Losing in the wild card round is a tough pill to swallow as it is for the Red Sox. Losing in the wild card round to the New York Yankees is even more frustrating.

Boston knows it needs to improve the roster in multiple ways. Pitching depth behind Garrett Crochet is a vital part of the offseason, but the Red Sox also need to improve their offense. That’s one reason why Jen McCaffrey believes Boston could use Kyle Schwarber as an upgrade at the designated hitter spot.

“Schwarber has spent a majority of the last couple years DHing, but for good reason,” McCaffrey wrote for The Athletic. “He led the National League with 56 homers in 2025 and hasn’t hit fewer than 38 in each of the last four years. If the Red Sox were to pursue him, they’d have to figure out what to do about Masataka Yoshida, who has served mostly as DH and is owed $37 million over the remaining two years of his contract.”

Schwarber is very familiar with playing in Boston and thrived in his short time with the Red Sox a few years ago. Since he left the Red Sox and signed with the Phillies, his bat has become one of the best in baseball. It’s hard to find any player in the game right now with more raw power than he has when he comes to the plate.

If the Red Sox were to bring him in, he would have to bump Masataka Yoshida out of the starting lineup. Like Schwarber, Yoshida is primarily a designated hitter which means the latter would be on the trade block if Schwarber returned to Boston.

The Red Sox have also been connected to Pete Alonso, and the offseason hasn’t even officially started. However, McCaffrey makes the case as to why Schwarber is the better option.

“At 32 and because of his lack of positional flexibility, Schwarber is expected to sign a smaller deal than Alonso, around four or five years and $130-150 million,” McCaffrey wrote. “The Red Sox could absorb Yoshida’s salary (if they can find a trade partner) and still sign Schwarber for about the same it would cost to sign Alonso.”

Given how many holes Boston has to fill this winter, it would make sense to pursue the option that is going to save some money, even if it isn’t much. Getting a player who can hit 50 home runs while also saving money is a win-win for Craig Breslow.

The only possible downside to signing Schwarber would be that he is another left-handed bat in a lineup that is already littered with lefties. However, that should absolutely not stop the Red Sox from pursuing Schwarber.

Sign him, and sort out the rest later.

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