As MLB free agency begins today, here’s a look at the 2026-2027 MLB Offseason Calendar

November 2: Free Agency Begins

Hot damn, that’s today!

It’s been five days since the World Series ended, so that means that, as of 5 PM, the Red Sox’ exclusive window to negotiate with free agents will close and the market will officially open up. In recent years the free agent market has moved about as quickly as Wilson Contreras on a bum leg. But in light of the pending labor situation (more on that below) we could actually see a flurry of early signings.

In addition to free agency opening, all players currently on the 60-day IL will be moved to the 40-man roster (which means the Sox will still need to make some cuts), and teams must decide whether to extend any qualifying offers to pending free agents.

Interestingly, the Sox will only see 3 players from the 2026 team head to free agency: Sonny Gray, Patrick Sandoval, and Isiah Kiner-Falefa.

November 9-12: GM Meetings

Yes, we still call these the GM meetings, even though title bloat as made the actual title of “GM” more or less irrelevant. Nevertheless, MLB’s various POBOs, CBOs, and SVPs will gather in Las Vegas to float some trade ideas and, I don’t know, check out the Backstreet Boys residency or whatever. Traditionally, these meetings generate a lot less player personnel moves than the later winter meetings, but in light of the fact that the winter meetings may be canceled, that might be different this year.

November 17: Rule 5 Protection and Qualifying Offer Deadlines

Five days after the GM meetings, the Sox will have to decide which Rule 5 draft eligible players to protect by adding them to the 40-man roster. There are a number of Red Sox minor leaguers who are eligible for the Rule 5 draft. But because anyone selected in that draft subsequently needs to spend the entire 2027 season on an MLB roster or be sent back to the Sox, the only players truly impacted by this are those who are legitimately close to the big leagues. For the Sox, this includes players like Braiden Ward, Mikey Romero, Johanfran Garcia, and Blake Wehunt.

This is also the deadline for players who received qualifying offers to either reject or accept them. There isn’t much suspense for the Sox here, either. Sonny Gray will be the only player to receive an offer, and he will not hesitate to reject it.

November 17-19: MLB Owners Meetings

Another annual event that doesn’t tend to generate much player movement, this year’s version will be notable for what we hear about the pending labor war.

November 20: Non-Tender Deadline

All players with fewer than 6 years of MLB service time (that is to say, all arbitration-eligible and pre-arbitation players) must be offered an MLB contract by their teams by this deadline, lest they become free agents. The Red Sox have a lot of players who fall into this bucket:

There have been whispers that Jarren Duran could be non-tendered, but that is highly unlikely. So long as the Sox think they could conceivably trade one of the above players, then it doesn’t make any sense whatsoever to non-tender them, even if said player isn’t necessarily a part of Craig Breslow’s plans for 2027.

December 1: CBA Expires, Despair and Darkness Set In

And on this day, the owners will initiate the much-dreaded lockout, putting a halt to any and all baseball activity until a new CBA is agreed upon by the owners and players union. Matt Gross has already explained why this will happen:

The real reason the owners want a cap is because they need a line on a graph to go up. Nothing more, nothing less. Valuations of franchises tend to be much higher when you get to put a limit on how much you pay the guys who make your product magical, and since baseball has and always will reflect the American reality, we now get to sit back and watch as a small group of billionaires prepare to make life worse for everybody else.

The Winter Meetings, the MLB Draft Lottery, the Rule 5 Draft, and the arbitration period are all liable to be canceled. Spring Training may not start on time or even take place in spring. And, of course, the entire 2027 will be put in jeopardy. Hope you like winter, because we’re in for a loooooong one.