This article explores both recent scholarly receptions of Chaucer’s Pardoner and his reception amongst the Canterbury pilgrims. Contrary to readings which focus on the Pardoner’s “alterity” and outsider status in The Canterbury Tales, the Pardoner is read as occupying a central role in the pilgrims’ social arrangement. By reading the Pardoner in the context of both emerging Lollard debates surrounding institutional abuses in the Church and the orthodox notion of “hypocrisy,” it is shown that the Pardoner’s “con” succeeds precisely because of his institutional safe haven. Finally, the Pardoner’s confidence-game is shown to operate much like the elaborate confidence-game that is Chaucer’s own fiction, opening up discourses of pleasure that allow both author and reader to explore heterodox notions while remaining within an orthodox framework. However, the Pardoner’s hypocrisy also tends toward the erosion of the institutions which allow him to operate his confidence-game.