Red Sox $90M Masataka Yoshida Dilemma Getting More Complicated

The Boston Red Sox brought Masataka Yoshida into the organization ahead of the 2023 season on a five-year, $90 million deal.

At the time, the expectation was that Yoshida was going to be someone who came in and hit at the top of the order and helped in the outfield. Now, after three seasons in the organization, his standing with the team is murky, to say the least.

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Yoshida is currently a man without a role. The Red Sox have four outfielders ahead of him in Roman Anthony, Jarren Duran, Ceddanne Rafaela and Wilyer Abreu. With the four outfielders on the roster, the current expectation is that one will also occupy the designated hitter spot. So, Yoshida doesn't have a clear pathway in the outfield or DH with the roster as currently constructed.

One obviously was to proceed would be to survey the trade market to see if there is something out there. MassLive.com's Chris Cotillo reported there has been "tangible" interest in Yoshida.

The Red Sox have a tough decision on their hands

Sep 30, 2025; Bronx, New York, USA; Boston Red Sox outfielder Masataka Yoshida (7) hits a two run RBI 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

"According to sources with knowledge of the Red Sox’ thinking, there has been tangible trade interest in Yoshida throughout the winter, with teams recognizing his offensive upside (and the opportunity cost) in discussing him with Boston," Cotillo wrote. "Still, considering Yoshida’s limits in 2025 (he got just 205 regular season plate appearances after returning from the injured list) coming off labrum surgery, the Sox might have to wait to make a move. Two sources cautioned that teams who might want to deal for Yoshida likely want to see how he does in spring training games before increasing their aggressiveness.

"It’s unclear what the Red Sox could get back in such a deal, which would be a salary dump similar to the January trade that sent Jordan Hicks and pitching prospect David Sandlin to the White Sox. The Red Sox did not have a path to attach some of Yoshida’s deal to Sandlin in talks with Chicago, sources said, because he was not a fit for the White Sox’ roster. Over the weekend, a rival evaluator painted a less-than-rosy picture of Yoshida’s trade value."

Cotillo cited an anonymous evaluator and the potential return isn't what you'd think, though.

“It’s pretty low across the industry,” the evaluator opined. “A lot of teams are really down on the defense and power being below average. Boston would have to pay a very large chunk of salary or part with a top-five prospect to get teams interested.”

Yoshida has two seasons left on his deal and will make just north of $18 million each season. Trading an above-average bat plus a "very large chunk" of the remaining salary wouldn't be ideal. It would be even worse to include a top-five prospect for him in a deal. All in all, there is no easy path forward.

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