Red Sox Predicted To Trade $90 Million Star In 'Bad Contract Swap' With NL West Team

Would this trade wipe Boston's slate clean?

Sep 25, 2024; Toronto, Ontario, CAN; Boston Red Sox designated hitter Masataka Yoshida (7) hits a double against the Toronto Blue Jays in the fourth inning at Rogers Centre. Mandatory Credit: Dan Hamilton-Imagn Images / Dan Hamilton-Imagn Images

This Boston Red Sox winter feels like it has the potential for fireworks. How about an outside-the-box trade?

These Red Sox have a chance to do something special in 2024, but not if they don't tweak some things here and there. The roster has a ton of talent, but too much of that talent is concentrated in the same areas, like young left-handed hitters and solid mid-rotation starting pitchers.

Designated hitter Masataka Yoshida looms over the entire picture because he signed an expensive contract, doesn't fit the Red Sox's offensive identity, and is currently recovering from labrum surgery. Yoshida is a frequently discussed Red Sox trade candidate, and one insider thinks a deal could get done with the Arizona Diamondbacks.

Chris Cotillo of MassLive recently proposed that the Red Sox could cut bait with Yoshida for one of the Diamondbacks' own underperforming signees, left-handed pitcher Jordan Montgomery.

"Yoshida isn’t without value as he truly was an elite bat-to-ball offensive player against righties for a huge portion of last season," Cotillo said.

"But the Red Sox’ roster fits much better without him. Breslow will likely do everything he can to offload Yoshida, who is even harder to trade now that he’s recovering from shoulder surgery. What about a bad contract swap with Arizona involving Jordan Montgomery?"

Yoshida, 31, is under contract for three more years at $18.6 million per year. He put up just 1.4 wins above replacement in each of his first two seasons despite high batting averages, thanks to a lack of home run power and little added value in the field or on the bases.

Meanwhile, Montgomery, 31, was worth -1.4 WAR just one season after racking up 4.1 between the St. Louis Cardinals and Texas Rangers. He opted into his $22.5 million salary for 2025 because he truly had no other choice after compiling a 6.23 ERA in 117 innings pitched this season.

Bringing Montgomery to Boston for Yoshida feels like a trade with volatile potential outcomes for both sides. But either player could take a leap forward with a change of scenery in 2025, and that feels more likely than succeeding in their current environments.

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