Three questions facing the Red Sox this offseason

In some ways, the 2025 season was a success for the Boston Red Sox.

The fact that the Red Sox made the playoffs at all was a bit of a surprise given a deal made in June. Third baseman Rafael Devers was viewed as a cornerstone player until his discontent led the Red Sox to send him to San Francisco. That move lit a fire under the then 37-36 Red Sox as they fought their way into the postseason for the first time since 2021.

The Red Sox return to the playoffs proved to be brief as they were eliminated during the Wild Card round. To add insult to injury, the Yankees beat the Red Sox in three games. The Red Sox now face an interesting offseason as they look to take the next step toward a World Series.

Three questions for the Boston Red Sox heading into the offseason

1. Will third baseman Alex Bregman return?

The Red Sox made a splash in the free agent market just before spring training when they signed Bregman to a three-year, $120M contract. That contract also included an opt-out clause after each season, which Jon Heyman of the New York Post reported Bregman will exercise to re-enter the market.

Although Bregman missed several weeks due to a strained right quad, he put together an impressive season with the Red Sox. Bregman posted a .273/.360/.462 batting line over 495 plate appearances, hitting 18 homers and 28 doubles. His defense at third made a significant difference for a pitching staff that had the fifth-highest ground ball rate in the majors. Bregman is going to be expensive but the Red Sox need to bring him back.

2. Is this the offseason the Red Sox trade outfielder Jarren Duran?

The Red Sox have a logjam in the outfield. Duran, Roman Anthony, Wilyer Abreu and Ceddanne Rafaela have established themselves as everyday players but are vying for three outfield spots. While Rafaela is capable of playing around the infield, he is a stellar defensive center fielder, ranking fifth in the AL with nine runs saved. Meanwhile, the designated hitter spot is taken up by Masataka Yoshida, who should never see time in the outfield. Another issue is that Anthony, Abreu and Duran are left-handed hitters, leaving the lineup unbalanced.

Trade rumors have swirled around Duran in particular, with Sean McAdam from MassLive.com reporting in July that the outfielder could be moved this offseason. Although the San Diego Padres have been attempting to acquire Duran since last offseason, the Red Sox will likely have plenty of suitors should he be placed on the trade block. 

3. Can the Red Sox find a second top-of-the-rotation starter to pair with Garrett Crochet?

The Red Sox rotation after Crochet was more solid than anything else. Brayan Bello took a significant step forward and appears ready to settle in as a middle-of-the-rotation arm. Prospect Peyton Tolle showed flashes of promise and should be in the mix for a spot on the Opening Day roster. However, Lucas Giolito has a mutual option for 2026, something rarely picked up on both sides. Even if Giolito returns, he is best suited with Bello as a third or fourth starter.

The lack of a viable second option was a factor in the Red Sox early departure from the playoffs. Crochet did his part in Game 1 but the Red Sox did not have the rotation depth needed to advance. Although the likes of Framber Valdez, Dylan Cease and Michael King will be expensive in free agency, the Red Sox may need to sign one of those pitchers to take the next step.