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Haultain was born in England on November 25, 1857. When he was young his family moved to Canada and he spent his childhood in Montreal and Toronto. He received a bachelor's degree from the University of Toronto in 1879, and then trained to be a lawyer. In 1884 he moved to Fort Macleod in the Northwest Territories and set up his own law office. Shortly after arriving there he got involved in politics as a member of the Council of the Northwest Territories, and later as a member of the Legislative Assembly.
Haultain wanted the Territories to have responsible government. He also wanted the Territories to gain more political power so they would have greater control over their future. He tried to convince the federal government to create a single province out of the Territories. The Canadian government created the two provinces of Alberta and Saskatchewan on September 1, 1905.
Haultain was not made premier of either of the two new provinces because he did not get along with the Prime Minister. He was leader of the Opposition of Saskatchewan from 1905-1912, and then was made chief justice of the Superior Court of Saskatchewan. In 1916 he was knighted and also became chancellor of the University of Saskatchewan. He retired in 1938, and died on January 30, 1942.