The 2025 Major League Baseball regular season is winding down and the Boston Red Sox are facing two questions as they try to make a return trip to the playoffs for the first time since 2021.

The first is in reference to the starting rotation. Boston’s rotation has been ravaged by injuries all season. Right now, the only three guarantees for the Red Sox are Lucas Giolito, Garrett Crochet, and Brayan Bello. Injuries have been popping up all year for the club, including Kutter Crawford, Tanner Houck, Richard Fitts, Hunter Dobbins, and Dustin May among others.

Boston will have to work through the rotation questions throughout the rest of the season with young guys playing a big role before figuring things out this upcoming offseason.

The other big question is firepower in the starting lineup. Boston obviously traded Rafael Devers this summer, but Roman Anthony help make up for his loss. Now, Anthony is out as well to go along with Wilyer Abreu.

Sep 14, 2025; Philadelphia, Pennsylvania, USA; Philadelphia Phillies designated hitter Kyle Schwarber (12) hits a home run against the Kansas City Royals in the first inning at Citizens Bank Park. Mandatory Credit: Kyle Ross-Imagn Images / Kyle Ross-Imagn Images

Boston has just two players with over 20 home runs right now with Trevor Story at 24 and Abreu at 22. Alex Bregman has 17 and would likely be over that threshold if he hadn’t missed time earlier in the season. Boston’s offense could use a boost right now and this will likely be a topic for the offseason as well.

Trading Devers freed up a lot of money for the organization. So, this offseason, the Red Sox should do everything possible to keep Bregman around. Plus, on top of that, add more power. Recently, there’s been a lot of buzz about the possibility of Boston reuniting with Kyle Schwarber. He has 52 home runs for the Philadelphia Phillies and is heading to free agency. FanSided’s Robert Murray is someone who has talked about the possibility of the Red Sox and Schwarber reuniting, among others.

The Phillies have made it clear that they are interested in keeping Schwarber, but the slugger at least opened the door to the possibility of leaving while speaking to Jon Heyman of the New York Post.

“If something works out here, it works out here. There’s interest on both sides,” Schwarber said. “I’m sure whenever we get to the end of the year, and hopefully it’s us holding a trophy at the end, I’m sure there’ll be conversations…Sometimes hopes and dreams don’t turn out the way they’re meant to be.”

Baseball is a business and it’s not shocking that Schwarber at least talked about the idea of other options. Most of the buzz around him has been about returning to Philadelphia. But, if he enters free agency without an extension in Philadelphia, he should be a top option for Boston. A lineup featuring both Bregman and Schwarber along with guys like Trevor Story, Anthony, Marcelo Mayer, Jarren Duran, and Ceddanne Rafaela among others would be very good in 2026 and beyond.

It’s early to be talking about free agency, but Boston should be watching Schwarber very closely.

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