The New York Yankees, in their illustrious 107-year history, have made quite a few big-time purchases and trades. The biggest was the worst for the Boston Red Sox when their owner being money short for his other endeavors sold Babe Ruth to the New York Yankees, and we all know how that turned out. But in recent years, the Yankees have made some pretty impressive deals in the Winter Meetings. The first one was technically not during the meetings but a few days before at Dallas, Texas.
Mike Mussina (2000):
Just a few days before the Winter Meetings, The New York Yankees signed the Baltimore Orioles Mike Mussina.