Gerard Anthony Francis Conroy was born in Dublin to John (Jack) and Esther Conroy, and was one of ten siblings: Alphonsus (Ollie), Laurence (Lar), John (Donny), Rita, Peter, Michael, Vincent, Paul, and Marie. Christened as Gerard, he soon became known by the name Terry as he could not pronounce 'Gerard' as a young child. His mother held two jobs: as a factory worker and an office cleaner. The family lived in the suburb of Cabra, and had very limited finances. Being one of the younger children he was indulged, and took advantage of his lack of household chores to spend the majority of his time playing football in the street. However he was arrested by a plain-clothed policeman and sentenced to probation in Children's Court for playing football in the street. He later credited his ball control skills to the many years he spent playing football with large numbers of other children in the tight streets of Cabra. His father and brothers were in the printing trade, and his brother Ollie, a talented footballer, rejected the opportunity to turn professional at Wolverhampton Wanderers in 1950 in order to remain employed in Dublin as a machine minder and play football part-time in the League of Ireland. Three more of his brothers also played in the League of Ireland, and both Ollie and Michael played in the Shelbourne team that won the FAI Cup in 1960.