Lawyer
From 1868 to 1874, he worked as a teacher in Grand Pré and Matawan, New Jersey. Seeing no future in teaching, he returned to Nova Scotia in 1874 to article for four years at a Halifax law firm (without a formal university education), and was called to the Nova Scotia Bar in August 1878, placing first in the bar examinations. Borden went to Kentville, Nova Scotia as the junior partner of the Conservative lawyer John P. Chipman. In 1880 he was inducted into the Freemasons - (St Andrew's lodge #1).
In 1882 he was asked by Wallace Graham to move to Halifax and join the Conservative law firm headed by Graham and Charles Hibbert Tupper. Borden became the senior partner in fall 1889 when he was only 35, following the departure of Graham and Tupper for the bench and politics, respectively. His financial future guaranteed, on September 25, 1889, he married Laura Bond (1863–1940), the daughter of a Halifax hardware merchant. They would have no children. (Borden does have descendants, namely Henry Borden, his wife Jean Borden and their children Robert Borden II, Ann Borden, Perry Borden, Mary-Jean Borden and Henry Borden II.) In 1894 he bought a large property and home on the south side of Quinpool Road, which the couple called "Pinehurst". In 1893 Borden successfully argued the first of two cases which he took to the Judicial Committee of the Privy Council. He represented many of the important Halifax businesses, and sat on the boards of Nova Scotian companies including the Bank of Nova Scotia and the Crown Life Insurance Company. President of the Nova Scotia Barristers' Society in 1896, he took the initiative in organizing the founding meetings of the Canadian Bar Association in 1896 in Montreal. By the time he was prevailed upon to enter politics, Borden had what some judged to be the largest legal practice in the Maritime Provinces, and had become a wealthy man.
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