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Red Sox Insider Predicts How Masataka Yoshida 'Problem' Will Be Handled

Will this logjam work itself out without the Red Sox forcing a move?
Sep 28, 2025; Boston, Massachusetts, USA; Boston Red Sox designated hitter Masataka Yoshida (7) hits a home run against the Detroit Tigers in the first inning at Fenway Park. Mandatory Credit: David Butler II-Imagn Images
Sep 28, 2025; Boston, Massachusetts, USA; Boston Red Sox designated hitter Masataka Yoshida (7) hits a home run against the Detroit Tigers in the first inning at Fenway Park. Mandatory Credit: David Butler II-Imagn Images | David Butler II-Imagn Images

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Things are shaping up for Masataka Yoshida to become perhaps the highest-paid bench player in Major League Baseball this year.

With two years remaining on the five-year deal he signed to come to Boston, valued at just over $37 million, Yoshida has proven that he's at least an above-average major league hitter. But the Red Sox don't trust that he can handle the outfield, and after his name has been thrown around in trade talks for the last year-plus, the 32-year-old has to feel like he's in a precarious position.

Still, the fact that the Red Sox haven't traded Yoshida yet, combined with manager Alex Cora consistently promising that everyone on the roster can get the at-bats they need, has made the prospect of a trade seem less likely than some may have predicted.

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Is Yoshida going to survive trade rumors again?

Yoshida
Sep 28, 2025; Boston, Massachusetts, USA; Boston Red Sox designated hitter Masataka Yoshida (7) hits a home run against the Detroit Tigers in the first inning at Fenway Park. Mandatory Credit: David Butler II-Imagn Images | David Butler II-Imagn Images

With under two weeks to go before opening day, one Red Sox insider -- Chris Cotillo of MassLive -- gave his two cents on how he thought the Red Sox would handle Yoshida's contract with the team moving forward.

"It is a good problem to have, but it's a problem nonetheless," Cotillo said during an appearance on the "Monster Territory" podcast. "It just comes down to, can they get a reasonable trade offer? I think if they do, they'd be willing to pull the trigger and move on from him.

"If not, there are worse things in the world than rolling out a 26-man Opening Day roster with this guy who's a proven big leaguer as your fourth, fifth outfielder and a bench bat."

Reading between the lines, it would seem that to this point, the league has been collectively unwilling to swallow enough of Yoshida's deal to placate the Red Sox. And if he comes out of the gates on fire this season, there's no guarantee that the Red Sox will still be just as willing to move on from him as they perhaps previously were.

When someone is involved in trade smoke for this long, you can never be truly surprised if they eventually get moved. But the fact that it hasn't happened to Yoshida yet also makes it feel increasingly unlikely that it eventually will. Cotillo's comments reinforced that notion.

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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@moreviewsmedia.com