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This thesis explores the nature and challenges of democracy within unions through an historical examination of the emergence and early years of the Canadian Union of Public Employees (CUPE). Formed by a merger of two pre-existing unions in 1963, CUPE casts new light on the Marxist, Michelsian and Institutionalist theoretical approaches to union democracy. The thesis calls into question the narrow and ahistorical link made between centralization, oligarchy and effectiveness on the one hand, and decentralization, democracy and ineffectiveness on the other. Instead, the case of CUPE shows that unions are subject to contradictory pressures and that neither centralization nor decentralization is inherently more democratic. Union democracy is part of an historical process of class formation, in which both union purposes and the boundaries of the democratic community (which can make legitimate claims on members' solidarity and self-discipline) are struggled over. As such, it is possible that decentralizing forces can place narrow and sectionalist priorities over the interests of the broader community. Moreover, the thesis argues that the use of merger as a method of forging greater class unity is itself problematic. The merger which created CUPE involved a protracted struggle over which model of union would prevail. The compromise which was reached entrenched a self-reinforcing cycle of autonomy-seeking by union locals which, over the long term, prevented the development of an effective national union capable of carrying out the democratic will of the membership as a whole. As such, through an historical excavation of the roots of contemporary crises in CUPE, the thesis points to the important way in which the outcomes of past decisions come to structure future political possibilities for unions and other social justice organizations.