2 trade partners for Red Sox, Masataka Yoshida in a Jordan Hicks-style salary dump

Could now be the time?
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
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

Masataka Yoshida has been a thorn in the side of Boston Red Sox fans for two years. After signing a five-year, $90 million contract before the 2022 season, the lefty hasn't lived up to the expectations of the contract and has compounded roster and (self-imposed) financial problems.

The Japanese DH hasn’t been bad by any means. He owns a career .282 batting average with a .762 OPS and has been worth 3.0 bWAR. Still, that level of production hasn’t quite justified an $18 million annual salary — especially since he’s mostly a full-time DH, which further limits his overall value.

His lack of fielding ability and large contract would mean the Sox would need to send money to whichever team acquired him, just like in the Hicks deal. Not many teams would look to take on his services, which is why he's still on the Sox. With only two years left on the deal, now may be the time a team could take a chance on him.

2 trade partners for Red Sox, Masataka Yoshida in a Jordan Hicks-style salary dump

Rockies

For Yoshida to be successful, finding him regular at-bats will be key. Colorado can certainly offer that. In their constant state of rebuilding, the Rockies could take a chance to add a veteran hitter to their lineup to make them a little bit more competitive. Adding a prospect as a sweetener could aid their rebuild, too.

Yoshida may play well in Coors as well. With balls traveling better out there, his contact style could help him place them in the gaps more. It really would be a low-risk move for a team that is just looking to be more competitive next season. If he is playing really well, they could flip him at the deadline, too.

Twins

Minnesota is a completely different situation. While the Tigers are the class of the AL Central, the Twins still have enough good players to potentially make a wildcard push. The one position they are truly lacking in right now is DH. According to Fangraphs Roster Resource, longtime backup catcher Victor Caratini is currently projected as the Opening Day DH. The change in leadership at the top of the Twins organization may help the teams get a trade across the line after they struggled at the deadline.

Yoshida would be a major upgrade for them. The lefty could easily get regular at-bats there and lengthen a solid lineup. In the past, Minnesota has not been scared of a high payroll, and even with Boston eating money, they shouldn't have any problem adding whatever portion of the contract they take on, either.

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