Edith Wharton composed many dramatic monologues in her lifetime, and from the beginning of her poetic output, her personae tend to speak from a point of extremity between the living and the dead—often choosing, in fact, to narrate the moments of their own deaths. From her 1878 book of juvenilia, in a poem called “The Last Token,” Wharton made her interest in this particular placement evident; she herself, as evidenced by her reading and letters, was often strung between religious and secular modes of life, value, and belief. This article examines two of Wharton's “deathbed monologues” in detail: “The Leper's Funeral and Death,” unpublished in Wharton's lifetime, and—primarily—“Margaret of Cortona,” published in 1901. In each, a person speaks not only at the cusp of their bodily death but also from a vantage point past a symbolic death. In dividing and extending these speakers' deaths in this way, Wharton draws attention to the simultaneous fragility and persistence of the human: between and beyond traditional Christian divisions of body and soul.