This chapter argues that Swift’s darkest satires blur the boundary between irony and earnestness. I suggest that Swift’s satire aims to vex as much through earnest engagement as through confrontation. What is most troubling about Swift’s difficult work is not the contempt, disdain, or disgust for the world he inspires in his readers, but rather the compelling intimacies it sustains with things that are disdainful, disgusting, or otherwise problematic. I examine the points of agreement between Swift’s most famous satires and the work of moral-sense philosopher Francis Hutcheson, showing that, in works like A Modest Proposal and Gulliver’s Travels, Swift does not simply degrade or denude his satiric target, but indulgently hyperbolizes it, raising it to the impossible standard of what Hutcheson calls “disinterested malice.” Hutcheson suggests that this construct, which consists in a deliberate delight in cruelty for its own sake rather than for the sake of any self-interest or gain, is imaginable but not possible. Swift’s satire functions by restoring this ethical potential lost in the actualization.