What are the Winter Meetings and what deals could the White Sox get done there?

More than perhaps any other team in baseball, the Chicago White Sox have a lot to do. This year, they finished with their worst win record since 1931 and underwent a string of bad publicity that included their shortstop getting rocked and a mutiny of players, current and former, that revealed the clubhouse culture to be toxic. But, hey, the 2023 season is gone and past, and the only thing left to do is to build off of mistakes. The Winter Meetings are coming up, and even if the White Sox won't be the most major players, there's a lot they can and need to do to put a team on the field next season. Here are the basics of their trip to Nashville this December.

What are the Winter Meetings?

The Winter Meetings are an annual conference of Major League Baseball's owners, executives, managers, agents, and so on who come together to negotiate trades, sign free agents, and generally get their teams into more solid shape ahead of the coming season. These meetings are the centerpiece of every offseason, where most of the biggest trades and signings take place. Last year, the White Sox didn’t make much of a splash in terms of transactions, but this year they’re expected to be very much open to trades. This year, Winter Meetings will be held from Dec. 3 - 6 in Nashville, TN.

What could the White Sox do at Winter Meetings?

The White Sox have made it clear that they'll entertain trades for almost every single player on their roster, including ace Dylan Cease and slugger Eloy Jimenez. They already traded away reliever Aaron Bummer for five Braves, and chatter surrounding Cease is substantial. Given that the White Sox are working toward a total rebuild, to break down the organization and built it back from the ground up, It's harder to say what the White Sox aren't interested in this offseason than what they are.

Yasmani Grandal, Liam Hendricks, Mike Clevinger, Tim Anderson, and Elvis Andrus — just to name a few — are all free agents who are not expected to return, which puts Chicago out of a catcher, a reliever, a starter, and two middle infielders. Trying to pinpoint a place to start a rebuild isn't exactly an easy task, but if they do lose Cease and Clevinger, the White Sox will at the very least need pitchers that can go long into games. At the moment, they have no depth options at second base or shortstop, so those will also be two areas of major concern.

Rule 5 draft

The Rule 5 draft, made up of minor leaguers with 4-5 years of service time, also takes place during the Winter Meetings. Only teams without a full 40-man roster participate; as of writing, the White Sox’s 40-man is full after they moved Nos. 5 and 10 prospects, Jake Eder and Cristian Mena, onto it to protect them from the draft.

MLB Draft lottery

The second MLB Draft lottery, wherein the 18 non-playoff teams will draw to determine draft order in 2024, will also take place during Winter Meetings. The White Sox have a 14.7% chance of drawing first position, the highest behind the Athletics, Royals, and Rockies.