Early Life
Gregory was born in Ballybough in Dublin's Northside, the second child of Anthony Gregory and Ellen Gregory (née Judge). His mother, born in 1904 in Croghan, County Offaly, moved to Dublin to work as a waitress while his father, born in North Strand Dublin, worked as a warehouseman in Dublin Port. The family originally lived in a one room apartment on Charleville Street. The family applied for housing by Dublin Corporation but were denied with an official saying "come back when you have six ". The incident left an impression on Gregory and he would refer to it in interviews later in life. The family were able to later move to a house on Sackville Gardens near the Royal Canal using money they had saved. Gregory won a Dublin Corporation scholarship to Christian Brothers at O'Connell School. He later went on to University College Dublin (UCD), where he received a Bachelor of Arts degree and later a Higher Diploma in Education, funding his degree from summer work at Wall's Ice Cream Factory in Acton, London. Initially working at CBS Synge Street, Gregory later taught at Coláiste Eoin, an Irish language secondary school in Booterstown, where he taught History and French. A number of his students, both at Synge Street and Coláiste Eoin included the future politicians John Crown, Colm Mac Eochaidh, Aengus Ó Snodaigh, the comedian Dara Ó Briain, and musician Liam Ó Maonlaí.
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