Red Sox 2026 Preview: Offseason Moves, Predictions & Championship Hopes (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 for spring training in just a couple of months, it's the perfect time to reflect on the year that was before turning the page to 2026. The Herald's Red Sox reporters, Mac Cerullo and Gabrielle Starr, engage in a lively discussion.

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 - Garrett Crochet's complete-game shutout and the 10-game winning streak before the All-Star break, for instance. But nothing beats Ceddanne Rafaela clinching the first Red Sox postseason berth since '21 with a Friday night walk-off. What about you?

Mac: That was right at the top of my top-10 list from last week, and it's hard to argue it wasn't the season's pinnacle. But personally, being in Toronto for that final road series was truly special. It was my first visit to the city, and exploring Toronto while experiencing a playoff-caliber crowd at the Rogers Centre was unforgettable. However, from a season perspective, the team fell short of its ultimate goal, getting bounced in the first round. So, how do you think this season will be remembered, Gabrielle?

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

Mac: I think this season will be viewed as a prelude to whatever comes next. It was a clear step forward from the forgettable 2022-24 stretch, but no one will hang banners in Boston for a Wild Card appearance leading to an early exit. If 2025 is a blip followed by mediocrity, like 2021, then it won't be remembered much. But if next year signifies the team's true return to form, then this season's team could be like 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?

Gabrielle: I believe they'll add another bat, perhaps Alex Bregman. They also need to manage the balance between Masataka Yoshida, four starting outfielders, Casas (eventually), and Willson Contreras, as they only get one designated hitter spot per game. It's looking crowded.

Mac: I think their next move will reveal a lot about the final roster. 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 goes elsewhere, maybe the next bat will come via trade? I still don't understand how the Red Sox can manage this outfield situation for another year, so until Opening Day, I feel one of them will be moved. With Casas, the Red Sox have time on their side, which is why I'm confident Yoshida will be back. If he's healthy and effective, he can still be a productive DH, and if Casas pushes boundaries, that will be a welcome problem.

Gabrielle: I have no doubt Yoshida can be a productive DH, even if he hasn't hit for power in the last two years. However, the Red Sox don't want him in the outfield, so they can't rotate through the DH spot as easily as other teams. It's made things challenging in the past two seasons, but there's nothing we can do about it. I'd like to see them re-sign Bregman, not only because he's a great fit but also because it means they've finally signed a free agent.

Mac: It's fascinating that Breslow has made 10 trades but hasn't signed a single free agent. Despite not spending in free agency, they've still increased their payroll this offseason. They'll pay Gray $21 million and Contreras $17.25 million, bringing them just below the $244 million Competitive Balance Tax threshold. Adding Bregman would put them over the first threshold and possibly the second, which would be a strong signal to hesitant fans that ownership is committed to winning.

Expectations for 2026

Gabrielle: Let's start broad and zoom in. I think the Red Sox have more starting pitching depth than ever before, but are they currently a better team in other areas and on par with their AL East rivals? I'm not entirely convinced. Toronto and Baltimore have had productive offseasons, especially the Orioles, who got what Boston needed in slugger Pete Alonso. 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 team with these offseason moves? I don't think so.

Mac: As it stands, I think this year's team is comparable to last year's, a playoff contender but not a championship contender. The Rays are likely last place, 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 big difference. Otherwise, the team will rely heavily on Roman Anthony to 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. While he's better equipped than the average rookie star, that's not the point. The Red Sox have been saying they're waiting for him and other young talent to reach the majors, and now they're here. Leadership should be building aggressively to support them.

Mac: Pitching-wise, I think the Red Sox are in great shape. Crochet is undoubtedly a force, 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 effective as MLB starters. 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 too, but there are more question marks, and the team needs to add a veteran left-handed arm or two. Going into spring training with Jovani Moran and Tyler Samaniego as the only non-closer lefty relievers on the 40-man roster seems risky.

Gabrielle: I agree, especially regarding Gray. But they'll need to do whatever it takes to keep Crochet healthy, as the depth he brings is unparalleled. The parallels with Chris Sale have been eerily accurate, both leading the majors in strikeouts and either MLB or the AL in innings in their first Red Sox seasons, and finishing as Cy Young Award runners-up to an AL Central pitcher. From here on, though, 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 try to predict how it will end. The '25 Red Sox were 89-73, third in the AL East, and lost the Wild Card round 2-1 to the Yankees. I predict 91-71 and third in the division again in '26, second if Anthony has the season we expect. But they'll make it to the ALDS before losing in five games. What do you think, Mac?

Mac: With the caveat that the offseason isn't over and we don't know the exact roster, I think this year's team will take another step and win the AL East. The Red Sox weren't far behind the Blue Jays or Yankees last year, and their pitching is still 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 regarding defense and 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 Preview: Offseason Moves, Predictions & Championship Hopes (2026)
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