In this article, I examine Cavell’s understanding and deployment of the categories of ‘evil’ and the ‘monstrous’ in The Claim of Reason. Arguing that these notions cannot be understood apart from Cavell’s reliance on the notion of an ‘internal relation,’ I trace this notion to its Wittgensteinian roots. Ultimately, I show that Cavell’s view of evil allows us to navigate between two horns of a classic dilemma in thinking about evil: it allows us to see evil as neither a privation nor as a positive force with supra-human potency.