Winn was born in Stockton, California and grew up in Clever, Missouri. Winn attended John Brown University in Siloam Springs, Arkansas. On June 8, 1981, he was drafted by the Pittsburgh Pirates in the first round (14th pick overall) of the 1981 amateur draft. Winn made his major league debut on April 10, 1983 with the Pittsburgh Pirates.\n', '

Winn played for the Pirates from 1982 to 1986. On March 27, 1987, he was traded by the Pittsburgh Pirates to the Chicago White Sox for John Cangelosi. He was released by the White Sox during spring training in 1988. He signed with the Minnesota Twins shortly thereafter and finished his major league career with them.\n', '

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