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

The Milwaukee Brewers have been in a surprising spot this offseason: toward the center of the attention. With the shock departure of manager Craig Counsell to the division rival Cubs and unceremonious non-tendering of Brandon Woodruff following a surgery, eyes have been on the Brewers in a big way. With Winter Meetings just around the corner and a lot of spots they still need to fill in their roster before the 2024 season, could they be setting themselves up to make some big moves? Here are the basics of the Brewers' trip to the Winter Meetings this year.

What are the Winter Meetings?

The Winter Meetings are an annual gathering 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 shapes ahead of the coming season. These meetings are the centerpiece of every offseason, where most of the offseason's climactic signings and trades take place. The Brewers had a relatively quiet presence at the meetings last year, as they weren't in on big name signings like Aaron Judge and Trea Turner and didn't make any significant signings. This year, Winter Meetings will be held from Dec. 3 - 6 in Nashville, TN.

What could the Brewers do at Winter Meetings?

After the surprising non-tendering of Brandon Woodruff ahead of the deadline, the Brewers will be looking out for starting pitching to round out their rotation. This is a common theme this offseason; the free agent class is overwhelmed with starters, so a lot of teams are in need of them. There are whispers that Corbin Burnes will be traded away, effectively gutting Milwaukee's top pitching talent after Woodruff's dumping, so the Brewers will be keeping their eyes open for one or two starters, at least, and could very well fill some roster spots at Winter Meetings.

DH Rowdy Tellez being non-tendered was less of a surprise, but it does means the Brewers are looking for a new designated hitter. Christian Yelich and William Contreras have both spent time at DH, but Contreras is currently the only catcher on the Brewers' roster (aside from prospect Jeferson Quero, who was moved to the 40-man to be protected from the Rule 5 draft and will be reassigned to the minors following the draft), and Yelich has left field more than locked up. Tellez, despite a serious decline in 2023, was at one point capable of a 30+ home run season, so the Brewers will be looking for a DH who can perform with similar power.

Third base will also be a concern, as the Brewers lost Josh Donaldson to free agency, released Brian Anderson earlier this year, and seem unlikely to give Andruw Monasterio the everyday role. Aside from that, most of their core seems to be taking shape, especially with the new addition of former Yankee Jake Bauers at first base.

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 Brewers still have five open spots after moving Nos. 2, 17, and 23 prospects Jeferson Quero (who is also MLB Pipeline's No. 32 prospect overall), Bradley Blalock, and Oliver Dunn to the 40-man 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. As a playoff team, the Brewers position is already set at 20th, down two places from this year's draft.