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

Craig Breslow, the Boston Red Sox's new President of Baseball Operations, should be gearing up for his first foray into the gauntlet that is the annual Winter Meetings.

Craig Breslow
Craig Breslow / Billie Weiss/Boston Red Sox/GettyImages
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Craig Breslow, the Boston Red Sox's new President of Baseball Operations, should be gearing up for his first foray into the gauntlet that is annual Winter Meetings. There are lot of questions that will need to be answered in Nashville.

Will the Red Sox make history and sign Shohei Ohtani? Will they remember to focus some of their attention on their struggling rotation? Could they defy the rules of probability and draw the first position in next year's draft lottery? Here are the basics of the Giants' trip to the Winter Meetings this year.

What are the Winter Meetings?

The Winter Meetings are the crown jewel of MLB's offseason, a four-day gathering of representatives from all 30 teams who assemble to negotiate with each other, as well as with free agents and their representation. Some of the biggest, most notable contracts and trades in MLB history take place at the Winter Meetings; for the Red Sox, their most famous might be the $160 million contract they gave Manny Ramirez in the 2000 offseason. This year, Winter Meetings will be held from Dec. 3 - 6 in Nashville, Tenn.

What could the Red Sox do at Winter Meetings?

Other than being one of the many teams dealing with the elephant in the room, Shohei Ohtani, who has been more seriously connected to the Red Sox in recent weeks, Boston should turn their attention to rotation additions during the Winter Meetings. Given that they're down to four starting pitchers, that list is helmed by the fragile-as-glass Chris Sale, and the others are still relative newbies, the Red Sox could really use some veteran pitching.

Luckily, veteran pitching makes up a good deal of the top of this year's free agent class; Jordan Montgomery, Blake Snell, and Aaron Nola are all available as the most expensive options, but perhaps cheaper options in Twins highlight Sonny Gray, former Red Sock Eduardo Rodriguez, and a possible fixer-upper with historical greatness in Lucas Giolito could also be considered.

Then, there's the question of Alex Verdugo, whose departure from the team has been hinted for weeks. There's a chance the Red Sox might deal with the Yankees in order to fill Boston's opening at second and New York's opening in the outfield, or maybe even with Cincinatti for Reds trade piece Jonathan India.

Rule 5 draft

The Rule 5 draft, made up of minor leaguers with 4-5 years of service time, takes place during the Winter Meetings. Only teams without a full 40-man roster participate; as of writing, the Red Sox have one open spot after moving Nos. 9 and 10 prospects Wikelman Gonzalez and Luis Perales to the 40-man roster 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 Red Sox have a 1.2% chance of drawing first position. They picked 14th in the 2023 draft, but will probably move up a few places next year.

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