Masataka Yoshida and Jordan Hicks highlight Red Sox payroll roadblocks heading toward 2026

The Red Sox have dead money weighing down the payroll, and if Craig Breslow can find a creative way to move off some of those commitments, it could unlock far more flexibility for the 2026 roster.

Masataka Yoshida sits at the top of that list. The veteran outfielder has two years and $36 million remaining on his contract, and since signing his five-year, $90 million deal three years ago, he has not lived up to the hype or expectations that accompanied his arrival from Japan.

Over three seasons in Boston, Yoshida has logged 1,206 plate appearances, slashing .282/.337/.425 with a .762 OPS, while totaling 311 hits, 29 home runs, 132 runs scored, and 13 stolen bases. His most productive season came in 2023, when he hit .289 with 15 home runs and a .783 OPS, but his offensive impact has declined since, including a .695 OPS during the 2025 season.

Injuries have also been a recurring issue since Yoshida arrived stateside. After spending his entire professional career in Japan, he struggled at times adjusting to the physical grind of the Major League season. Late in 2023, Yoshida underwent TMJ surgery, an issue that lingered throughout the year. During the 2024 season, he missed time from April through June with a left thumb strain, and in October 2024, he underwent surgery to repair a torn labrum in his right shoulder. That shoulder injury carried into the following season, forcing Yoshida to open 2025 on the 60-day injured list, where he experienced additional recovery setbacks.

That downturn is reinforced by Yoshida’s 2025 Baseball Savant metrics, which help explain why Boston has struggled to generate trade interest. He posted a .314 xwOBA, .270 xBA, and .384 xSLG, reflecting a contact-oriented hitter with limited power impact for a bat-first corner outfielder. While his average exit velocity (90.2 mph) and hard-hit rate (44.0%) were respectable, his barrel rate (6.5%) and overall damage on contact lagged behind league averages at the position.

Yoshida continued to avoid strikeouts — evidenced by an 11.7% strikeout rate and a 15.4% whiff rate — but his 4.9% walk rate limited his on-base upside. Although his squared-up rate (40.7%) and sweet-spot percentage (29.2%) suggest consistent contact, the lack of elite bat speed (71.9 mph) and over-the-fence power leaves more to be desired for a club in need of some additional power sources.

Boston attempted to move Yoshida last offseason, most notably in discussions with the Mariners while searching for starting pitching depth. The Red Sox even explored attaching Triston Casas in a package for right-hander Luis Castillo, but the deal never materialized. Boston wanted Seattle to absorb the remaining money on Yoshida’s contract and believed Casas represented the sweeter asset — but neither side could find common ground, which led to no deal. 

Beyond the contract itself, finding a roster fit for Yoshida has increasingly felt like shoving a square peg into a round hole. He has not played the field consistently due to a combination of injuries and defensive limitations, and when deployed in left field, he has graded out as a below-average defender. That reality has effectively pushed Yoshida into a DH-first role, significantly narrowing his path to everyday playing time.

The Red Sox outfield has become far more athletic since Yoshida arrived in Boston. Wilyer Abreu has established himself as an elite defender, winning two Gold Gloves in right field, while Ceddanne Rafaela captured a Gold Glove in center field last offseason. The continued emergence of Roman Anthony and Jarren Duran has further reshaped the roster, giving Boston speed, range, and defensive versatility across all three outfield spots.

For a club attempting to optimize roster construction and payroll efficiency, a bat-only corner outfielder or DH carrying two years and $36 million on the books is increasingly difficult to justify. 

So how can the Red Sox realistically get out from under the Yoshida deal?