TORONTO, ON – SEPTEMBER 23: Masataka Yoshida #7 of the Boston Red Sox looks on from the dugout during a game against the Toronto Blue Jays on September 23, 2025 at Rogers Centre in Toronto, Ontario. (Photo by Maddie Malhotra/Boston Red Sox/Getty Images)

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Peter Chawaga

By Peter Chawaga

Contributing Sports Writer

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Despite a second-half surge in the regular season to earn a playoff berth, the Boston Red Sox seem to have a lot of work to do this winter.

If they hope to compete with the likes of the New York Yankees and Toronto Blue Jays for the top of the American League East division, the Red Sox will have to reshape their infield as Alex Bregman plans to opt out, consider bringing in a frontline starter to pair with Garrett Crochet and potentially address a hole at first base with a new addition.

As the Red Sox move forward this offseason, they could also revisit the role of designated hitter Masataka Yoshida, who has missed considerable time with injuries since signing a $90 million deal with the team.

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TORONTO, ON - SEPTEMBER 23: Masataka Yoshida #7 of the Boston Red Sox looks on from the dugout during a game against the Toronto Blue Jays on September 23, 2025 at Rogers Centre in Toronto, Ontario. (Photo by Maddie Malhotra/Boston Red Sox/Getty Images)

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“At DH, Yoshida’s albatross contract isn’t getting any more manageable,” Chris Cotillo wrote for MassLive. “The third-year player heated up late but still posted just a .696 OPS in 55 games for $18 million this year. He’s under control for two more seasons but is overpaid, and the Red Sox know it.”

Ultimately, Cotillo believes the Red Sox will cut ties with Yoshida, and that could pave the way for the team to bring in Philadelphia Phillies superstar slugger Kyle Schwarber, who is headed toward free agency.

“The prediction here is that … (Craig) Breslow spends big on a big bat at DH, with Schwarber as the top candidate,” Cotillo wrote. “Yoshida is playing elsewhere on Opening Day.”

With two more years at $18.6 million each ahead for Yoshida, the Red Sox might have a hard time finding a trade destination for him. But if they are willing to eat some salary to open up their designated hitter role to a new player, Schwarber seems like he’d be a great fit.

More MLB: Tigers Tabbed to Trade for $15.5 Million All-Star After Playoff Disaster

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