Masataka Yoshida Gets Ominous 'Bold Prediction' From Red Sox Insider

How does this season end for the 32-year-old?

Feb 17, 2026; Lee County, FL, USA; Boston Red Sox left fielder Masataka Yoshida (7) poses for a photo during media day at JetBlue Park. Mandatory Credit: Kim Klement Neitzel-Imagn Images | Kim Klement Neitzel-Imagn Images

If there's any offseason storyline lingering over the Boston Red Sox as games begin, it's the awkward roster fit of Masataka Yoshida.

At this point, we can acknowledge that the Red Sox would have liked to trade Yoshida over the last year or so. They just haven't been able to find a team willing to eat the $37 million he's owed over the next two seasons, or any substantial chunk of that amount that would satisfy Boston.

But as Yoshida enters this season as the fifth outfielder and extra designated hitter on this Red Sox roster, one team insider believes something has to give relatively soon.

If you like our content, choose Sports Illustrated as a preferred source on Google.

Will Red Sox trade Yoshida during 2026 season?

Oct 2, 2025; Bronx, New York, USA; Boston Red Sox outfielder Masataka Yoshida (7) hits a single in the fourth inning against the New York Yankees during game three of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | Vincent Carchietta-Imagn Images

On Thursday, Jen McCaffrey of The Athletic made three bold predictions for the Red Sox's season, one of which was that Yoshida would be traded away by the end of July.

"All offseason, the Red Sox said they would find a way to make their four-man outfield plus Yoshida work by rotating players at designated hitter. We’re about to find out how well they can accomplish that," wrote McCaffrey.

"The Red Sox have long tried to find a trade partner for Yoshida, but given that the 32-year-old is owed $18.5 million each of the next two years, finding a fit has been tough. By the summer, they will either take on most of his salary or include a prospect in a deal for Yoshida to even out their already crowded DH/outfield picture."

Not to get too colloquial, but no Red Sox fan who "knows ball" dislikes Yoshida. He's a good hitter, sometimes even the best on the team when he's going right. He's also played through injuries over the last three seasons that have zapped some of his power.

That doesn't mean it's unwise to trade him if the Red Sox see a fit, however. Chief baseball officer Craig Breslow is a man who plays the value game, perhaps to a fault, and if the value dictates that it's time to clear up the logjam, it's probably the right move for this Boston lineup.