$90 Million Red Sox Outfielder Considered Nightmare of Contract, Despite Playoff Showing

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Boston Red Sox Chief Baseball Officer Craig Breslow

The offseason is finally here for the Boston Red Sox, a challenging time for the organization. Not only did the Red Sox not accomplish what they were looking to throughout the 2025 campaign, falling in the Wild Card round to the New York Yankees, but they also have some questions about their long-term future.

On paper, the Red Sox seem to be pretty well off, but they’ll have to make decisions on what they want to do with the outfield, more importantly than anything else. With Jarren Duran, Masataka Yoshida, Roman Anthony, when healthy, and others, there’s certainly a logjam in the outfield.

For some, that’s a reason to move on from somebody like Yoshida, while others argue that his contract is the bigger problem. The contract situation was one that Kerry Miller of Bleacher Report pointed out, listing him as the one contract from the Red Sox that will be a nightmare by 2027.

“With four young, talented outfielders each under team control through at least 2028, Boston may well be looking to unload an expendable Yoshida this offseason. And if that’s the plan, at least he hit .333 in September before also going 4-for-7 at the dish in the wild card round loss to the Yankees.

“Might be able to find a taker for the two years and more than $37 million left on his deal,” Miller wrote .

Should the Red Sox Move on Masataka Yoshida?

If the Boston Red Sox decide to move on from Yoshida, it could allow some of their other players to play.

However, with an obvious need to get better on the mound and add maybe one more bat, especially at first base, if things go as well as they possibly can in the offseason for this organization, they might have to move on from a few prospects along the way. That could mean that Yoshida has a chance to play daily next year, as Jacob Levine of FanSided believes that with how well he played in the postseason, it seems like he’s staying put.

“With Jarren Duran hopefully departing this winter, this will still leave the team with Wilyer Abreu, Roman Anthony, Ceddanne Rafaela, and Masataka Yoshida as well. With how hot Yoshida was this postseason, it seems very well that he’ll be staying put,” he wrote .

Is the Red Sox’s Outfield Depth a Good Problem?

There haven’t been any reports suggesting that the Boston Red Sox will move on from Yoshida, but things can change. When examining the situation, Tom Carroll of WEEI reported that Craig Breslow believes the Red Sox’s outfield situation is an advantage, not an issue.

“I would argue that having 4 outfielders capable of taking 550 at bats is a great place to be, and I have a ton of confidence in Alex [Cora’s] ability to manage the people and the personalities…”

Considering Breslow will be the one making most of the decisions that have to be made this winter, it seems very likely as of now that none of them are on the trade block. However, if they can get out of Yoshida’s deal due to some of his injuries, it might not be a bad idea to consider.

Jon Conahan covers the NBA and NFL for Heavy.com. Since 2019, his sports coverage has appeared at Sports Illustrated, oddschecker, ClutchPoints and Sportskeeda. More about Jon Conahan