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The Cooperative Commonwealth Federation (CCF) was one of the most influential political parties in Canadian History. Without doubt, from a social welfare perspective, the CCF helped Canada build and develop an extensive social welfare system across Canada. The CCF’s major contributions to Canadian social welfare policy during the critical years following the Great Depression has been justly credited to the party. This was especially true during the Second World War when the federal Liberal government of Mackenzie King adroitly borrowed CCF policy planks to remove the harsh edges of capitalism and put Canada on the path to a modern welfare state. Despite the party’s success in shifting the role of the state in society, electoral triumphs proved more difficult for the CCF to obtain. On the federal level, there has been a great deal of discussion about the third-party status of the CCF. One of the objectives of this paper is to indicate that such a role was not pre-ordained for Canada’s democratic socialist group. From 1942 to 1944, it appeared that the CCF was a significant electoral threat to the monopoly of the Conservative and Liberal parties. Ultimately, the party fell short of ending the dominance of the traditional governing bodies. The failure of the CCF to break through with the Canadian voting public is often blamed on the underwhelming performance of the party in the two most populous provinces: Ontario and Quebec. This work explores the efforts put forth by the party to expand the CCF beyond its Western base of support and shows how both provinces were inhospitable to the CCF prior to World War II. In addition, evidence is presented that clearly demonstrates that the CCF in Ontario and Quebec often hindered its own efforts to grow the movement. Horrid organization, non-existent leadership, and serious divisions within the party all helped to contribute to the anemic state of the CCF in Canada’s two largest provinces. These problems were compounded by thinly-veiled racism towards members of the French-Canadian community in Quebec. However, by 1942, the Ontario CCF addressed these issues and became a force to be reckoned with in the province. Attempts were made to incorporate this model into the Quebec branch of the party. The Quebec CCF made some in-roads in expanding their small base on the Island of Montreal. Despite these advances, the party failed to break through in the predominately French-speaking province. The 1945 Ontario and federal elections stemmed the tide of CCF momentum. From that point, the party was relegated to a permanent third-party status at the federal level. In Ontario, the party maintained a substantial degree of public support and would play a role in maintaining the three-party political system in that province. The Quebec CCF could make no such boast. The party’s weak support ensured they would remain on the fringes of Quebec politics during the remainder of the party’s days. While numerous factors are often credited with dooming the CCF in Quebec (opposition from the Roman Catholic Church, the centralizing nature of CCF policy, and media disdain), the available evidence indicates the party failed to address persistent concerns over leadership and organization.