Masataka Yoshida's Rollercoaster Red Sox Tenure May Be End This Winter

Could we have seen the last of Masataka Yoshida in a Boston Red Sox uniform?

Aug 6, 2026; Boston, Massachusetts, USA; Boston Red Sox designated hitter Masataka Yoshida (7) hits a single against the Chicago White Sox in the fourth inning at Fenway Park. Mandatory Credit: David Butler II-Imagn Images | IMAGN IMAGES via Reuters Connect

Before the 2023 Major League Baseball season, the Boston Red Sox went out and made a splash in an attempt to take the lineup — and outfield — to another level.

That splash was signing Masataka Yoshida to a five-year, $90 million deal. At the time, Yoshida was one of the most interesting free agents of the offseason after being posted by the Orix Buffaloes. In 2022, his final season with Orix, Yoshida slashed .336/.449/.559 with a 1.007 OPS, 21 home runs, 89 RBIs and 28 doubles. Unfortunately, that production hasn't carried over to the big leagues. As a rookie, he hit .289 with 15 homers and 72 RBIs, but has had an inconsistent role since and also has dealt with injuries. Now, he has just one more year left on his deal but The Boston Globe's Alex Speier made it sound like his time with the organization will come to an end on the latest episode of the 310 to Left podcast.

“It feels like given the crowd of the 40-man roster and the desire to upgrade, it feels like it’s likelier than not that Yoshida is not back with the Red Sox … You wanna be able to aim higher," Speier said.

Masataka Yoshida's Time In Boston Could End

Aug 15, 2026; Pittsburgh, Pennsylvania, USA; Boston Red Sox designated hitter Masataka Yoshida (7) hits a double against the Pittsburgh Pirates during the third inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | IMAGN IMAGES via Reuters Connect

Yoshida has been floated as a trade candidate over the last few years, but his injuries and contract were simply too big a barrier to get past. Yoshida's deal pays him over $18 million per year. So, last year, he had over $36 million left on his deal, which was a lot. No one was going to take on that type of cash and it would've been a lot for Boston to send in a salary dump. This was especially the case because Yoshida played in just 55 games in 2025.

In 2026, Yoshida played in 87 games and was solid when he was in the lineup, but his season was cut short again. But this year, he has just one year left on his deal. It's more realistic that the Red Sox could find a partner this offseason simply because there is less money left on the deal. Think back to last offseason. The Red Sox dealt Jordan Hicks to the Chicago White Sox in a salary dump. This offseason, it's realistic that the same could happen with Yoshida.

Speier is one of the most plugged-in insiders out there. If he's going to insinuate that Yoshida could be gone, then that's a safe bet. MassLive.com's Chris Cotillo also said that Yoshida "looks like a goner."

If you're a Red Sox fan hoping to see Yoshida play for Boston in 2027, you may end up being disappointed.