Coming off their first playoff appearance since 2021, the Boston Red Sox are gearing up for a critical offseason as they look to improve their team for 2026.

Two of their top free agent targets will likely be former Red Sox sluggers Kyle Schwarber and Alex Bregman, both of whom were All-Stars this season.

Schwarber briefly played for Boston in the second half of 2021 before signing a four-year, $79 million deal with the Philadelphia Phillies. His contract is up, making him a free agent again at age 32 after leading the National League in home runs and RBI this year.

Meanwhile, Bregman is reportedly planning to opt out of the remaining two years and $80 million on his contract after spending 2025 with the Red Sox. Like Schwarber, he’s expected to receive a bigger contract this winter.

MLB insider Jon Heyman believes both sluggers will reunite with their current teams.

Story continues below advertisement

.@JonHeyman’s top 5 teams for Kyle Schwarber:

1. Phillies
2. Cubs
3. Red Sox
4. Blue Jays
5. Giants

“To me, (Philly) is the logical destination. Even more likely than Bregman back to Boston, which I think is pretty likely.” pic.twitter.com/6qcFerlldN

— Gordo (@BOSSportsGordo) October 17, 2025

“To me, (Philadelphia) is the logical destination (for Kyle Schwarber). Even more likely than Bregman back to Boston, which I think is pretty likely,” Heyman said earlier this week.

Schwarber is coming off a career year with the Phillies, who probably don’t want to repeat the Red Sox’s mistake of losing him in free agency. Dave Dombrowski has a history of being aggressive when it comes to re-signing or extending his stars, so it’s hard to envision him letting Schwarber walk and leave a massive hole in the middle of their lineup.

Story continues below advertisement

Meanwhile, Boston is considered the favorite to sign Bregman, who enjoyed his time there this season and was a great fit in the clubhouse. The Red Sox should also be extra motivated to keep him after trading fellow third baseman Rafael Devers last summer.

So while Schwarber and Bregman could both sign elsewhere, it seems more likely that they’ll stick around.

Story continues below advertisement