This paper considers the discursive strategies deployed in Olivia Chow’s 2014 Toronto mayoral concession speech in comparison to those of the Letter to Canadians penned by Jack Layton in 2011, and the resulting influence on her electoral trajectory as a pol. Layton’s letter was published shortly after the New Democratic Party’s (NDP) Federal electoral surge to Official Opposition status, a first for the far-Left party in Canadian history, and would serve as an New Democratic ideological keystone. Chow’s rhetoric invoked Layton’s words and the historical circumstances of their authorship. This project explores the relationship between public address and political epistolary traditions, and the narrative bond they create between author and speaker, and reader and audience. Most specifically it considers how an intertextuality between Chow and Layton’s documents contribute to political ethos and the greater progressive ideological narrative to which they both belong. Theorists discussed in substantial measure include Allen (2000), Corcoran (1994), Hall (2009), Neville-Shepard (2014), Parrish (1954), Rabinowitz (1987), and Weaver (1982).