The events of the Easter Rising have been subjected to extensive analysis by historians who have focused on military strategy as a means of explaining the occupation of specific sites. However, Jacob’s Biscuit Factory and the South Dublin Union have proven resistant to this paradigm. The political value of both places can be understood by giving close attention to the long history of antagonism between these two institutions and the Irish Transport and General Workers’ Union, out of which the Irish Citizen Army that fought in the rising was formed. In his articles for the Irish Worker and Workers’ Republic, James Connolly adapted traditional republican discourse of economic emancipation through political sovereignty to address a contemporary urban context. An understanding of the way that this discourse functioned facilitates an understanding of the role of Jacob’s Biscuit Factory and the South Dublin Union in the Easter Rising: as sites of actual and symbolic liberation. This analysis of popular discourse in the contemporary press offers a new approach to the study of events that have been termed the Irish Revolution, and it presents a model for understanding the way that republican discourse accommodated the very different political objectives of Irish separatists.