The offseason has officially begun for all 30 teams across Major League Baseball and we're just days away from the first big decisions being made.
Within five days of the World Series coming to an end, option decisions must be made by players and clubs around the league. For the Boston Red Sox , they have two option decisions to make: Sonny Gray and Garrett Whitlock.
Gray has a $30 million mutual option that is significantly more likely than not to be declined by one side. Mutual options almost never get accepted. Gray's will likely not be any different. When it comes to Whitlock, things are different. He has an $8.25 million club option for the 2027 season. It's all but guaranteed that Boston will pick up Whitlock's option. We're talking about a guy who just had a 1.72 ERA and a 59-to-9 strikeout-to-walk ratio in 52 1/3 innings pitched. Whitlock is pretty much guaranteed to be back in 2027. Gray is up in the air.
Sep 23, 2026; Boston, Massachusetts, USA; Boston Red Sox pitcher Garrett Whitlock (22) delivers a pitch against the Cleveland Guardians during the eighth inning at Fenway Park. Mandatory Credit: Gregory Fisher-Imagn Images | IMAGN IMAGES via Reuters Connect
Beyond these two, Boston will have to trim its 40-man roster down as well. There are technically seven moves to be made because of all the injuries that impacted the club in 2026. Isiah Kiner-Falefa and Patrick Sandoval are both going to free agency, so that will take care of two of them. Gray is very likely to join them , which would be a third. After that, the Red Sox will have to trim the 40-man roster down four more spots within five days of the World Series.
So, by Monday, Nov. 2, the Red Sox have to make option decisions and get their 40-man roster back down to compliance. It's going to be a busy few days, to say the least. And the movement won't stop there. Typically, you tend to see offseasons start slowly, but clubs around the league will not have that luxury this year.
The 2026 MLB season was great from start to finish, but now the game is completely up in the air. Come December, we're very likely to see a lockout in Major League Baseball and then there's no way to know when we will see games again. Between now and December, clubs have to get their rosters in order so when baseball does return, they aren't behind. Boston has just a few days to get the offseason started. After that, it's going to be a sprint until December.
This article was originally published on www.si.com/mlb/red-sox/onsi as Red Sox Just Days From Big Sonny Gray, Garrett Whitlock Decisions .
