 Winters was drafted by the New York Yankees in the first round of the 1978 amateur draft, and spent most of his career in the minor leagues.He was released by the Yankees in 1985, and signed with the Chicago White Sox, before being returned to the Yankees in a trade for cash and several minor league players.He signed with the Kansas City Royals in 1987, and made his major league debut in 1989 with the Royals.