The Boston Red Sox were expected to have a busy offseason to build on their short 2025 playoff appearance, their first in four seasons. Boston delivered, albeit not in the way many reporters and fans expected — Alex Bregman left and no one was traded from the outfield surplus.

Roster construction questions have loomed over the Red Sox since last season. They were emphasized by Masataka Yoshida’s return from surgery rehab and Roman Anthony’s arrival to the big leagues. Boston has four-six outfielders, depending where it envisions Yoshida and Kristian Campbell playing, and a designated hitter spot it likes to keep flexible — moving an outfielder makes the most sense to solve this quandary.

The best case-scenario for addressing the packed outfield would be to find a trade suitor for Yoshida, which has proven difficult-to-impossible over his first three seasons with the Red Sox. Red Sox insiders Chris Cotillo and Sean McAdam of MassLive think Boston may have to make an extremely difficult decision to free up Yoshida’s roster spot.

“You wonder, at what point does this become a — not Patrick Sandoval situation — but a Pablo Sandoval, where you rip the Band-Aid off and just release,” McAdam theorized on the “Fenway Rundown” podcast (subscription required).

Red Sox insiders wonder if/when Boston will release Masataka Yoshida, as it did with Pablo Sandoval in 2017

Pablo Sandoval is infamous among Red Sox fans. He signed a five-year, $90 million deal before the 2015 season and he only lasted two and a half years before the Red Sox cut him loose. His tenure was marked by career lows at the plate, injuries and a perceived lack of effort that soured things quickly with Boston. Yoshida hasn’t lived up to the expectations the Red Sox had when they signed him, but he’s no Sandoval.

McAdam postulated that the Red Sox may be waiting until there is less money remaining on Yoshida’s contract before they potentially release him. Like Sandoval, Yoshida signed a five-year, $90 million deal before the 2023 season, which has only just reached its halfway point. The Red Sox still owe him over $36 million, and by releasing him, they’d be forced to eat that money.

The amount of money remaining on Yoshida’s contract is just one obstacle that may be preventing the Red Sox from finding a trade partner to move him elsewhere. Yoshida has never played more than 140 games in a MLB season with 303 total over his three-year tenure, mostly because he’s dealt with so many injuries since moving stateside.

Maybe the Red Sox could attach a top prospect to him and eat some of his contract money to entice another team into a trade, like they already did with Jordan Hicks this winter. But that would require sacrificing a quality prospect and it would cost more money, just to move a good hitter who tries hard at his job.

There’s no easy way to fit Yoshida onto Boston’s roster, but the decision to salary dump or release him will be just as hard. Yoshida hasn’t been a bad player for the Red Sox and he doesn’t deserve the Sandoval treatment, but his trade value may only decrease if he spends another year with minimal playing time. Alex Cora and Craig Breslow have a real dilemma on their hands with this roster.