Herman Melville’s final novel The Confidence-Man destabilizes conventional Western models of ethical behavior, particularly Kantian notions of moral agency, by exposing and challenging their basis in rationality and a progressivist model of history. The Confidence-Man shows rationality to be nothing more than one way, among many other possible ways, that human beings attempt to fix the world in their understanding and justify their moral choices. I use these insights from The Confidence-Man to illuminate Melville’s opposition to the missionaries’ work of civilizing and Christianizing the South Seas islanders in his earlier travelogues. In Typee, his first novel, Melville demonstrates that layers of existence—in fact, real human lives—are denied when the story of human relations is framed as a narrative of progress. This thesis concludes by proposing that Melville reworks the idea of failure as a potential strategy against the totalizing narrative of advancing rationalism.