Barillaro was born in Italy and moved to Canada with his family at a young age. In 1978 he had his first conviction for heroin trafficking. In 1980 he was out on parole but was arrested again shortly after for selling heroin to an undercover policeman and was sentenced to another 3 years. Barillaro was also involved in loansharking and bookmaking, mainly in the Niagra Falls area. He became closely affiliated with Ontario gangster John Papalia and became a member of the Magaddino family in Buffalo, New York.