Political Career
Woolf was elected to the Legislative Assembly of the Northwest Territories in the 1902 election, defeating Heber Simeon Allen in the district of Cardston. He served in this capacity until 1905, when the new province of Alberta was created out of part of the Northwest Territories. Though in keeping with territorial custom Woolf had served as an independent in the territorial legislature, federally he was a Liberal, and in the debate over whether Alberta's politics should be conducted on an independent basis or along party lines, he was a strong advocate of the latter option.
His side prevailed, and when he ran for the Legislative Assembly of Alberta in the province's inaugural provincial election, it was as a provincial Liberal. He defeated Conservative John F. Parish with the largest majority of any candidate in southern Alberta to win the new provincial district of Cardston. Historian L. G. Thomas attributes this margin to Woolf's having "the Mormon vote in pocket". In the 1909 election, he was re-elected by a reduced margin over Conservative Levi Harker.
During 1910's Alberta and Great Waterways Railway scandal, Woolf remained loyal to Liberal Premier Alexander Cameron Rutherford. He was rumoured to be Rutherford's choice to succeed Public Works Minister William Henry Cushing, whose resignation had precipitated the scandal, but Rutherford's government collapsed before he appointed any successor. When Rutherford was replaced by Arthur Sifton, Woolf supported the new government, even though its approach to the Alberta and Great Waterways question was opposed to Rutherford's, which Woolf had also supported.
In 1910, Woolf bought a house in Salt Lake City in preparation for a return to Utah. His son believed that this was due to the activities of a Protestant minister in Cardston who was investigating and bringing to the attention of the authorities violations of Canada's anti-polygamy laws. Beginning in late 1911, he was absent from the legislature, and in 1912 he resigned and returned permanently to the United States. The ensuing by-election returned his brother, Martin Woolf, as his replacement.
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