The Boston Red Sox in 2025 returned to the playoffs for the first time in four seasons, but they failed to advance past the Wild Card round. Making it back to October is just the start of Boston's goals, but there's a long offseason ahead with many stops along the way to a revamped squad for 2026.
Chief baseball officer Craig Breslow and the rest of the Red Sox front office were upfront with their intentions to improve the team for next season, which can be done in multiple ways. Boston has more than enough financial resources to sign impactful free agents and plenty of top prospects to trade with.
Free agency and trade decisions, and potentially smaller acquisitions, don't happen overnight. The Red Sox will participate in multiple events that will help them inch toward their goals, and there are dates in the upcoming weeks by which key decisions must be made. Here are all the offseason moments Sox fans should know to stay up to date with everything the team is up to.
Important offseason dates Red Sox fans must know ahead of promising 2026
Qualifying offer deadlines
The day after the World Series ends, which could be anywhere from October 29 to November 2, all eligible players hit free agency. Clubs have until five days after the final World Series game to extend qualifying offers to any eligible players they wish.
Players who have received a qualifying offer have until November 18 at 4 p.m. to decide whether they will accept or decline.
GM meetings
General managers of clubs across MLB will meet in Las Vegas from November 10-13. This gives Breslow an early chance to discuss potential trades with teams that have elite pitching he may be interested in, like the Twins or Brewers. He may also be approached about players the Sox could have on the trade block, like Jarren Duran or Wilyer Abreu, to name a couple.
Rule 5 protection deadline
Teams have until November 18 at 4 p.m. to protect any eligible prospects they wish from the Rule 5 Draft. MLB Rule 5 states that any player who signed with their club at the age of 18 or younger must be placed on the 40-man roster after five years in the minor league system, and players who signned at 19 years or older must be protected within four years. If eligible players are not placed on the 40-man roster to be protected, other teams can select them and place them on their 40-man roster for the entire upcoming season, or they'll be returned to their former team.
The Red Sox have over two dozen prospects eligible for Rule 5 selection this year, but players who are far from MLB readiness are often not at risk to be taken because it isn't worth it to burn a 40-man roster spot on a player teams won't be able to use within the next season or two. Boston could protect top pitching prospect David Sandlin and Triple-A arm Tyler Uberstine, among a few other players, but its 40-man roster is pretty packed already.
Non-tender deadline
This year's non-tender deadline is November 21. Teams can non-tender a player it does not wish to give a contract for the upcoming year, even if they aren't eligible for free agency. Tanner Houck and Nathaniel Lowe are potential non-tender candidates for the Red Sox.
Winter Meetings
Representatives for all 30 teams, agents and media will meet in Orlando from December 8-11 for the Winter Meetings. Last year, Breslow completed trades for Garrett Crochet and Carlos Narváez during the Winter Meetings, and groundwork for more deals could be established this winter.
Other events are held during the Winter Meetings, including the MLB Draft Lottery (December 9) and the Rule 5 Draft (December 10).