The piece notes Roger Maris’s move to the Yankees in December 1959 as a precursor to his iconic 61-homer MVP season that followed the trade.

Overall, the article blends historical context and player impact to justify ranking these winter meetings trades among the most significant in history.

An honorable-mentions section highlights several historic winter meetings trades with dates and players, underscoring the breadth of their impact.

Roberto Alomar and Joe Carter’s December 1990 deal to the Blue Jays helped power their back-to-back World Series titles in the early 1990s.

Chris Sale’s December 2016 move to the Red Sox is noted for the strong prospect haul and his subsequent performance.

Adam Wainwright’s December 2003 swap to the Cardinals, in exchange for J.D. Drew, is discussed for its long-term durability impact.

The ranked list opens with Johan Santana’s December 1999 pickup by the Twins, a Rule 5 acquisition that helped him become an ace and Cy Young winner.

A December 2009 three-team trade brought Max Scherzer to Detroit, Curtis Granderson to the Yankees, and Edwin Jackson/Ian Kennedy to the other clubs, illustrating broad, lasting influence.

Miguel Cabrera’s December 2007 move to the Tigers is highlighted for elite production and the noteworthy return package the Marlins received.

Joe Morgan’s late-November 1971 arrival to the Reds signaled a turning point, with Morgan becoming a top player and fueling Reds’ peak years.

Gary Carter’s December 1984 transfer to the Mets is discussed for his impact leading to the 1986 World Series run.

Frank Robinson’s December 1965 trade to the Orioles is cited for its historic reputation as a poor deal for the Reds despite Robinson’s stellar output.

The article situates 2025 as the current context, referencing recent moves like Juan Soto to the Mets and Garrett Crochet’s trade to the Red Sox from 2024.