The MLB offseason is in full swing, and the Winter Meetings are about to put it into overdrive. Front office executives, free agents and their representatives will descend on Orlando, Fla., where chaos will most certainly follow. The futures of stars like Kyle Tucker, Kyle Schwarber and trade targets such as Tarik Skubal are about to come into focus. But what actually happens at the Winter Meetings, and why does one week carry so much offseason weight?
Where are the 2025 MLB Winter Meetings?
The Winter Meetings are taking place in Orlando, Fla., this year. The event requires host cities with large hotel footprints to house 30 team execs, agents, media and league officials in one centralized location. Past locations include Dallas, Texas; Nashville, Tenn.; and San Diego, Calif.
What are the MLB Winter Meetings? Inside a packed schedule
The MLB Winter Meetings are an annual, four-day event held in December where executives from all 30 teams, free agents and their representation all meet face-to-face in the same hotel. You would think some of these meetings could be a phone call, but MLB execs are as old school as they come. When discussing the future of a franchise or a cornerstone talent, a voice memo simply will not do.
Along with free agency and trade rumblings, the following events all take place Dec. 7-10:
- Dec. 7: Contemporary Baseball Era Committee Hall of Fame Vote
- Dec. 9: MLB Draft Lottery
- Dec. 10: Award announcements, including Ford C. Frick award, Scout of the Year and more
- Dec. 10: Rule 5 Draft
That is a lot to pack into just a few days, but MLB finds a way to do so each and every year.
Why the Winter Meetings matter more than any other offseason week
While MLB free agency officially started on Nov. 6, just days after the World Series, plenty has to happen before those free agents can either re-sign, or pick a new team. First, teams have the chance to give out qualifying offers. Second, players must either accept or turn down those qualifying offers. If they choose the latter, they officially become free agents. Third, the MLB GM Meetings were in mid-November, and preliminary discussions at the offseason’s outset typically play a role come early December, when teams are finally ready to build their rosters. Below are the players who accepted their qualifying offers, and thus are not free agents this winter.
| Player | Position | Team |
|---|---|---|
| Trent Grisham | OF | Yankees |
| Gleyber Torres | 2B | Tigers |
| Brandon Woodruff | SP | Brewers |
| Shota Imanaga | SP | Cubs |
Whether it be via free agency, trade or even the Rule 5 Draft, organizations explore every avenue to build out a 40-man roster their executives believe aligns with their 2026 goals. That can’t be accomplished until all of the above happens.
Who actually attends the Winter Meetings?
A great question! The most important characters in this story are the front office executives, who are actually in charge of building a roster for the 2026 season. Agents, free agents and likely trade candidates can also attend the Winter Meetings to make their case to interested parties. The commissioner, along with some owners will at least make an appearance as well.
Of course, I’m leaving out the loudest of the bunch. Reporters, which includes FanSided’s own Robert Murray, will be at the Winter Meetings. This means rumors are sure to fly from the outset, as always, about the best free agents and trade candidates available.
How trades actually happen at the Winter Meetings
Trades don’t always happen at the Winter Meetings, but when they do, it’s thanks to the front office executives in attendance. At times, there is some overlap between agent representing free agents and likely trade candidates. For example, Scott Boras represents both Alex Bregman and Tarik Skubal.
Tigers president of baseball operations Scott Harris will be in attendance, along with New York Mets executive David Stearns. Should the two sides wish to discuss Skubal, or anyone else on their respective rosters, they can do so face-to-face in private. Not to mention, front office pros tend to use reporters to their advantage, floating possible trade candidates to gather public response.
Making a trade at the Winter Meetings isn’t all that tough, assuming both sides are willing.
Why free agency accelerates during Winter Meetings week
Free agency ramps up at the Winter Meetings each and every offseason. Considering agents and even some free agents are in attendance – along with front office executives who might want to sign those players – it shouldn’t come as a huge surprise. By this point in the offseason, the qualifying offer deadline has passed. We know which players are available, but not how much they will cost. That’s accomplished at the Winter Meetings. Here are the best free agents available entering the Winter Meetings.
| Position | Player | Projected AAV |
|---|---|---|
| OF | Kyle Tucker |
$40.2 million |
| SP | Framber Valdez |
$33.3 million |
| OF | Cody Bellinger |
$30.4 million |
| 1B | Pete Alonso |
$28.3 million |
| 3B | Alex Bregman |
$28 million |
| SP | Ranger Suarez |
$26.7 million |
| DH | Kyle Schwarber |
$24.9 million |
| SS | Bo Bichette |
$23.3 million |
| SP | Michael King |
$23 million |
| SP | Tatsuya Imai |
$22.5 million |
| SP | Lucas Giolito |
$20.4 million |
| SP | Zac Gallen |
$18.7 million |
| RP | Edwin Diaz |
$18.3 million |
| RP | Robert Suarez |
$16.8 million |
What a free agent’s market truly is and how many teams are interested is determined in early December. If that’s not the case, said free agent should pursue new representation. Free agency accelerates during the Winter Meetings because every asset that could possibly be needed to make a deal happen is all in one place. Yes, that includes reporters, whose primary currency is information this week in particular.
Trust me when I tell you the chaos is just beginning.
