If the Boston Red Sox are hoping to bring slugger Kyle Schwarber back in free agency, they’ll have to clear a major obstacle in their path.

Schwarber had a fantastic four-year tenure with the Philadelphia Phillies, culminating in a career year with a National League-best 56 home runs. That’s exactly the type of power output the Red Sox are craving nowadays, but why should the Phillies let him walk away?

The Red Sox could have a tall task when it comes to outbidding the Phillies in the Schwarber sweepstakes, and one insider threw some cold water on the idea that such a task could be accomplished on Tuesday.

Phillies likely all-in on keeping Schwarber

Oct 8, 2025; Los Angeles, California, USA; Philadelphia Phillies designated hitter Kyle Schwarber (12) hits 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

Jon Heyman of the New York Post wrote Tuesday that Schwarber was expected to be “a top priority” for Philadelphia, and included an anecdote from a rival executive that furthers the notion that the Red Sox will have a tough time.

“The Phillies are making Kyle Schwarber a top priority,” Heyman wrote. “‘I doubt (baseball president Dave Dombrowski) lets him leave,’ one rival said. The Red Sox, who also love him, make sense, as might his original Cubs.”

Optimists can point to the fact that the Red Sox continue to be linked to Schwarber as cause for keeping the faith. But it feels right now as though the Phillies will have to severely underestimate the market for the three-time All-Star (i.e. what the Red Sox are willing to offer) in order to lose him.

While the Red Sox have kept their purse strings tight in several recent offseasons, the fact that Schwarber could be available on a shorter contract than, say, Alex Bregman, could be a reason for Boston’s front office to bid heavily on his services.

Then again, Schwarber would clog up the designated hitter spot, which was theoretically one of the reasons the Red Sox got rid of Rafael Devers in their most shocking transaction of the past year.

It’s just not easy to envision the Red Sox blowing the Phillies’ offer out of the water, whichever angle from which we examine the situation. But as long as Boston has a seat at the table, the dream of more Schwarbombs at Fenway Park lives on.