The current paper revisits Anthony Trollope's Victorian novel, The Way We Live Now, focusing on the main character of Augustus Melmotte. The paper analyzes the novel and its literary figure of a corrupt financier or swindler, drawing out theoretical and pedagogical contributions for organizational and management research. Contributions are framed in terms of imaginative organizational role archetypes embodied in swindler characterizations, swindlers' institutional work across societal elites, and the dark sides and grey areas associated with swindlers' organizational and financial misconduct. The rise and fall of Augustus Melmotte in Trollope's Victorian English society thus finds its cultural parallels today in outsiders who challenge financial and political elites and the status quo, at high personal risk to themselves and others complicit in their schemes. The important organizational conclusions concern the importance of recognizing dynamic figures that seize immense power over organizational, financial and political cultures.