What is the role of sympathy in imperial state building? In this essay, inspired by the empiricist philosopher David Hume and the anthropologist Nancy Munn, I develop a materialist concept of sympathy in an effort to cast new light on the expansion of colonial rule. I deploy this concept in an analysis of reports written just before WWII by officials charged with extending the Netherlands Indies government's reach within western New Guinea. Along with gifts and outright acts of coercion, these officials made sympathy into a central component of their practices. Instead of avoiding the natives' gaze, they sought out more or less intimate moments of identification with their subjects; they tried to adopt the Papuans' perspective to reform Papuan ways. In teasing out the causal force of sympathy, as these officials viewed it, I make causal claims of my own about the impact of this experience of empire on the Netherlands' subsequent policy in New Guinea. In doing so, I advocate an approach to anthropological analysis that is empirical, if not empiricist, one that insists on the power of circumstances to shape the imagination, and the power of the imagination to shape the world.