3 Players Red Sox Should Pursue This Winter To Bolster Roster: Too Early Edition

The Boston Red Sox are one of the best teams in baseball because of all the aggressive moves they've made this year. Adding Garrett Crochet and Alex Bregman in the offseason bolstered the roster quite a bit, but the additions didn't stop there.

Boston swung a huge trade to cut ties with Rafael Devers before the trade deadline. It also made a handful of other moves to put the team in the perfect position to compete for the postseason. As the season slowly comes to a close, the Red Sox could begin looking toward free agency.

Here are three players the Red Sox could target in free agency in the offseason:

3B Alex Bregman

The first name on the list is obvious. The Red Sox need to prioritize Alex Bregman in free agency, assuming the star opts out of his current contract, which seems like the case.

Bregman will likely look to pursue a long-term deal or another deal with an opt-out after year one. Either way, he is going to be the Red Sox's biggest priority. Bregman has been the best hitter on the Red Sox this season. He's seemingly loved his time with Boston, and the fanbase has seemingly loved him. This is priority No. 1.

DH Kyle Schwarber

Philadelphia Phillies designated hitter Kyle Schwarbe — Sep 13, 2025; Philadelphia, Pennsylvania, USA; Philadelphia Phillies outfielder Kyle Schwarber (12) reacts to his home run against the Kansas City Royals during the fifth inning at Citizens Bank Park. Mandatory Credit: Bill Streicher-Imagn Images | Bill Streicher-Imagn Images

The Red Sox could also pursue designated hitter Kyle Schwarber.

If they lose out on Bregman, Schwarber would be their top option on the market. Stealing him from the Phillies wouldn't be the easiest thing in the world, but the Red Sox have the money to do so.

In a perfect world, the Red Sox would be able to sign Bregman and have enough money to land Schwarber, too. With Devers' $300-plus million coming off the payroll, the Red Sox have more money to spend this winter compared to last. Signing Bregman and Schwarber is a stretch, but it's possible. If Bregman departs, adding the best slugger on the market would fit the Red Sox perfectly.

LHP Framber Valdez

Boston could use another pitcher at the top of its pitching staff. Crochet has been great, but the rest of the rotation has struggled at times. The young prospects have filled in the rotation in a big way, but the Red Sox would likely want to add another top pitcher in free agency.

Adding Houston Astros ace Framber Valdez would fit the Red Sox perfectly, though it would be an expensive move to make.

If the Red Sox are willing to give up around $150 million to $200 million to land Valdez, this idea could work perfectly. It would be the perfect complementary move to signing Bregman or Schwarber to big contracts.

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