injuries, a stellar 2025 comeback, and a free agent market that might have tempted him to explore other options. So, why did he choose to stay? And what does this mean for the Red Sox’s future?
Published on November 4, 2025, by Chris Cotillo and Christopher Smith of MassLive, this update sheds light on Story’s commitment to the organization. The 32-year-old, who initially signed a six-year, $140 million deal in March 2022, had the option to test free agency after the 2025 season. If he had opted out, the Red Sox could have extended his contract by adding a $20 million option for 2028. Instead, he’ll earn $25 million annually for the next two seasons, with a $25 million team option and a $5 million buyout for 2028.
Story’s journey hasn’t been without challenges. After missing significant time in 2023 and 2024 due to major elbow and shoulder surgeries, he bounced back in 2025 with a strong performance: a .263 batting average, 25 home runs, and 96 RBIs across 157 games. This resurgence helped the Red Sox clinch their first postseason berth since 2021. But here’s the part most people miss: despite his elite defensive reputation, Story had a down year in the field in 2025, posting negative defensive metrics. Could this have influenced his decision to stay, or is he betting on a return to form?
The free agent market for shortstops was notably thin this year, with Toronto’s Bo Bichette as the standout exception. If Story had sought a longer deal, this landscape might have been a factor. Yet, he chose stability with the Red Sox, a team he clearly believes in. And this is where it gets controversial: was this a smart move for Story, or did he leave potential opportunities on the table? Let us know your thoughts in the comments!
Looking ahead, the Red Sox’s infield remains a puzzle. With Alex Bregman opting out and becoming a free agent, Boston faces questions at third base. Meanwhile, Story’s presence at shortstop could influence other roster moves, including a potential shift to second base if the team pursues other infield upgrades. First baseman Triston Casas is set to return from injury, and prospects like Romy Gonzalez and Marcelo Mayer are in the mix, but uncertainty looms at three of the four infield spots.
What’s your take? Is Story’s decision a win for the Red Sox, or should he have explored free agency? And how will Boston address its infield questions this offseason? Share your thoughts below—we’d love to hear your perspective!
