It's going to be a complicated offseason across Major League Baseball, to say the least. The current collective bargaining agreement is set to expire on Dec. 1 and then it's anyone's guess what will happen across the league.

The Boston Red Sox are in an intriguing spot. Arguably, Boston is in a significantly better place right now than it was at this point last year. That's thanks in large part to the deals to bring Adley Rutschman and Curtis Mead to town before the trade deadline. Both are under team control in 2027. So, Boston doesn't need to think about adding another elite catcher or second baseman. When the 2027 season begins — whenever that may be — the vast majority of the Red Sox's roster will likely look as it did during the 2026 playoffs.

There will surely be additions — and likely a few exits — but the Red Sox don't need to reinvent the wheel here. Still, a likely lockout will expedite things. Within five days of the World Series coming to an end, the Red Sox will have to make option decisions, like whether to pick up their end of Sonny Gray's mutual option. That certainly isn't likely. But an official decision must be made. Then, there will be roughly one month between the end of the World Series and Dec. 1 to take care of business. For the Red Sox, the biggest guy to watch is Jarren Duran. Will this be the offseason Boston moves him after years of rumors? Well, fans likely won't have to wait too long to find out. Typically, you see the offseason start off slowly and then things really heat up at the Winter Meetings.

What Will Boston Do?

Currently, the Winter Meetings are scheduled to take place between Dec. 7–10 in Orlando, Florida. But that could certainly change. Unlike previous years, expect to see movement across the league well before then. Super agent Scott Boras made the argument that it will be best for teams to sign guys before the new CBA. This is a guy who represents some of the top talent in the league, including Tarik Skubal, who could command a historic deal this winter. If he's already making that point in October, expect to see movement early.

If the Red Sox are going to flip Duran this offseason — or anyone for that matter — the month of November is the time to watch for, instead of December or January. Boston also needs some more power, like as a designated hitter. The same can be said of additions, as well as potential subtractions. Rather than waiting for the Winter Meetings, expect to see Boston surveying the market much sooner than you'd typically expect.

When December 1 arrives, there's no telling when baseball will be played, if a new CBA hasn't been agreed to by then. ESPN's Jeff Passan was asked whether a World Series featuring the Milwaukee Brewers and Tampa Bay Rays will have any impact on the league's or MLBPA's stance on a salary cap — or lack thereof. He shut down the idea. A labor fight is coming and the only way through is compromise, which neither side has proven it's willing to do yet. If a player is still available in free agency on Dec. 2, there's no way to know when they will even have the chance to sign deals. So, expect movement quickly. For Boston, that could mean adding a bat, or maybe even cutting ties with Duran, among others.