Red Sox's 'Biggest Obstacle' For Kyle Schwarber Shouldn't Stop Them

An old friend of the Boston Red Sox is out there for the taking right now in free agency.

Kyle Schwarber is one of the best overall players out there looking for a new home right now. He should get paid well this offseason. He had a four-year, $79 million deal with the Philadelphia Phillies and significantly outperformed it. In 2025, he clubbed 56 homers and drove in 132 runs.

Schwarber is a star and is someone the Red Sox know well after he was with the team back in 2021 before he went to free agency. With the Red Sox needing a power boost, unsurprisingly, his name has been brought up. MLB.com's Mark Feinsand, for example, mentioned Boston as a fit for Schwarber. But, he called Masataka Yoshida the Red Sox's "biggest obstacle" for a deal.

"Red Sox," Feinsand said. "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.

Should the Red Sox pursue Kyle Schwarber?

Oct 9, 2025; Los Angeles, California, USA; Philadelphia Phillies left fielder Kyle Schwarber (12) reacts after a double in the first inning against the Los Angeles Dodgers during game four of the NLDS round for the 2025 MLB playoffs at Dodger Stadium. Mandatory Credit: Jayne Kamin-Oncea-Imagn Images | Jayne Kamin-Oncea-Imagn Images

"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."

This makes a lot of sense. Yoshida was primarily used as a designated hitter in 2024. In 2025, he mainly was used as a DH, but got a little bit of playing time in the outfield when he fully recovered from offseason shoulder surgery.

Schwarber is someone the Red Sox tried out at first base in his brief run in Boston, but he's pretty much a DH at this point in his career. Yoshida has two years left on his five-year, $90 million deal. If the Red Sox want Schwarber, something would have to be done with Yoshida afterward. A trade would be the best-case option in that scenario, but he doesn't have much trade value at this point after missing a lot of time in 2025 and not much defensive upside.

It shouldn't stop Boston from pursuing Schwarber, but Yoshida would be the biggest question mark afterward if it could get him. There are options the Red Sox could take if they signed Schwarber. They could trade Yoshida, but that may not be very likely or they would have to eat cash in the process. Boston could cut ties with him by designating him for assignment, although that also would cost a lot of cash. The Red Sox could also keep him as an expensive bench bat and mix him in the outfield as well.

It's not shocking that Yoshida is viewed as the "biggest obstacle," but there are options. When there is a guy available who just hit 56 homers, you should go after him and figure out the other details later.

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