The son of a preacher, Winston was born in 1957, in the hills of Manchester parish, near Christiana, in Jamaica. His parents were very fond of music and it was only natural for him to sing in church. After his father died in 1971, Winston left his native home and moved to Kingston, where his sister was a teacher. In this new city environment, he became friend with Hugh Mundell, Earl Sixteen and Wayne Wade. Because he was sure of their talent, he went with them to their first auditions and even wrote some of their first songs, like Earl Sixteen's "Malcolm X", later taken up by Dennis Brown.

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