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Each year during offseason, Winter Meetings occur, wherein all of the teams' management gathers for discussions on the state of baseball. In OOTP, there are no specific tasks a GM must handle during the Winter Meetings. However, Winter Meetings can have an impact on the game, in the following ways:
- Teams are more likely to initiate trades during Winter Meetings.
- Teams are more likely to respond promptly to trade offers during Winter Meetings.