Aug 16, 2023; Toronto, Ontario, CAN; A Philadelphia Phillies cap and glove sit in the dugout during a game against the Toronto Blue Jays at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images John E. Sokolowski-Imagn Images

Phillies Superstar Could Defect In Favor Of Red Sox Reunion: Insider

Originally posted on Boston Red Sox on SI
By Jackson Roberts | Last updated Sep 5, 2025 10:00 AM ET

Perhaps no team has a wider range of outcomes on the table this winter than the Boston Red Sox.

If there are no marquee signings and Alex Bregman departs Boston, fans will rightfully be livid. However, thanks in part to the money saved from the Rafael Devers trade, there's a chance the Red Sox could fill out their roster with some true offensive impact.

If Bregman is returning to play third base, Boston would likely seek an impact first base/designated hitter type. It just so happens that they had one of those at this time four years ago, and let him sign with the Philadelphia Phillies.

Kyle Schwarber-Red Sox reunion?

Kyle Schwarber was a fantastic pickup for the Red Sox at the 2021 trade deadline, and he's only gotten better in his four seasons with the Phillies. In a career year leading into his free agency, he's belted 49 home runs and posted a .935 OPS through 140 games.

On Thursday, Jon Heyman of the New York Post listed the Red Sox as a potential destination for Schwarber, though it appeared the insider still believed the Phillies were the favorites to retain his services.

Schwarber, 32, will be one of the most expensive DH-types ever to sign a long-term deal. He made his third All-Star team this year, and although he's probably never going to play more than a handful of games on defense in any season moving forward, he can completely change the outlook of a lineup.

If the Red Sox can grab Schwarber for something like four years, $140 million and keep Bregman for $200 million or less, they might have the scariest lineup in the American League. That seems like a reasonable ask from an ownership group that's been spending like crazy on Liverpool F.C.

The blueprint is available for the Red Sox to build the most dominant roster in the AL for the next half-decade. But until November arrives, the uncertainty of Bregman's potential departure and who else Boston will pursue lurks.

This article first appeared on Boston Red Sox on SI and was syndicated with permission.

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