The Winter Meetings are the annual baseball event where the offseason heats up with trades, free-agent signings, and buzzing rumors. Held over four days in Orlando, these meetings mark the most active period of the offseason, often featuring the biggest player moves.
To get ready for this year’s event, here are ten key questions to consider:
1. Will Kyle Tucker sign a new contract? Despite being the top free agent, it’s common for the leading player to remain unsigned before the meetings. Tucker has attracted attention from major teams like the , Mets, and Yankees. If he moves, the Cardinals might target Cody Bellinger, another strong outfielder, as a backup plan. Usually, top free agents secure deals during the winter meetings, so Tucker’s signing might be imminent.
2. Will the Cardinals trade Nolan Arenado? This seems likely, especially after the club paid $20 million to move Sonny Gray recently. Arenado wants a trade to a contender and holds a no-trade clause, but his trade options might be limited. While other players like Alex Bregman and Eugenio Suarez are free agents and arguably stronger, a highly subsidized Arenado contract could appeal to some teams.
3. Will surprise trade candidates appear? Every offseason, a few unexpected players become available. Last year, the Astros’ Tucker trade was unforeseen, and the Chris Sale trade was a shock two years ago. This year will likely reveal new surprising trade possibilities, even if the actual deals happen after the meetings.
4. Will the pitcher market keep moving? The pitching trade scene is already active, with recent trades like Gray to the Red Sox and Dylan Stop’s big contract with the Blue Jays. Plenty of quality free agents and trade candidates remain, so more pitching moves are certain during and after the meetings.
5. Will any star players from Japan’s NPB sign with MLB teams? Top talents like right-hander Tatsuya Imai, third baseman Munetaka Murakami, and first baseman Kazuma Okamoto are eligible and have a limited signing window. They can be signed any time during the offseason, including the Winter Meetings.
6. Will any notable players re-sign with their current teams? It’s common for some free agents to return to their existing clubs after exploring options, such as Alex Bregman with the Red Sox or Bo Bichette with the Blue Jays. While meetings typically highlight player moves, some stars choose stability.
7. Are there updates on manager interviews? All 30 MLB managers will address the media during the meetings. Although many comments might be routine, these sessions can reveal important updates about player roles, injuries, and team changes.
8. Will new members be inducted into the Hall of Fame? The Modern Era Committee will vote on eight nominees like Barry Bonds and Roger Clemens, with results announced in Orlando. A candidate needs 12 out of 16 votes to enter the Hall.
9. Who will win the draft lottery? To discourage tanking, MLB holds a lottery for the top six draft picks among non-playoff teams. The worst records increase chances, and recent years have seen teams leapfrog others to secure top picks.
10. Will a hidden gem be found in the Rule 5 Draft? Last year’s White Sox selection Shane Smith became an All-Star rookie, showing the draft’s potential impact. Rule 5 picks must stay on MLB rosters the next season or return to their original team, offering fresh opportunities for overlooked players.
Fan Take: The Winter Meetings serve as a pivotal moment shaping the baseball landscape for the upcoming season. Fans should pay close attention as the decisions made here often dictate team fortunes and excite fanbases with major signings and trades that keep the sport dynamic and intriguing.

