The New York Yankees' 40-man roster currently sits at 36, meaning fans are either about to get extremely enthused or extremely disappointed.
Moves must be made, both to facilitate a complete overhaul and to legally fill out the roster. New additions are coming. But when? And at what magnitude?
The MLB offseason could get in gear during Thanksgiving Week. It's happened before. Curt Schilling famously head-nodded at his trade to the Red Sox during Feast Week 2003, ruining our lives forever. But the real frenzy typically gets going when the game's most important parties reunite at one of America's grand hotels for the Winter Meetings, after laying the groundwork at the GM Meetings a few weeks earlier.
You remember those, right? Brian Cashman went insane? Well, now he's back for Round 2.
What are the Winter Meetings?
The Winter Meetings will take place Dec. 4-7 in Nashville this time around, and will gather the league's top decision-makers (GMs, Presidents of Baseball Operations, etc.) under the same roof with a cabal of power brokers and a fleet of reporters.
Scott Boras will certainly be there. He'll likely do another cryptic press conference where he babbles on about how Cody deserves a fatter Belli, while Pete Alonso won't be a-gonezo. It'll be great. The Yankees' braintrust at the meetings will include Brian Cashman and his lieutenants on the ground, though last December, Hal Steinbrenner was famously overseas in Italy as the Arson Judge mess went down.
What could the New York Yankees do at Winter Meetings?
Odds are the Yankees will finalize a deal or two over the course of the Winter Meetings. A few of the big fish should start to land; again, Judge's new contract went down last December, while everyone (sans-Hal) was under one roof. Last year, the location of the Winter Meetings in San Diego allowed Judge to fly in, meet with the hometown Padres and terrify everyone. This time around, with no Nashville franchise (yet), clandestine meetings won't be a similar threat.
Additionally, the Yankees will see some lower-level personnel movement take place.
MLB Draft Lottery
The second annual MLB Draft Lottery will take place on Dec. 5, and due to their subpar record, the Yankees actually have a minute chance of winning the first overall pick. The 0.6% chance is tempting, if unrealistic.
Rule 5 Draft
This year's Rule 5 Draft takes place on Dec. 7, just as the meetings are getting ready to wrap. As always, the Yankees will lose somewhat significant talent here. They protected starter Clayton Beeter and catcher Agustin Ramírez, but several Yankees prospects will be poached and (probably) converted into big-league relievers. Edgar Barclay and Matt Sauer highlight the list of likely losses.
But, remember, if they don't stick on the claiming team's active roster (or Injured List) all season long, they get returned to New York.