MLB Insider Reveals ‘Biggest Obstacle’ In Red Sox’s Kyle Schwarber Pursuit

The Boston Red Sox are entering a crucial offseason, and after making an unexpected run to the playoffs in 2025, the belief is that they will be active in adding players to their team over the next few months.

One guy who stands out as an obvious target in free agency is Kyle Schwarber. One of the top power hitters in the game, Schwarber has familiarity with Boston after spending the second half of the 2021 campaign with the team, as he played a leading role in helping that squad advance all the way to the ALCS.

Schwarber bolted for the Philadelphia Phillies in free agency after his brief stint with the Sox, but now that he’s back on the open market, Boston is expected to be one of his top suitors over the coming weeks.

There are a couple of roadblocks that could prevent the Red Sox from making a serious push for Schwarber, though. In the eyes of MLB insider Mark Feinsand, he believes that Masataka Yoshida’s presence could ultimately deter the team from making a run for Schwarber.

“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,” Mark Feinsand wrote for MLB.com. “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.”

Given the current makeup of Boston’s roster, it’d be tough to fit him into the picture currently, but depending on what other moves are made, that could change very quickly. Schwarber’s familiarity with the Red Sox makes him a very popular free agent target, and it will be interesting to see how heavily the team ends up pursuing him.