Red Sox 2026 Season Outlook | Key Offseason Moves & Predictions (2026)

Red Sox Point-Counterpoint: A Way-Too-Early Look Ahead to the 2026 Campaign

As we approach the final days of 2025, the baseball world is gearing up for the upcoming season, with pitchers and catchers set to report to spring training in just a couple of months. It's the perfect time to reflect on the year that was before we turn the page to 2026.

The Herald's Red Sox reporters, Mac Cerullo and Gabrielle Starr, engage in a lively discussion, sharing their thoughts and insights.

Favorite Moment of 2025

Mac Cerullo: Happy New Year, Gabrielle! It's mind-boggling how another Red Sox season has come and gone. Before we dive into the future, what was your favorite moment from this past year?

Gabrielle Starr: Happy New Year, Mac! There were so many highlights, like Garrett Crochet's complete-game shutout and the 10-game winning streak before the All-Star break. But nothing beats Ceddanne Rafaela securing the first Red Sox postseason berth since '21 with a Friday night walk-off. What about you?

Mac: That was my number one pick from last week's top-10 list, and it's hard to argue with that as the season's pinnacle. However, from a personal perspective, attending the final road series in Toronto was truly special. It was my first visit to the city, and exploring Toronto while experiencing a playoff-atmosphere Rogers Centre crowd made it an unforgettable memory. As for the season, the team fell short of its ultimate goal, exiting in the first round. How do you envision this season being remembered in hindsight?

Gabrielle: Chaotically! That's how I see it being remembered. From the Rafael Devers drama and trade to Triston Casas and Tanner Houck injuries, and Garrett Crochet's stellar debut, to the Fenway Greens' walk-offs, and their brief postseason run, this season was one of the most chaotic Red Sox campaigns in my memory. We've used the term 'roller coaster' before, but it's especially fitting for 2025. What's your take?

Mac: I believe this season will be viewed as a prelude to what's to come. It was a significant step forward from the forgettable 2022-2024 stretch, but a Wild Card appearance leading to a first-round exit isn't enough to hang banners in Boston. If 2025 is a blip followed by mediocrity, like 2021, it might be overlooked. However, if next year signifies the team's true return to form, then last season's squad could be akin to the 2015 Cubs, who weren't quite ready but showed immense potential.

Remaining Offseason To-Do List

Mac: Even though we're about to turn the page to 2026, the offseason isn't over yet. What do you think the Red Sox will do to strengthen their roster in the coming weeks?

Gabrielle: They'll likely add another bat, perhaps Alex Bregman. They also need to manage the crowded outfield situation, balancing Masataka Yoshida, Triston Casas, Willson Contreras, and four starting outfielders, as they can only have one designated hitter per game.

Mac: Their next move will reveal a lot about the final roster composition. If Bregman re-signs, they'll have a complete lineup, and it'll be up to Craig Breslow and Alex Cora to piece it together. But if Bregman signs elsewhere, a trade for another bat might be in the cards. I still don't see how the Red Sox can manage this outfield situation for another year, so we'll likely see one of them traded by Opening Day. With Casas, the Red Sox have time on their side, which is why I'm confident Yoshida will return. If he's healthy and productive, he can still be a valuable DH, and if Casas starts pushing boundaries, it will be a welcome challenge.

Gabrielle: Yoshida can be a productive DH, despite his lack of power in recent years. However, the Red Sox's reluctance to play him in the outfield limits their ability to rotate the DH spot, which has been challenging in the last two seasons. I'd love to see them re-sign Bregman, not only because of his fit but also because it would mark the first time they've signed a free agent.

Mac: It's astonishing that Breslow has made 10 trades but hasn't signed a single free agent. Interestingly, despite their lack of free-agent spending, they've increased their payroll this offseason, paying Gray $21 million and Contreras $17.25 million, bringing them just below the $244 million Competitive Balance Tax threshold. Adding Bregman would push them over the first threshold and possibly the second, signaling to hesitant fans that ownership is fully committed to winning.

Expectations for 2026

Gabrielle: Let's start broad and narrow in. The Red Sox have more starting pitching depth than ever, but are they better in other areas and on par with their AL East rivals? I'm not entirely convinced. Toronto and Baltimore have had productive offseasons, with the Orioles acquiring Pete Alonso, a significant boost for Boston. The Red Sox could be a Wild Card team again, and maybe they'll even advance past the first round. But has Breslow built a World Series contender with these moves? I don't think so.

Mac: As currently constructed, I believe this year's team is comparable to last year's, a playoff contender but not a championship favorite. The Rays are likely a last-place team, but the Orioles have made significant strides, and the Blue Jays and Yankees should be strong again. If the Red Sox add another bat and perhaps a reliever or two, it will make a substantial difference. Otherwise, the team will rely heavily on Roman Anthony's transition from a promising rookie to a legitimate star.

Gabrielle: I agree, and that's the issue: not enough done to improve the offense, and too much pressure on Anthony. He's better equipped than the average rookie star, but that's not the point. The Red Sox have been patient, waiting for Anthony and other young talent to reach the majors, and now it's time to build aggressively around them.

Mac: Pitching-wise, the Red Sox are in a great position. Crochet is an exceptional talent, and I'm higher on Sonny Gray than most. Brayan Bello may have another level to reach, and Patrick Sandoval and Kutter Crawford have proven their effectiveness in the MLB. With these guys and less experienced options like Johan Oviedo, Connelly Early, and Payton Tolle, the Red Sox should have one of the best rotations in MLB. The bullpen could be elite, but there are question marks, and the team needs to add a veteran left-handed arm or two. Starting spring training with Jovani Moran and Tyler Samaniego as the only non-closer lefty relievers on the 40-man roster seems risky.

Gabrielle: Agreed, especially regarding Gray. However, they must prioritize keeping Crochet healthy, as his depth is unparalleled. The parallels between Crochet and Chris Sale have been uncanny, both leading the majors in strikeouts and either MLB or the AL in innings in their first Red Sox seasons, and both finishing as Cy Young Award runners-up to an AL Central pitcher. From now on, I want Crochet's Red Sox tenure to mirror Sale's only through a World Series championship.

Too-Early Predictions

Gabrielle: We're at the beginning of '26, but let's predict its end. The '25 Red Sox finished 89-73, third in the AL East, and lost the Wild Card round 2-1 to the Yankees. I predict 91-71 and a third-place finish in the division again in '26, but second if Anthony has the season we expect. They'll make it to the ALDS but lose in five games.

Mac: With the caveat that the offseason isn't over and team compositions are uncertain, I believe this year's team will take another step forward and win the AL East. The Red Sox weren't far behind the Blue Jays or Yankees last year, and their pitching is better than the Orioles'. The Blue Jays may have peaked and could lose Bo Bichette in free agency, and the Yankees have their own questions, especially defensively and in the bullpen. I predict the Red Sox will finish 93-69 in a highly competitive division and lose in six games to the Mariners in the ALCS.

Red Sox 2026 Season Outlook | Key Offseason Moves & Predictions (2026)
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