William Godwin’s political philosophy positioned him as a key British radical during the French Revolution. And although his popularity was short-lived, his first novel, Things as They Are; or, the Adventures of Caleb Williams, was tremendously successful and influential in the 1790s. The novel illustrates how the humanities can contribute to our understanding of justice, advocating the Romantic virtue of "sympathy" to transform retributive justice to a more restorative and sustainable model, as many current sociologists promote. This article explores the intersection of three facets of the humanities and punishment: A direct engagement with Godwin’s novel Caleb Williams, its relevance to current punishment theory in America, and my own experience with sympathy and punishment in the prison system.