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Henry Joseph O’Leary was born in Richibucto, New Brunswick, on March 13, 1879 to Henry and Mary O'Leary. He attended the Grammar School at Richibucto for his early education. In 1892 he entered St. Joseph's College and remained there until his graduation in June 1897.
In the fall of 1897 he enrolled in the Seminary of Philosophy at Montreal and entered the Grand Seminary in 1898. He was ordained to the priesthood in 1901 at the age of 22 by Bishop Thomas Barry, Bishop of Chatham.
O'Leary continued his ecclesiastical studies in Rome for the next four years and obtained doctorates in Theology, Canon Law, and Philosophy. During this time he studied French at the Sorbonne in Paris and travelled fairly extensively in Europe and the Holy Land.
Upon returning to Canada in 1905 he was appointed Assistant Priest at Bathurst for a few months and then became Pastor at Jacquet River. In 1907 he was appointed Pastor of the Sacred Heart Parish in Bathurst, and in 1908 he became Vicar General of the Diocese of Chatham.
On May 22, 1913 he was ordained Bishop of Charlottetown, a position he held from 1913 to 1920. On September 7, 1920 Henry Joseph O’Leary was appointed the second Archbishop of the Archdiocese of Edmonton and was installed on December 8, 1920. When O'Leary left the position of Bishop of Charlottetown, his brother Louis was ordained as the next Bishop.
One of O’Leary’s first major acts was the establishment of the Western Catholic in 1921, an Archdiocesan newspaper. Its mandate called for the weekly to report on religious news and to assist people to better understand church teaching.
In addition, an early concern of O'Leary's was to secure priests and seminarians to assist him minister to the large Diocese. In 1922 Archbishop O'Leary went to Toronto in 1922 to speak to the Toronto students of St. Augustine's Seminary and to invite them to come to Edmonton after their ordination to the priesthood.
In 1927 Archbishop O'Leary acquired the buildings of the Oblate Scholasticate and turned it into St. Joseph's Seminary dedicated solely to the formation of diocesan priests. Monsignor James Charles McGuigan became the first Rector of the Seminary before being appointed Archbishop of Regina.
Archbishop O'Leary also oversaw the initial steps in the construction of St. Joseph's Basilica. In 1925 the crypt church was opened for worship, but unfortunately due to financial hardships of the Great Depression it was not completed during his lifetime.
During his episcopate O'Leary oversaw the opening of several new parishes in Edmonton including St. Paul's (1921), St. Alphonsus (1924), St. Andrew's (1927), St. John the Evangelist (1934) and new parishes outside of Edmonton including Edson (1921), Mundare (1922), Bodo (1923), Provost (1925), Killiam (1926), Clandonald (1926), Onaway (1926), Heisler (1927), Olds (1927), Rimbey (1932), Rocky Mountain House (1932) and Thorsby (1934).
On the occasion of his Silver Jubilee of ordination to the priesthood in1926 he was made Assistant at the Pontifical Throne.
Archbishop O'Leary suffered his first severe heart attack at Christmas 1925. John Hugh MacDonald, Bishop of Victoria, was named Co-adjutor of Edmonton with rights of succession of December 12, 1936. Archbishop O'Leary died in St. Joseph's Hospital, in Victoria on March 5, 1938. He was buried in Edmonton.