This chapter examines the expressions of mockery, disdain, and contempt that lace the otherwise brilliant diagnosis of despair that is delivered by Anti-Climacus in Part One of The Sickness Unto Death (1849). Clearly favouring the third-personal (external/objective) perspective from which he launches his “Christian psychological exposition,” Anti-Climacus sees fit to invalidate the first-personal (internal/experiential) accounts reported by the disadvantaged selves whom he diagnoses. While it is possible that Anti-Climacus amplifies his disdain in order to accelerate the “upbuilding and awakening” of selves in despair, I suggest that there is more going on in The Sickness Unto Death than is typically discussed by scholars and commentators. My particular focus in this chapter is the despair enacted by Anti-Climacus himself, which, I offer, accounts for his failure to attend more charitably (and Christianly) to the despairing selves whom he diagnoses. Owing to the indirect efforts of his wily editor, one S. Kierkegaard, Anti-Climacus appears in the text as both an astute diagnostician and an exemplary sinner. By dint of his unwitting service in this latter capacity, Anti-Climacus reminds his readers of their moral obligation to provide companionship and compassionate witness to selves in despair. Although it is true that selves in despair must work out the terms of their own salvation, they need not suffer in isolation, and they should not be expected to endure the compound suffering heaped upon them by those who, like Anti-Climacus, blame them for failing to become the selves they are meant to be.