Why Red Sox Should Be Aggressive, Pursue Kyle Schwarber Reunion
September 17, 2025
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The Boston Red Sox are on pace to end a four-year playoff drought after a 2025 season built on improved starting pitching, resurgent veteran leaders and a new crop of young talent.
The last time Boston made the postseason came in 2021 when the Red Sox reached the American League Championship Series and came up two wins short of a trip to the World Series.
PHILADELPHIA, PENNSYLVANIA – JULY 22: Kyle Schwarber #12 of the Philadelphia Phillies runs the bases after hitting a solo home run in the second inning against the Boston Red Sox during a game at Citizens… PHILADELPHIA, PENNSYLVANIA – JULY 22: Kyle Schwarber #12 of the Philadelphia Phillies runs the bases after hitting a solo home run in the second inning against the Boston Red Sox during a game at Citizens Bank Park on July 22, 2025 in Philadelphia, Pennsylvania.
Emilee Chinn/Getty Images
Kyle Schwarber emerged as a massive contributor on that memorable run for the Red Sox. Boston acquired him at the trade deadline while he was on the injured list, knowing his bat would be ready to change games in October.
Schwarber did that with a home run in each round the Red Sox played in to strengthen an already-talented lineup. The 2016 World Series champion walked in free agency that offseason to the Philadelphia Phillies where he’s produced at a ridiculous level on a perennial National League contender.
The slugger helped the Phillies reach the World Series in 2022 and led the National League with 46 homers that year. His power continued and now in a contract year, Schwarber leads MLB with 53 home runs and helped Philadelphia win a second-consecutive NL East title.
The Phillies got everything they could from Schwarber’s contract entering his free agency this offseason. If he hits the open market with several bidders again, the Red Sox should absolutely jump back in the mix to bring him back to Boston.
The Red Sox are in a good spot for their future, but their lineup clearly needs more thump. That’s on display this September with Roman Anthony on the shelf with an oblique injury and Alex Bregman, who could opt-out of his deal at season’s end, in a significant slump in the second half.
Schwarber won’t come cheap, but the Red Sox have money to spend and could have even more coming off the books. Boston already unloaded close to $300 million when the San Francisco Giants took the remainder of Rafael Devers’ contract in June’s blockbuster trade.
Starter Lucas Giolito is a free agent after the year. As previously mentioned, Bregman can opt out of two remaining years as well as shortstop Trevor Story. While Boston would be wise to explore the starting pitching market, both through trades and free agency, the lineup built around young players like Anthony needs more power in 2026.
A short-term, high AAV deal for Schwarber should be a priority for the Red Sox to bump the ballclub from just a playoff team to a true contender with a bright future in 2026 and beyond.
Will Boston push forward the money for a big-ticket reunion this winter?
More MLB: Red Sox Infielder Alex Bregman Urged to Step Up for Final Playoff Push
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