[1] Healy was born on St. Patrick's day 1872, in Drogheda, County Louth, the son of a solicitor James Stanislaus Healy and his mother Kate Mary Appleyard[2] was the daughter of a Church of Ireland clergyman.
Educated in Drogheda Grammar School and Trinity College Dublin he graduated with a degree in Literature and Classics, winning prizes while at college.
He studied law and was called to the bar in 1906[3] although never practiced.
Healy was a staunch Unionist,[5] had shots were fired at his home during the War of Independence, he defended the Unionist cause in his writings in the Irish Times as his obituary in The Times of London it was noted that, he was the protagonist of a losing cause.
Healy married Adeline Alton in 1898 and had two sons.