3 Dangerous Mistakes the Red Sox Must Avoid This Offseason

The Boston Red Sox has a lot of work to do with a long offseason ahead.

Aug 30, 2026; Bronx, New York, USA; Boston Red Sox outfielder Jarren Duran (16) runs off the field at the end of the seventh inning against the New York Yankees at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | IMAGN IMAGES via Reuters Connect

It's going to be a long time before Boston Red Sox fans see their team back in action again.

Boston's season ended on Sep. 30 by a score of 9-2 against the New York Yankees in the American League wild-card series. If all goes well and the 2027 season starts as planned without interference from the ongoing labor questions, Boston fans will have to wait until the end of March to see the club take the field again in a regular season game. If the collective bargaining agreement negotiations go poorly, it could be even longer than that.

Either way, it's going to be a long offseason for the Red Sox. What Boston does over the next few months will be the biggest determining factor on whether the club can contend for a title next year. With that being said, here are three mistakes the Red Sox need to avoid this winter.

No. 3. Continuing To Kick The Can On The Outfield Logjam

Sep 9, 2026; Boston, Massachusetts, USA; Boston Red Sox left fielder Jarren Duran (16) runs off the field during the sixth inning against the Los Angeles Angels at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images | IMAGN IMAGES via Reuters Connect

At this point, it has been talked about for over a year that Boston has a logjam in the outfield. Now, of course, it's better to have a lot of talent, rather than a little bit. When it comes to the Red Sox's outfield, the logjam gives Boston less flexibility, though, especially with Jarren Duran's offensive troubles in 2026.

When everyone was healthy — which was very rare — Boston had an outfield of Roman Anthony, Ceddanne Rafaela, Wilyer Abreu and Duran with one usually in the designated hitter spot. In this scenario, Masataka Yoshida was on the bench usually. Arguably, it's time to rip the Band-Aid off and make a choice here, especially with Eli White under team control through the 2028 season. If the Red Sox make a move, they can ride into the 2027 season feeling comfortable with White as a No. 4 outfielder and not have the same logjam questions. Plus, Boston could then also go out this winter with a focus on adding power to the DH spot.

No. 2 Not Adding More Power

Dec 9, 2024; Dallas, TX, USA; Boston Red Sox chief baseball officer Craig Breslow speaks with the media at the Hilton Anatole during the 2024 MLB Winter Meetings. Mandatory Credit: Jerome Miron-Imagn Images | USA TODAY Sports via Reuters Connect

This one is an easy one. Last offseason, it was talked about how the Red Sox needed more power. That's still the case, although to a lesser extent than a year ago. The Red Sox's trade deadline success positioned them well for the 2027 season with Adley Rutschman and Curtis Mead. But Boston still needs a bit more.

No. 1: Not Extending Adley Rutschman

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

First and foremost, Rutschman is one of the best catchers in the game and is someone you want on your team. He's elite both offensively and defensively. It's why he's a three-time All-Star at just 28 years old. But there's another variable here. Think about how the fanbase reacted when the Red Sox signed Alex Bregman and lost him after a year. He was a star and a fan favorite. Fortunately, Boston only had to give up cash to bring him in, rather than trade chips. Imagine the reaction if Boston let Rutschman walk in a year in free agency after the massive package the Red Sox gave up to get him? It would be a disaster. Now is the time to get a deal done one year before free agency.