General Managers meetings
It's standard for all 30 general managers (or presidents of baseball operations) to meet each year in November. This year, those meetings are scheduled for November 5-7 in San Antonio. Major deals or transactions typically don't happen at these meetings; however, the heads of baseball operations are able to begin discussing players of interest or valuation of players in trades.
40-man roster deadline
40-man rosters must be finalized this year by November 15. This would include activating players on the 60-day Injured List and placing players who are eligible for the Rule 5 Draft on the 40-man roster. This year, by my calculations, the Cardinals have 48 players who could be added to the 40-man roster. Obviously, not everyone will be added, but players like Tink Hence, Tekoah Roby, Matt Koperniak, and Matt Svanson are names of players who could be added.
Any player not added to the 40-man roster by November 15th will be eligible for the Rule 5 Draft.
Non-tender deadline
This year's deadline to tender contracts to players without multi-year deals or who aren't on the 40-man roster falls on November 22nd. Any player not offered a contract by November 22nd will become a free agent at the end of the day. The Cardinals and these players could still negotiate new deals if an agreement isn't reached by the deadline.
MLB's Winter Meetings will occur in early December.
This is where most of the wheeling and dealing will occur this offseason. The Winter Meetings are where reporters, fans, aspiring journalists, and club officials convene each year for a few days. Historically, this is where trades will occur or become close to finalized. The event is scheduled for December 9-12 in Dallas this year. Free agent signings could also occur, as player agents are in attendance each year, too.
The Rule 5 Draft has also historically taken place on the final day of the Winter Meetings. The players who were eligible for the Draft who were not added to the 40-man roster by November 15th are now eligible to be plucked by opposing teams. In 2024, the Cardinals selected a number of players via the Rule 5 Draft, but only Ryan Fernandez from the Boston Red Sox made contributions to the major-league squad.
Any player drafted in the Rule 5 Draft must be added to the team's active roster or his rights will return to the prior team. Any players the Cardinals draft and activate via the Rule 5 Draft will also cost them $100,000, awarded to the team losing that player.