The Boston Red Sox need a dose of power (and more) to round out their offense, and a reunion with free agent slugger Kyle Schwarber could be the fastest path to adding 40-plus homers to the lineup.
Despite his veteran status, Schwarber has his fair share of suitors early in this offseason's market. MLB insider Jeff Passan reported on November 30 that Schwarber could be the first of the winter's biggest free agents to sign, and that he expects the 32-year-old to secure the contract length and price his team demands.
Per Passan's report, the Red Sox are still bringing up the rear in the Schwarber chase. He tabbed a reunion with the Phillies, his team of the last four years, as the most likely outcome of his stint on the open market. Passan also noted that the Red Sox, Reds and Mets are in the mix for Schwarber's services — the slugger may even be dropping hints that he wants the Reds, the team he grew up cheering for, to land him in the end.
Fellow MLB insider Jon Heyman reports that there are other teams in the chase to sign Schwarber, one of which presents a much bigger concern for Boston. The Orioles are reportedly pursuing Schwarber to address their need for a power bat, either in the first base or designated hitter slot (subscription required).
Red Sox and Orioles in the running for Kyle Schwarber amid reports of likely Phillies reunion
Baltimore already added 30-plus homers to its outfield after the trade addition of Taylor Ward, and president of baseball operations Mike Elias has been vocal about his desire to bring in a top free agent, as well. Adding Schwarber to the Orioles' lineup would be dangerous for the Sox, who haven't added any pop yet.
Schwarber clobbered a career-high and National League-best 56 home runs in 2025 and he led MLB with 132 RBI. If Gunnar Henderson rebounds and approaches the success he had in his 2024 All-Star season when he mashed 37 home runs, Baltimore could have one of the most powerful offenses in the American League East. Schwarber in the lineup alongside a healthy Tyler O'Neill would also be frightening for opposing pitchers (that's a big ask, considering O'Neill has averaged less than 89 games in the last four seasons).
Before the offseason officially began, Scott Lauber of the Philadelphia Inquirer reported that Schwarber could seek a five-year deal, which is quite long for a player who will be 33 on Opening Day. The Orioles and Red Sox have the funds and the competitive window to take such a risk, however, and the door is open to both of them after recent reporting that he and the Phillies aren't close on a new deal.
If Baltimore lands Schwarber, it'll have some early catch-up to play within its division. The Blue Jays added Dylan Cease to their rotation (shortly after the Sox traded for Sonny Gray), and the Orioles will have added around 80 homers to their offense with Ward and Schwarber in the lineup. Passan's update suggests Schwarber could be headed for a deal over the upcoming Winter Meetings, and the Red Sox should be among his suitors until the end.