Red Sox Have $37 Million Obstacle To Signing Kyle Schwarber: Insider

Can the Sox clear the hurdle?

Oct 8, 2025; Los Angeles, California, USA; Philadelphia Phillies designated hitter Kyle Schwarber (12) looks into the dugout after hitting a solo home run during the fourth inning against the Los Angeles Dodgers in game three of the NLDS during the 2025 MLB playoffs at Dodger Stadium. Mandatory Credit: Jayne Kamin-Oncea-Imagn Images | Jayne Kamin-Oncea-Imagn Images

Kyle Schwarber would look great in a Boston Red Sox uniform. We know that, because we have photographic evidence.

Schwarber played just 52 games in a Red Sox uniform in 2021, including the postseason. But he made a huge impact on the clubhouse, and that's not a surprise when considering how beloved he's become throughout his four years with the Philadelphia Phillies.

What Schwarber also proved in Philadelphia is that he's one of the premier sluggers in the sport, and the Red Sox now desperately need a bat like his. But in addition to somehow prying him from the Philllies this winter, they have another obstacle standing in their path.

Will Red Sox shed Masataka Yoshida's contract?

Sep 30, 2025; Bronx, New York, USA; Boston Red Sox outfielder Masataka Yoshida (7) hits a two run single during the seventh inning against the New York Yankees during game one of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

On Wednesday, MLB.com insider Mark Feinsand discussed Schwarber's fit for the Red Sox, acknowledging that they could be in the mix to sign him, but explaining that Masataka Yoshida's albatross contract could be a serious roadblock.

"Boston knows all about Schwarber, who posted a .957 OPS in 41 games for the Red Sox in 2021 after being acquired at the Trade Deadline. Schwarber has thrived at Fenway Park in an admittedly small sample size, hitting six homers with a 1.122 OPS in 26 career games in Boston.

"The biggest obstacle to a Red Sox-Schwarber reunion could be Masataka Yoshida, who has two years and $37.2 million remaining on his contract. Yoshida hit well during the final two months of 2025, so if the Red Sox can find a way to trade him, it could open the door for Schwarber to return to Boston."

Yoshida was legitimately one of the Red Sox's best hitters in September and their one postseason series, but it's fair to say his tenure has been a disappointment thus far. The Red Sox would have to eat a high percentage of the money on that deal to trade him, and the money is the real sticking point over finding a team that will take him.

If the Red Sox are serious about being World Series contenders, they'll not just be willing to eat money on a Yoshida trade, but to waive him and swallow the entire $37 million on top of whatever they'd pay Schwarber.

But first, they would need to convince Schwarber to leave the organization that's loved him for the last four years.

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