Winston was born in Minneapolis. He was educated at the Northup School and Folwell Junior High School. California became the family's home in 1959 and in 1962 he graduated from Glendale High. Later he attended San Jose State University and San Francisco State University, which awarded him a bachelor's degree in Semiotics in 1976. Between San Jose State and San Francisco State, he went to sea with the U.S. Seventh Fleet during the Vietnam conflict, serving as a deck-seaman and quartermaster for about 26 months.