Masataka Yoshida is saving the Boston Red Sox’s season, but he’s simultaneously creating a conundrum for the front office this winter.

Yoshida looked well and truly cooked at the end of August. He had a .609 OPS in 35 games on the season, with exactly one home run that didn’t come against a position player. But starting on Sept. 2, everything started to change.

In 20 games in September, Yoshida batted .333 with an .817 OPS. Boston legitimately might not have made the playoffs without him, and then on Tuesday, he provided the game-winning two-run single on the first pitch he ever saw in postseason play.

Masataka Yoshida

Sep 30, 2025; Bronx, New York, USA; Boston Red Sox outfielder Masataka Yoshida (7) hits a two run single during the seventh inning against the New York Yankees during game one of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images / Brad Penner-Imagn Images

Right now, Yoshida is indispensable for the Red Sox. If there’s a righty on the mound, there may not be a single hitter manager Alex Cora would rather have in the batter’s box. Cora couldn’t wait to deploy him on Tuesday night against reliever Luke Weaver, and he rewarded the skipper with a laser up the middle.

No one believes Yoshida is a bad major league hitter, full stop, but the fact that he gets paid $18 million a year (on a five-year contract) to be a platoon designated hitter, and one without much home run power, naturally creates a lot of questions about his long-term fit in Boston.

In fact, it’s often been speculated that this offseason could be the opportunity the Red Sox need to finally cut bait with Yoshida. That could mean a trade, or even the Red Sox designating him for assignment to get him off the roster and create more lineup flexibility.

We’ve seen, though, that in every year he’s been in Boston, Yoshida has a month-long stretch where he completely carries the offense. And this year, it’s come at a time when no one else was carrying their weight offensively. Is that trait more valuable than the advanced stats would indicate?

Depending on how he finishes out this playoff run, Yoshida might make the Red Sox look reckless for that decision, regardless of whether or not it’s best for the sake of roster harmony over the next couple of seasons.

Chief baseball officer Craig Breslow is quickly developing a reputation for making the hard, cold-blooded decisions. But even if he’s ready and willing to get rid of Yoshida, can he be sure that’s the right move to make?

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