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?

One option would be to designate him for assignment, but that path offers little relief. No team would claim Yoshida at his current salary, leaving Boston responsible for the remaining money. Given how John Henry has historically operated, it is highly unlikely the Red Sox would simply eat the full cost while Yoshida plays elsewhere at a discount.

The last time Boston took that approach was nearly a decade ago. The Red Sox designated Pablo Sandoval for assignment in 2017 while he was in the middle of a five-year, $95 million contract, ultimately paying out roughly $49.5 million. Hanley Ramirez was also DFA’d in May 2018, with Boston on the hook for his $22 million salary, while avoiding a club option that would have vested for the 2019 season had he remained on the roster.

A more plausible path would involve Boston eating a portion of Yoshida’s contract and attaching prospects in a trade. Even then, Yoshida’s salary and defensive limitations would severely restrict his market.

Until Boston finds a creative resolution, Yoshida’s contract will continue to represent one of the clearest obstacles standing between the Red Sox and full roster flexibility heading into 2026.

Another player on the Red Sox’s 40-man roster that the club should consider moving on from is right-handed reliever Jordan Hicks.

Boston owes Hicks $12.5 million in both 2026 and 2027, making a designated-for-assignment scenario highly unlikely. Acquired from the Giants in the Rafael Devers trade, Hicks struggled badly after arriving in Boston, posting an 8.20 ERA across 21 appearances while allowing 12 walks, striking out 15 batters, and finishing with a 1.98 WHIP. Unless Hicks is moved before Opening Day, he is likely to remain part of the bullpen. 

From a tools standpoint, Hicks still checks several intriguing boxes. He ranked in the 92nd percentile in fastball velocity (97.5 mph), the 95th percentile in ground-ball rate (56.7%), and the 93rd percentile in barrel rate (4.7%), according to Baseball Savant. His 23.1% whiff rate and 18.5% strikeout rate both ranked near the bottom of the league, limiting his effectiveness in high-leverage situations.

Ultimately, the most straightforward solution for Boston may be to attach a prospect, eat a portion of Hicks’ remaining salary, and clear his 40-man roster spot. Unless the Red Sox believe they can unlock something within Hicks and get him back on track, he's yet another inflated contract occupying valuable roster real estate — a luxury the Sox can ill afford as it tries to maximize flexibility heading into 2026.

Patrick Sandoval hasn’t thrown a single pitch in a Red Sox uniform yet, and he’s already emerging as a potential trade candidate. The left-hander is coming off a lost 2025 season while recovering from Tommy John surgery, and before Boston aggressively reshaped its rotation this offseason, Sandoval had been viewed internally as a possible back-end rotation option for 2026.

That outlook changed quickly after the Red Sox added Ranger Suárez, Sonny Gray, and John Oviedo making the rotation crowded for the first time in years. As things stand, Sandoval’s clearest path to starting in Boston would require either a standout spring training or an injury ahead of him on the depth chart. 

Prime example, Sean Newcomb had a strong spring last season and was added to 40-man roster securing a spot in the rotation due to injuries to Lucas Giolito and Brayan Bello. If injuries creep up on the rotation this spring, Sandoval provides an insurance plan for Alex Cora. 

While there’s no such thing as too much pitching, keeping Sandoval on the roster comes with complications. The Sox could attempt to make it work by shifting him into the bullpen, where he would give the club another left-handed option competing for a spot. The concern — beyond his recovery from Tommy John surgery — is his $12.75 million salary. 

He's another pitcher that will need to be attached with a prospect to ship him out of town. Boston has had some bites on Sandoval, according to a league source, but nothing is imminent on that front. 

According to his Baseball Savant profile from the 2024 season, Sandoval averaged 94–95 mph with his fastball prior to landing on the injured list, and his extension consistently ranked above league average, allowing his fastball to play up despite not sitting in the upper-90s. 

Boston’s payroll currently sits just south of $270 million, and with additional roster needs still looming before Opening Day, Sandoval increasingly profiles as a viable trade chip. Teams around the league still searching for starting or multi-inning pitching depth could view him as a worthwhile addition, especially if they believe his stuff will fully return post-surgery.

Sandoval last appeared in a major league game in 2024 before landing on the injured list, but his underlying traits — size, velocity, and extension — remain appealing. For Breslow, the decision may come down to whether the Red Sox value that upside more on their own roster or as a means to create payroll and roster flexibility elsewhere.