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This article explores the complex relationships between commemoration, history, and financial sponsorship and the resulting representations in our national historical narratives. Upper Canada Village’s Eve of Confederation, written to mark Canada’s sesquicentennial, is ostensibly a love story set in a small town in Confederation-era Ontario. However, a closer look reveals an intricate alliance of stakeholders—governmental, historical, and financial—that influenced the dramaturgy, performance mode, and content of the play. The article examines the play as an example of how the genre of historical performance combined with material conditions that dictate a creative process can appear to subvert, but ultimately reinforce, structures of authority.