The MLB Winter Meetings Start This Weekend; What Are They & Why Are They Important?

Major League Baseball often gets bemoaned over the slow burn of its offseason every year. Free agency for the NFL and NBA happens as a flurry of transactions in the span of about a week, whereas baseball takes its sweet time in the four-plus months between its seasons. 

While notable moves still can happen in the first month after the end of the World Series, they’ve become few and far between. But the real meat and potatoes of the winter go down in the first week of December, when the baseball world comes together for its annual Winter Meetings. Interested in more than the Winter Meetings? Check out our comprehensive offseason guide.

What happens?
Above all else, the Winter Meetings should be seen as the biggest networking event for the entire baseball industry. League executives, front-office representatives, managers, free agents, player representation, reporters, and other media entities, and even prospective job seekers, all gather for four days to rub elbows and conduct necessary business. This can include free-agent signings, trades between teams, hiring events, and interviews with national and local outlets.  

Other notable events include the lottery drawing that determines next year’s draft order, scheduled for December 9. The Rule 5 draft, where qualifying players that were not added to a team’s 40-man roster can be selected by another organization that is willing to add them, will take place on December 10. 

These meetings are also an opportunity for Commissioner Rob Manfred and other executives to discuss league-wide issues, including rule changes and impending modifications to the collective bargaining agreement. This will be something for fans to keep an eye on, as the league is implementing the ABS system heading into the 2026 season, which will mark the end of the current CBA. A looming lockout could be a hot talking point at this year’s meetings. 

Another aspect of these gatherings is the onslaught of job seekers looking to find a position in baseball for the 2026 season and beyond. MLB hosts a job fair from December 9-13, and there is a Workforce Development Career Networking Reception on December 8. These events are a way for prospective employees to network with clubs, including their minor league affiliates, to get their names out there for job openings. These fairs require advance registration, and all other Winter Meetings events are closed to the public. 

Notable recent transactions
While they aren’t a certainty by any means, it has become increasingly common for major transactions to take place at these meetings. It’s an easy opportunity for high-end free agents to set the market for premier players in a circuit, and the fact that every organization has representation in one location makes it an easy passage to making trades. 

Here are some notable transactions over the last few years that all took place during their respective Winter Meetings:

• Just last year, the Boston Red Sox swung a trade with the Chicago White Sox for Garrett Crochet. He would go on to finish as the runner-up for the American League Cy Young award. 
• In 2023, the New York Yankees reeled in Juan Soto in a trade with the San Diego Padres. He had another stellar campaign in his contract year and would sign the largest deal in MLB history the following winter. 
• At the 2022 meetings, Justin Verlander agreed to a record-setting two-year contract with the New York Mets for a whopping $86 million guaranteed, with a $35 million option for a third year. On the final day of those meetings, the crosstown Yankees were able to sign superstar Aaron Judge to a nine-year pact worth $360 million (the Giants narrowly missed out on signing Arson Judge a few days earlier).
• The Yankees also made a splash at the 2019 meetings by signing starting pitcher Gerrit Cole to a $324 million deal. It surpassed the previous high-water mark for free-agent starting pitchers, set by Stephen Strasburg ($245 million over seven years to return to the Washington Nationals), signed just days before. 
• The Bronx Bombers also made waves in 2017 (are you noticing a trend?), when they traded for the reigning National League MVP, Giancarlo Stanton, who was only three years into a 13-year pact with the small-market Miami Marlins. 

Expectations for this year’s meetings
This year’s meetings could include some larger free-agent deals, with names like Kyle Tucker, Alex Bregman, and Kyle Schwarber all seeking long-term contracts after strong 2025 campaigns. 

Dylan Cease is already off the market after signing a seven-year, $210 million pact with the Toronto Blue Jays, but he may have set the market for other top arms such as Framber Valdez and Ranger Suarez to follow suit in the coming weeks. 

This year’s free agent class also features some top-tier international talent, with slugging infielders Muneteka Murakami and Kozuma Okamoto expected to land long-term deals, along with starter Tatsuya Imai. Their posting window technically isn’t open until early January, but the Winter meetings could be a prime opportunity for them to secure a deal that meets their expectations. 

Regardless, next week’s meetings will offer an oasis of rumors and headlines in the middle of a long winter where fans can often feel starved for MLB content.

What do you think? What are you hoping to see from this year’s Winter Meetings? Let us hear your predictions in the comments, and as always, stay sweet.