Since Roman Anthony emerged as one of baseball's top prospects, the Boston Red Sox have had too many outfielders to fit into the lineup every day. When fully healthy, Boston has Anthony, Ceddanne Rafaela, Jarren Duran, Wilyer Abreu, and Masataka Yoshida to play across the three outfield positions and designated hitter. That’s before factoring in former top prospect Kristian Campbell, who moved to a full-time outfielder in Triple-A Worcester in 2026. 

With Rafaela and Abreu among the premier defenders at their positions, former manager Alex Cora and current manager Chad Tracy were/are left to choose between Yoshida, Duran, and Anthony for the two remaining spots in left field and designated hitter. With Anthony being only 22 years old, it seems unlikely the team wants to move him to a full-time designated hitter role, especially seeing that he profiles as an above-average defender in either corner outfield spot. This left Yoshida and Duran as the main competitors for designated hitter duties. 

Cora was open with the media about the difficulty of navigating the logjam, telling reporters in Cincinnati during the regular-season opening series, “It’s not easy; whoever thinks that this is easy to move them around, they’re wrong. I’m going to say it like that. It’s not that easy, but I’ll make it work.” 

For much of the 2026 season, Tracy didn't have to manage the logjam, as he was without Anthony for 101 games while he worked his way back from a torn ligament in his right ring finger. By the time Anthony had returned on Aug. 30, Yoshida had gone down with a season-ending hamstring strain. 

While injuries are bound to happen throughout the year, there is far too much talent and money invested in the group to have at least one on the bench on any given day, before even factoring in Campbell, who spent the entirety of the first year of his eight-year extension in the minors reworking his swing.  

Will 2026 finally be the offseason when Chief Baseball Officer Craig Breslow makes his manager’s life easier and clears the logjam? 

Boston has spent the last two offseasons trying to move on from Yoshida; however, his defensive limitations and an $18 million average annual value contract have made it impossible to find suitors. While moving on from Yoshida would certainly ease some of the pressure on Tracy and Cora, it would far from solve his problem. Since the team has done all it can to move on from Yoshida, we’ll set him aside for now. 

Breslow’s handling of the logjam is a lesson for other general managers in what not to do when constructing your roster. Since Anthony’s emergence as one of baseball's best prospects, Duran has been the odd man out in the outfield. He is the oldest of the bunch; his best tool is speed, which tends to decline much faster with age, and he plays the same position as Anthony. 

Breslow has at least listened to offers on Duran since his first offseason in 2024, when Duran finished top 10 in MVP voting. However, the team reportedly placed an inordinate price tag on the 29-year-old, valuing him as a perennial MVP candidate rather than the 3-4 WAR player he’s been for most of his career. 

Fast forward to 2026, and Duran has lost almost all the value he once had after posting his worst season, and finishing as one of the worst-qualified hitters in the sport. His down season, paired with an arbitration estimate of $11 million, makes it hard to imagine any team giving up serious assets to acquire him. 

There was plenty about the way Breslow constructed the 2026 roster that raised eyebrows, but the handling of Anthony was among the most puzzling. After failing to replace the star power traded away with Rafael Devers in June 2025, the team expected Anthony to drive the offense in his first full big-league season. Beyond forcing him to be a star in his first big-league season, the team made it almost impossible for Anthony to establish himself by creating chaos in the outfield around him. 

Early in the season, Anthony struggled with his footwork on throws from left field, leading to several errant throws. Rather than letting him work out his problems in game action, the team shifted him to designated hitter, with Duran replacing him in left, keeping him from getting in rhythm offensively and defensively. Typically, teams bring up their top prospects in the best environment they can create. That’s the logic the Red Sox have followed for much of the last decade: calling up top prospects for road debuts, joining clubhouses with veteran leaders and an established culture where they’re not expected to be the savior immediately. 

Everything about Anthony’s arrival flew in the face of that precedent; he was promoted into a clubhouse mired in the drama leading up to the Devers trade, within an already crowded outfield picture, and then soon thrust into a role where he was expected to carry the offense. 

Between injuries and roster construction, Anthony has had a tough start to his big-league career. If he’s going to be seen as THE GUY on offense in 2027, it has to start with a defined defensive role. 

Naturally, Breslow was asked if he felt a decision needed to be made on the outfield at the team's end-of-season press conference. The third-year CBO played things understandably coy. "To be thankful that we have a really talented outfield that has, for a few years now, been at the top of the leaderboards in defense," Breslow said when asked for his assessment of the outfield. "We'll go into the offseason, we'll start to meet on roster construction and see what opportunities exist. But today I don't think there's a decision to be made. I just think about our outfield core as a hallmark of our success," he continued.

Breslow wouldn't say outright that a move is needed to clear the logjam and risk losing any leverage he may have left in trade talks. However, the second part of his answer signals that he understands a decision likely has to come at some point. 

It will be interesting to see how the outfield situation plays out as the offseason progresses. Especially with a lockout looming.