Red Sox Get Kyle Schwarber Contract Update From MLB Insider

Here's what it will almost certainly take to have a shot at the slugger

Oct 8, 2025; Los Angeles, California, USA; Philadelphia Phillies designated hitter Kyle Schwarber (12) congratulated in the dugout after hitting a solo home run in the fourth inning against the Los Angeles Dodgers of 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 appears Kyle Schwarber has seized the title of "most coveted free agent" this offseason, and the Boston Red Sox, at the very least, are in the hunt.

Schwarber just had a 56-homer season for the Philadelphia Phillies, making the fourth year of the Red Sox wishing they'd kept him after his half-year stint in Boston quite possibly the most painful one. Now, the Sox finally have a chance to right their wrong.

There are a lot of obstacles in their way, however, and ESPN insider Jeff Passan summarized where things stood with Schwarber on Friday, with a major update on the kind of contract it would take for the Red Sox -- or any of the slugger's other suitors -- to get a deal done.

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Schwarber seems destined for 5-year contract

Passan's main takeaways were that it would likely take a five-year contract for any team on Schwarber's list to win the sweepstakes, and that the Red Sox were among a handful of teams waiting on his decision, for better or worse, before having the ability to move on to other pursuits.

"When does the Kyle Schwarber dam break? Several teams' fortunes -- from Philadelphia to (the Cincinnati Reds) to (the Pittsburgh Pirates) to Boston to (the Baltimore Orioles) to the New York Mets -- depend on where Schwarber goes," wrote Passan.

"The belief among teams is that it will take five years to secure the 32-year-old, and once that happens -- perhaps sometime during the meetings -- teams will start pivoting, and the action will pick up demonstrably."

It seems at times as though the Red Sox are most concerned about what a signing does to their luxury tax payroll this season as opposed to the number of years on the deal. That said, paying Schwarber through his age-37 season could be unappetizing for this Boston front office, which hasn't been willing to pay virtually any stars that late into their careers of late.

It's hard to overstate what getting Schwarber back would do for Boston's offensive outlook. But is there realistically any shot of them outbidding the Phillies?

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