Normally, over the winter months, there’s somewhat of a general timeline in the MLB as far as blockbuster trades and big-name free agent signings go.
Obviously, fans get a good idea as to which players are hitting the free-agent market after the conclusion of the World Series. Consequently, many MLB executives start the groundwork of productive conversations at the General Managers Meetings, which usually take place in the middle of November. After that, the action starts to happen at the Winter Meetings, perennially held during the first week in December, almost always at a very warm and pleasant venue.