THE ULTIMATE FLOP: Masataka Yoshida Tagged as Red Sox’s No. 1 Trade Candidate—The $90 Million Headache No One Wants to Admit.vc

(BOSTON) — The Boston Red Sox are facing a painful reality that General Manager Craig Breslow may have to confront head-on this winter: the ultimate organizational flop of the Chaim Bloom era. Outfielder and Designated Hitter Masataka Yoshida, who was signed to a staggering five-year, $90 million contract before the 2023 season, is now being widely tagged by insiders as the team’s No. 1 trade candidate—a shocking necessity that Red Sox Nation is desperate to ignore.

The high-price, low-production veteran has become the team’s biggest financial headache, and the organization is now looking for a way out.

The Flop: $90 Million for Limited Production

Yoshida’s performance over the last two seasons has consistently fallen short of the lofty expectations set by his contract:

• Injury and Output: After a decent rookie year, 2024 and 2025 were marred by injuries, including shoulder surgery that limited him to just 55 games in 2025. When healthy, his power output was inconsistent, and his overall defensive value was non-existent, pushing him primarily into a Designated Hitter role.
• The Logjam: The emergence of homegrown outfield talent—Jarren Duran, Wilyer Abreu, and Ceddanne Rafaela—has created a critical logjam. Yoshida, due $37.2 million over the next two seasons, occupies a DH spot that the team needs to fill with higher-power production (e.g., free agent Kyle Schwarber).

The Shocker: Breslow Forced to Shop

The consensus among MLB insiders, including those at Sports Illustrated, is that while Breslow may want to find a solution in-house, the trade market is the only clear answer to fix the roster imbalance.

“Yoshida is the most logical candidate to be used in a deal for pitching,” stated one reporter, highlighting the team’s dire need for starting rotation help.

However, the team faces an agonizing dilemma—the “shocker no one wants to admit”: The Red Sox will likely have to eat a significant portion of Yoshida’s remaining salary to facilitate any trade. Teams are unwilling to take on a full $18+ million salary for a DH-only player with recent injury history.

Trading Yoshida, even at a cost, would free up the crucial DH slot and the much-needed payroll flexibility that Breslow requires to acquire the elite talent he has promised to bring to Fenway Park. The decision to offload their $90 million man defines the aggressive shift in Boston’s front office philosophy.