In The Rhetoric Aristotle tells us that a judge who allows pity to influence his decision making is about as good as a carpenter who uses a warped ruler. He goes on, however, to give detailed advice to advocates about how to evoke pity in the judge. Thus Aristotle treated compassion in its relation to justice as both unlawful and inevitable. Contemporary legal theory, by contrast, tends to take an all or nothing-view of the relation between compassion and justice. Some argue that compassion should guide our deliberations about justice. Others maintain that we must protect our judgments about justice from the distortions of compassion. In this paper I contemplate the middle ground – and perhaps even the paradox – found in Aristotle’s discussion: that compassion in its relation to justice is and must be both essential and illicit.