The Boston Red Sox appear to be navigating a tricky roster puzzle as they look ahead to the upcoming season, and one name that keeps surfacing in trade chatter is Masataka Yoshida. While the team has reportedly kicked the tires on some big bats - think Pete Alonso, Kyle Schwarber, and Eugenio Suárez - none of those talks materialized into offers, and for good reason: the designated hitter spot in Boston is already a bit of a logjam.
Kyle Schwarber is locked in as a full-time DH. Suárez, at this stage of his career, probably should be.
Alonso may not be there yet, but he's trending in that direction. And with Willson Contreras expected to split time between first base and DH, plus Masataka Yoshida still looking for a role, the Red Sox are running out of real estate in the lineup.
The organization values flexibility at the DH spot - they want to be able to play matchups and rotate players in and out depending on who’s on the mound. That becomes harder when you have too many players who are best suited for that role. Yoshida’s streaky bat, limited defensive value, and lack of speed have made him a tough piece to fit into that puzzle - and even tougher to move on the trade market.
If the Red Sox are serious about parting ways with Yoshida, they’ve already shown the blueprint in the recent Jordan Hicks deal with the White Sox. That trade was a classic salary dump: Boston packaged Hicks with right-handed pitching prospect David Sandlin - previously ranked as their No. 8 prospect - and sent $8 million to Chicago to help cover Hicks’ $24 million salary over the next two seasons. In return, they got back Gage Ziehl, a former Yankees prospect.
It wasn’t a flashy deal, but it got the job done. And it might be the kind of move Boston has to replicate if they want to move Yoshida.
Yoshida is still owed $36 million over the next two years, and for a player who’s likely to be a full-time DH on most rosters, that’s a hefty price tag. To convince another club to take that on, Boston may need to sweeten the pot - and that could mean parting with a high-upside prospect like Mikey Romero or Justin Gonzales. That’s the cost of doing business when you’re trying to clean up a roster fit that just hasn’t worked out.
It’s worth noting that Boston reportedly tried to send Yoshida to Seattle not long ago, but those talks didn’t go anywhere. The difference now? Fewer years left on the contract - and a clearer picture of how Yoshida fits (or doesn’t) in the Red Sox’s plans.
To be clear, this wouldn’t be a pure salary dump. Yoshida can still hit.
He’s got a good eye, solid contact skills, and the potential to be a high-average bat in the right environment. But on this Red Sox roster, with so many mouths to feed at DH and first base, he’s become more of a redundancy than a necessity.
That’s where the Hicks deal becomes instructive. It showed the front office is willing to take a hit, package a prospect, and move on from a contract that no longer makes sense. It wasn’t comfortable, but it was calculated - and it may be the only path forward if the Red Sox want to free up space and get back to building a more balanced, flexible lineup.
At the end of the day, Yoshida’s future may depend less on his talent and more on timing, fit, and how much Boston is willing to pay - both in dollars and in prospect capital - to make a deal happen.