Red Sox's Toughest Contract Decision That Could Define the Winter

The Boston Red Sox should be taking a look at Adley Rutschman closely this winter.

Sep 23, 2026; Boston, Massachusetts, USA; Boston Red Sox catcher Adley Rutschman (31) hits a single against the Cleveland Guardians during the third inning at Fenway Park. Mandatory Credit: Gregory Fisher-Imagn Images | IMAGN IMAGES via Reuters Connect

It's going to be a long offseason for the Boston Red Sox. On paper, the roster arguably is better than it was at this point last year, but there are still decisions that need to be made. Plus, the Red Sox were knocked out of the playoffs early again. So, they have even more time to prepare ahead of the 2027 campaign.

There aren't a lot of decisions for the club to make when it comes to internal free agents. Sonny Gray's mutual option is the most obvious thing to follow. He has a $30 million mutual option that is sure to be declined. It would be great to then get a new deal done, but it's too early to know if the two sides will. With that being said, there's another contract situation that should have every fan's attention this winter: Adley Rutschman.

The Red Sox gave up an arm and a leg to acquire the All-Star backstop from the Baltimore Orioles ahead of the 2026 trade deadline. While some may question the deal, Rutschman is undoubtedly a star and was a positive addition to the organization overall in the second half. His bat wasn't going right away when he got activated off the Injured List, but he was excellent defensively and then got hot in September.

The Red Sox Should Extend Adley Rutschman

Sep 29, 2026; Bronx, New York, USA; Boston Red Sox starting pitcher Payton Tolle (70) reacts with catcher Adley Rutschman (31) and first baseman Willson Contreras (40) during a pitching change during the fifth inning of game one of the Wildcard round of the 2026 MLB Playoffs against the New York Yankees at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | IMAGN IMAGES via Reuters Connect

It took years for the Red Sox to significantly improve the catcher position, but they now have a star. Unfortunately, he's only under team control for one more season. After the 2027 season he will be a free agent. This winter, the Red Sox should do everything to prevent that from happening. With the amount the Red Sox gave up, if they were to only have the All-Star backstop for a little over one full season, it would be a disaster.

Boston should be prepared to offer the 28-year-old an extension this winter and see what happens. If the Red Sox are able to get a deal done with him this winter, it surely wouldn't be cheap, which could then impact how the club handles the rest of the offseason.

When Rutschman is healthy and at his best, he's a game-changer. And, he's young enough to fit this core into the future. Boston should be prioritizing an extension now, especially because the free agent class is very weak. Similar to guys like Garrett Crochet and Roman Anthony, Rutschman should be next in line for a new deal.