Red Sox Must Emphasize Brighter Future To Steal Kyle Schwarber From Phillies

Could this be the winning strategy?

Oct 8, 2025; Los Angeles, California, USA; Philadelphia Phillies designated hitter Kyle Schwarber (12) looks into the dugout after hitting a solo home run during the fourth inning against the Los Angeles Dodgers in game three of the NLDS during the 2025 MLB playoffs at Dodger Stadium. Mandatory Credit: Jayne Kamin-Oncea-Imagn Images | Jayne Kamin-Oncea-Imagn Images

It's very difficult to beat the emotional pull of four years in a certain uniform, and potentially even more difficult to beat out Dave Dombrowski when he wants a free agent.

But the Boston Red Sox simply have to try.

Four years after they let him walk in free agency without much of a fight, the Red Sox have every reason to pursue Philadelphia Phillies designated hitter Kyle Schwarber in free agency this winter. And the best pitch they can make could be best explained by the pit Schwarber undoubtedly has in his stomach on Friday.

Red Sox can claim to have better championship opportunity

Sep 26, 2025; Boston, Massachusetts, USA; Boston Red Sox second baseman Romy Gonzalez (23) runs home to score the game winning run against the Detroit Tigers during the ninth inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images | Eric Canha-Imagn Images

The Phillies were eliminated from the National League playoffs on Thursday night, as reliever Orion Kerkering botched a soft ground ball back to the mound that could have sent their game against the Los Angeles Dodgers to the 12th inning.

For the fourth-straight season, the Phillies fell short of a World Series title when they had a realistic shot to win it. And the Red Sox need to emphasize something plenty of baseball fans sensed on Thursday night -- that championship window in Philadelphia could easily be closing.

Nearly every core player on the Phillies' roster is over 30. Schwarber, J.T. Realmuto, and Ranger Suárez are free agents. Ace Zack Wheeler's health is in question for next season. And they're already $43.5 million ahead of the Red Sox in projected opening day tax payroll, per Spotrac.

The Red Sox are significantly younger than the Phillies, and they've got a burgeoning core that should all be locked in place for the next four to six years. Boston's average position player was 27.6 years old this season (18th-oldest in Major League Baseball), while the Phillies were at 30.3 (second-oldest).

Plus, look at the disparity between the two leagues right now. The Phillies would have been the clear front-runners entering the American League playoffs, but instead, they finished behind the Milwaukee Brewers in the regular season standings and had to face this loaded Dodgers team in their first-round matchup.

Make no mistake: the Red Sox need Schwarber badly. They haven't had a 40-homer bat since J.D. Martinez in 2018. And much like the Martinez signing added the missing piece to a team that won a World Series later that fall, Schwarber returning to Boston would make the Red Sox a powerful force in a wide-open AL.

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