Key Points
Bullet point summary by AI
- The Boston Red Sox enter 2026 with a deep, balanced roster but face potential midseason roster shifts.
- Certain veterans, including a Jarren Duran, could be moved before the trade deadline to optimize the team.
- These moves could dramatically alter the team's playoff chances and reshape the American League landscape.
Fresh off their first postseason appearance since 2021, the Boston Red Sox have a roster built to contend for an American League East title — though, as is always the case, we’re sure the clubhouse will look far different on August 1 than it did on Opening Day.
Despite losing All-Star third baseman Alex Bregman to the Cubs, the Red Sox have arguably a better roster than they did last year. Veteran pitchers Sonny Gray and Ranger Suárez join Garrett Crochet in the rotation, and first baseman Willson Contreras arrives as a middle-of-the-order bat. If all goes to plan, we’ll get a full year out of top prospects Marcelo Mayer and Roman Anthony, and Gold Glove-winning center fielder Ceddanne Rafaela might be on the verge of superstardom.
However, don’t be surprised if the Red Sox move on from some notable veterans within the coming months. Lead baseball executive Craig Breslow continues remaking the roster in his image, and there are a few players who, simply put, might not fit what he has in mind moving forward.
Honorable mention: Sonny Gray, P
What to know: For what it’s worth, I have high expectations for the Red Sox, and I truly think they’re capable of a deep playoff run. With that said, there’s always at least one or two teams that significantly disappoint every year, so it’s theoretically possible the 2026 Red Sox could fall into that category.
If, and this is a big if, the Red Sox are out of the playoff picture in July, then there is no reason for them to keep Gray through season’s end. The three-time All-Star turns 37 in November and has a 2027 team option.
Which team should trade for him? It definitely won’t be the Yankees, not only because the two are division rivals but because Gray has outright said he didn’t enjoy pitching for the Bombers. Even if the Yankees are betting favorites to win the American League near the end of July, it’s hard to envision Gray donning the pinstripes again.
Assuming that they’re in the playoff hunt, the Royals should definitely consider adding Gray as a rental. He’s familiar with the AL Central, having previously pitched for the Twins, and the Royals’ rotation could benefit from an added veteran arm.
Garrett Whitlock, P
What to know: Whitlock’s inclusion might surprise some, especially after he dazzled with a 2.25 ERA and a 91-24 K-BB ratio over 72 innings last year. Boston wisely made Whitlock a full-time reliever for the first time since 2021, and he played a pivotal role in helping the Red Sox return to the playoffs.
However, Whitlock turns 30 in June, and he has two team options left on his contract. Depending on how Boston’s pitching staff looks, I wouldn’t be shocked to see Breslow pull the “flip a player while their value is high” move.
Which team should trade for him? For the sake of conversation, let’s assume that a team would acquire Whitlock intending to keep him in the bullpen, at least for the remainder of 2026. The Cubs could definitely use another impact reliever, even more so if closer Daniel Palencia regresses. The same goes for the Tigers, though I wouldn’t blame Breslow if he’d prefer to keep Whitlock out of the American League.
Jarren Duran, OF
What to know: Duran has emerged as one of my personal favorite players, and he’s seemingly been the topic of trade rumors for nearly a year now. Nothing is forever — just look at how the Red Sox addressed the Rafael Devers situation — and Boston’s outfield logjam means Duran is expected to be the everyday DH.
Even if Boston holds a playoff spot near or at the trade deadline, would anyone truly be surprised to see the Red Sox part ways with Duran? Remember, Breslow inherited Duran, so there may not be an emotional attachment between the two that Breslow could have with the players he brought in.
Which team should trade for him? I’d like to see the Braves make a play for Duran, especially after left fielder Jurickson Profar’s season-ending PED suspension. Atlanta should be back in the playoff hunt this summer after a disappointing 2025 season, and Duran makes too much sense for the Braves’ loaded lineup.
Masataka Yoshida, DH/OF
What to know: Yoshida will be a free agent after next season, and he appears slated for a rotational outfield and designated role. Realistically, the Red Sox should have seriously looked into trading Yoshida this offseason, considering how many outfielders the big-league roster has right now. Paying a designated hitter $18 million to come off the bench and start maybe once or twice a week is never ideal, regardless of their pedigree or track record, neither of which Yoshida has since arriving stateside in 2023.
Which team should trade for him? Of all the players we’ve discussed, Yoshida is the hardest one to find a new team for, primarily because injuries could force some clubs to move someone to DH. Let’s use the Mets as an example. If Juan Soto hurts his shoulder or elbow and the Mets feel he can hit but he’d be limited in the outfield, then it’s reasonable to assume they’d simply make him the everyday DH.
It’s a copout, but I’m going to leave this one blank. Let’s see where teams are in June or early July and whether they believe that Yoshida would be an upgrade at DH, or if they’re better off sticking with their current roster.