With the World Series ending, all the off-season calendar dates are now fixed. The Winter Meetings are set for December 9-11 and all the "housekeeping" dates (except for arbitration related work) happen before those meetings.
Beginning the day after the Series ends, players eligible for free agency can declare, but not yet negotiate with other teams. There's a five-day period in which teams have exclusive rights to discuss terms with their pending free agents. The Blue Jays only have one, Ryan Yarborough, whom they may well want to re-sign (I would) but they'll likely survey the market first.
Another thing that happens five days after the end of the Series (i.e. Monday November 4) is that qualifying minor league free agents are revealed. In simplest terms, a player acquired during the 2018 season or earlier qualifies (unless they have signed a new contract with their team - as Lazaro Estrada did a couple of weeks ago) as do any player in the system who has been released previously from their "first contract" (which is technically not the first but I'm trying to be simple). For example, Buffalo catcher Payton Henry hit free agency last winter and signed with the Jays. If that was a typical one-year deal (we won't know until the official list is published) then he'll be free again. Similarly, CF Je'Von Ward, who was signed to play in Vancouver this year, was previously released in 2023 which ended his "first contract" which would make him a free agent this winter even if he hadn't played six season in the minors. By my count the Jays' system has at least 14 players eligible for minor league free agency, but the only one(s) you should care about are Eric Pardinho and MAYBE Rainer Nunez. Unless of course they've already signed a new contract that we don't know about.
Also five days out, teams have to reinstate players on the 60-day IL to the 40-man roster. The exit of Yarborough frees up one spot, but the Jays need four, so next week at least three other guys will become free agents. Possibilities for these cuts are waiver-claim relievers Nick Robertson, Brett De Gues, Emanuel Ramirez, Luis Frias, Tommy Nance, and Easton Lucas. Notably Frias and Nance don't have remaining options for next year which would seem to decrease the value of hanging onto them. There are a few other possibilities but I think they will stick longer than this group.
November 19 is the deadline for setting rosters ahead of the Rule 5 draft. There are not very many slam dunks to be added. I've seen some sites list rising prospect LHP Kendry Rojas as needing protection but I think that's wrong. Here's the rule:
Rojas was signed in the fall of 2020, just over a month BEFORE he turned 18. So he's played in four seasons and would not need to be added to the roster until next winter. I count at least 29 players in AAA or AA (anyone in A ball isn't getting selected) that are eligible, but most are guys that wouldn't be considered a significant loss. Lazaro Estrada, having signed a new 2-year contract, would seem likely to be added (else, why re-sign him?). Eric Pardinho might be protected, LH Trent Wallace and C Phil Clarke are dark horse candidates. Of course, each addition means someone is cut. Besides the pitchers already listed above, catcher Nick Raposo or Tyler Heinemann (who's out of options) but not both could be removed, Luis De Los Santos and Steward Berroa likely won't stay on the 40 throughout the winter. There's also the possible early release of arb-eligible guy's who may be non-tendered (more on that next).
The contract tender date is just three days later on November 22. Seems reasonable to guess that Zach Pop and Dillon Tate will not get tendered (though both would be welcome back on minor league deals if they don't get a major league offer this winter). Some speculate about Eric Swanson (I don't think so) and Jordan Romano (which we can't guess without knowing the severity of his medical condition) but there's no point in assuming an exit without knowing. It wouldn't be unreasonable for them to go ahead and clear Pop and Tate on the 19th rather than losing some of those other guys they might feel strongly about.
On December 10, at the Meetings, they'll hold the draft lottery, and the next day the Rule 5 draft. At that point all the shuffling around the margins of the roster will be done. There may or may not be a few open spots for adding free agents but as noted, there are a lot of fungible guys. If you decide to sign, say, Alex Bregman, and you have to wave goodbye to Luis De Los Santos, that's not a complication.
I'll do a separate essay sometime soon about free agency but as a general observation, they need to add another catcher which could be either via trade of FA (I hope it's not just another waiver claim), 2-3 new relievers (depending on Yarborough and whether or not the shock us by cutting Romano) but again, this doesn't HAVE to be free agents, and - so the commonly held wisdom goes - at least one significant hitter at 3B, LF, or maybe DH. As far as I can tell there's only one significant hitter that MIGHT be available via trade, so free agency will likely be a big factor here. Not counting the Soto pipe-dream, I think there's less than a half-dozen guys who might be a difference maker.
This has been sort of a test of my consideration of taking my musings back to relative obscurity. We'll see how it goes. Your thoughts and feedback are always welcome.
