The Red Sox have six weeks of the regular season and a potential postseason appearance to worry about first and foremost, but the issue of Alex Bregman's future with the team is going to be an underlying question through October regardless of the team's performance.
Bregman will have to choose whether or not to opt into the second year of his deal in Boston by Nov. 3, the Monday after the conclusion of a potential World Series Game 7. The prevailing sentiment is that he'll opt out and explore the market again for a more favorable deal — unless the Red Sox actually manage to extend him before that date.
Reports on the front office's progress with him regarding this have been mixed, but Bregman himself seemed to confirm that he's not entertaining in-season discussions.
Per Tim Healey of the Boston Globe, Bregman said, "Obviously, we're open to talking [when the season is over]. But for the next few months, I’m just really focused on the baseball. I'm just focused on trying to do what I can to help this team win and get into the playoffs. I feel like that's where my head and mind need to be."
Alex Bregman doesn't want to talk about a Red Sox extension until the season is over
A deep postseason run would do a lot to convince Bregman to stay in Boston, but a refusal to engage earnestly in extensions until the season is over could also limit the amount of time Craig Breslow and the front office has to convince him to spend the rest of his career with the Red Sox.
If the way Bregman's free agency played out in the offseason is any indication, his agent Scott Boras isn't going to let him settle for anything less than the best. There will certainly be takers if he opts out, and they might still be willing to give him the years he's looking for despite his injury-shortened 2025.
Even if he does simply exercise his 2026 option to stay for another season, which seems unlikely, the front office will have to do this all over again next offseason if they come to an impasse on extension talks. As it stands, it looks like Breslow is going to be scrambling the second the season concludes. There will be other issues for them to address in the offseason, but Bregman was always going to be first priority, and it won't help when a number of other teams are in line looking to pay top dollar.