Plato’s Socrates argues that ethics is a matter of right thinking, whereas Charles Kingsley says, “Be good, sweet maid, and let who will be clever.” If behaving virtuously is interdependent on thinking rationally and well, then it would seem that being virtuous ought to be a major support for making good judgments, including one’s judgments of other people. On the other hand, the idea of innocence is often seen as suggesting that good people are not very bright in judging the rest of us: the Angel in the House is no match for the Machiavel. A number of Shakespeare’s plays show people misjudging other people, and one of the subtlest and most powerful of those plays is Othello. Naturally other elements like age, experience, similarity of background, time spent together, and luck play a role in how reliable people’s judgments of one another are, but looking carefully at how they judge one another and where they go wrong may help us to choose between Plato’s approach and that of John Henry Newman’s opponent, the author of Water Babies. We usually divide virtues into the intellectual and the moral, and pretty obviously having the former would increase the likelihood of making a rational judgment that is more probably true, so the real issue is whether moral virtue contributes to judging people well, perhaps contributing through the interpretive imagination. Does it seem that the virtuous characters in Othello are more or less likely to misjudge others, and how does their virtue shape their judgments?