This chapter takes stock of the role that Atlantic exploration and archipelagic imagination played in the utopian literatures of the sixteenth century and the early development of an overseas settler conception of empire. It does so by using Herman Melville’s Moby-Dick (1851) as a critically creative reflection on the intellectual history of law and empire, from Greek and Roman constructions of oceanus as a boundary of juridical space to the crucial role that maritime power would play in the expansion of early modern imperial authority. Of course, that history includes a crucial text for Melville, Thomas Hobbes’ Leviathan (1651). Melville proves to be a critically playful historiographer of the role that the very idea of the law of the sea played in the development of theories of state sovereignty and global commerce, and the historical truth that emerges from his epic summation of that history is that it is discretion in all of its forms, from the crown on down, and not sovereignty as such that is at the center of modern political life, and it is discretion, to pardon or punish, to intervene or not, to save a drowning refugee at sea, or not, that we desperately need to think more about today. If Hobbes and Melville are right, beyond all procedure and institution and any checks and balances, not only the history of law but of justice is inseparable from the irreducibility of discretionary judgment.