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 first round of the 1981 MLB Draft, Winningham made his Major League debut for the Mets on September 1, 1984. He was once a highly regarded prospect within the Mets organization and was part of the trade that sent Gary Carter to the Mets along with Hubie Brooks, Floyd Youmans, and Mike Fitzgerald.