He worked his way through with a job as assistant in the library and participated in debating and moot court activities. When James Lougheed needed a junior for his Calgary, Alberta law office, Bennett was recommended by the dean, Dr. Richard Chapman Weldon. Bennett was then a partner in the Chatham, New Brunswick, law firm of Tweedie and Bennett. Max Aitken (later to become Lord Beaverbrook) was his office boy. Aitken persuaded Bennett to run for alderman in the first Town Council of Chatham. Aitken managed Bennett's campaign and Bennett was elected by 19 votes out of 691 cast. Political, law, and business success (1897–1911) Despite his election to the Chatham Town Council, Bennett's days in the town were numbered. In 1897, he moved to Calgary, North-West Territories. He negotiated to become the law partner of James Lougheed, Calgary's richest man and most successful lawyer. By 1905, Bennett was buying and selling land and was successful at it due to the law firm's retainer being the Canadian Pacific Railway. Bennett also invested in the oil company, Calgary Petroleum Products Company, and became director and solicitor. He also worked with Aitken to produce the Alberta Pacific Grain Company, Canada Cement, and Calgary Power. Bennett's reputation grew. Bennett described himself as a teetotaler (although he was known to occasionally drink alcohol when the press was not around). Bennett was elected to the Legislative Assembly of the North-West Territories in the 1898 general election, representing the riding of West Calgary. Aitken managed this campaign too. Bennett was re-elected to a second term in office in 1902 as an Independent in the North-West Territories legislature. He gained the nickname "Bonfire Bennett" due to his extemporaneous, quick, and persuasive speaking manner. In 1905, when Alberta was carved out of the Territories and made a province, Bennett became the first leader of the Alberta Conservative Party, though lost in a landslide in that year's election to the Liberals. In 1909, he won a seat in the provincial legislature. In 1908 Bennett was one of five people appointed to the first Library Board for the city of Calgary and was instrumental in establishing the Calgary Public Library. In 1910, Bennett became a director of Calgary Power Ltd. (now formally TransAlta Corporation) and just a year later he became president. His leadership projects completed included the first storage reservoir at Lake Minnewanka, a second transmission line to Calgary,