Drafted by the New York Mets in the 1st round of the 1981 Major League Baseball Draft, Winningham made his major league debut with the Mets on September 1, 1984. At one time a highly regarded prospect in the New York Mets chain, he was a part of the Gary Carter trade, along with Hubie Brooks, Floyd Youmans and Mike Fitzgerald.
Drafted by the New York Mets in the 1st round of the 1981 MLB Draft, Winningham made his major league debut with the Mets on September 1, 1984. At one time a highly regarded prospect within the New York Mets organization, he was part of the Gary Carter trade, along with Hubie Brooks, Floyd Youmans and Mike Fitzgerald.