Early Life
O'Callaghan was born on 26 January 1954 into a republican family in Tralee, County Kerry. His paternal grandfather had taken the Anti-Treaty side during the Irish Civil War. O'Callaghan's father, who had served in the IRA, had been interned during World War II at the Curragh Camp, in County Kildare.
By the late 1960s, the teenaged O'Callaghan had ceased practicing the Catholic religion, regarding himself as an atheist and a Marxist. Therefore, he sympathised with the Northern Ireland Civil Rights Movement. In 1969, violent attacks took place targeting civil rights organizers and many other Catholics. Believing that he would be helping to combat British imperialism, O'Callaghan volunteered for the newly founded Provisional IRA. He was 16 years-old at the time.
Soon afterwards, O'Callaghan was arrested by local Gardai after he accidentally detonated a small amount of explosives, which caused damage to his parents' house and those of his neighbours. After demanding, and receiving, treatment as a political prisoner, O'Callaghan quietly served his sentence in the Irish prison system.
After becoming a full-time volunteer, O'Callaghan was involved in various IRA operations, notably in May 1974 a mortar attack on a British army base at Clogher, County Tyrone in which a female "Greenfinch" Ulster Defence Regiment (UDR) soldier, Private Eva Martin, was killed. In his memoirs, O'Callaghan wrote that, although some individual UDR soldiers had had links to loyalist paramilitary gangs, he subsequently learned that Private Martin was not one of them. A high school teacher, she and her husband had both volunteered for the UDR. It was Private Martin's husband who found her body on a shattered staircase inside the base.
In August 1974, O'Callagan walked into a bar in Omagh, County Tyrone and fatally shot Detective Inspector Peter Flanagan of the Royal Ulster Constabulary's Special Branch. D.I. Flanagan, a Catholic, was regarded as a traitor by both the IRA and many local residents. D.I. Flanagan was also rumoured, falsely, to have used excessive force while interrogating IRA suspects.
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