Originally from the Commonwealth of The Bahamas, Winston is a graduate of the New York Institute of Photography and the Art Institute of Ft. Lauderdale. He is also an alumnus of The Catholic University of America, Washington DC, and the University of Miami. He is a former print media and broadcast journalist and a former News Editor at the Broadcasting Corporation of The Bahamas (Nassau). After his last diplomatic appointment as Consul General in 1984, Winston retired from the Bahamas Diplomatic Service in 1993 after almost two decades as one of the pioneering members of the newly created (1973) Bahamian Foreign Service. Winston and his wife now reside in the United States shuttling between South Florida, the District of Columbia (Washington DC) and his birth home in Nassau, The Bahamas.