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Behan lived in a house in Russell Street on the Northside of Dublin which belonged to his mother Christine English, who owned a number of properties in the area. He trained initially as a Jesuit priest (qualifying as a teacher) but shortly before taking vows was found in a compromising position with a young woman; naturally he was required to leave the Jesuit order. Later he joined the Irish Republican Army and became one of Michael Collins' Twelve Apostles, responsible for assassinating British Army officers during the Anglo-Irish War. After the Free State was created, all government workers (teachers included) were required to take an oath of alliegence to the British Crown. Behan's refusal to take such an oath of loyalty resulted in his exclusion from the teaching profession for which he had trained and ultimately a life of comparative hardship.
Behan became a painter and decorator, and married Kathleen Kearney in 1922. Kathleen's Brother Paedar Kearney was a famous song writer and poet (famous for writing the Irish National Anthem 'A Soldier's Song' and 'The Foggy Dew'). Stephen Behan read classic English writers to his children in the evenings before bedtime; Kathleen took their children on literary tours of the city, thus were the seeds of creativity nurtured.