The meat of the offseason is nearly upon us. On Dec. 7, the baseball world will descend on Orlando, Florida, for the annual Winter Meetings, with agents roaming the hotel halls and general managers going full throttle on the wheeling and dealing. Much of the offseason's business gets done during this weekend, and surely New York Yankees general manager Brian Cashman will be on the prowl.
Free agent signings might get top billing, but the offseason's biggest blockbuster trades often happen during these festivities. For example, it was the 2023 version of the Winter Meetings where the trade that brought Juan Soto to the Bronx was consummated.