Boston Red Sox Offseason: Key Dates to Know For 2026-27

After defeating the Tampa Bay Rays 4-1 in Game 5 on Wednesday night, the Milwaukee Brewers are World Series champions for the first time in franchise history. With the offseason officially underway, the Boston Red Sox have a lot of work to do ahead of the impending lockout to build a World Series-contending team. 

Here are the key dates that you need to know about heading into the offseason: 

Free agents are removed from their former team's 40-man roster. For the Red Sox, this means that Patrick Sandoval and Isiah Kiner-Falefa are no longer on the Boston 40-man roster. Free agents can exclusively negotiate with their current teams, but cannot sign with other teams yet.

Trades also open up for the first time since the trade deadline. 

For the Red Sox, Nov. 2 marks the first day to make major decisions. The team must decide on Garrett Whitlock's team option for the 2027 season and Sonny Gray's mutual option. The Red Sox will also have to trim four players from the 40-man roster as seven players return from the injured list. 

Teams will also have to decide whether to issue a qualifying offer to their free agents. Because Gray has an option, he is not eligible for a qualifying offer. Free agents can also sign major league contracts with new teams beginning at 5:00 p.m. ET. 

Heads of baseball operations across the league will convene in Las Vegas, Nev., for the general manager meetings. Last season, Red Sox Chief Baseball Officer Craig Breslow outlined his offseason plans at the GM meetings, including pursuing a No. 2 starting pitcher behind Garrett Crochet and a right-handed power bat. 

This date matters less for the Red Sox, as they won't have any players making qualifying-offer decisions. However, players who receive a qualifying offer must decide by 4:00 p.m. ET whether to accept the one-year, $23.15 million contract and return to their previous teams. 

The Red Sox must decide whether to protect anyone from the Rule 5 draft by adding them to the 40-man roster. However, with the lockout threatening both the Winter Meetings and the Rule-5 draft, teams could take a calculated risk and protect no one, hoping the draft will be canceled or rescheduled after the lockout, with a new deadline to protect players. The 2022 Rule-5 draft was canceled amid the labor dispute. 

Teams will have until 8:00 p.m. ET to tender contracts to any arbitration-eligible or pre-arbitration players. The Red Sox have 17 arbitration-eligible players and 15 pre-arbitration-eligible players. Any player who is not tendered a contract immediately is released and becomes a free agent. 

At 11:59 p.m. ET. the collective bargaining agreement will expire. Unless something like a miracle happens and the two sides agree to a new deal, the owners are expected to lock out the players. Once the lockout begins, teams can't contact anyone on their 40-man rosters; free agency and trades pause.