Henry James's The Princess Casamassima is, among other things, a novel about becoming a terrorist. What kind of past suits one to a terrorist's work? What makes this especially interesting is the fact that the novel's main character, Hyacinth Robinson, is offered as both the most and the least likely of practical anarchists; he is small, handsome, vaguely literary, and not at all violent. What seems most to make Hyacinth a good terrorist is the fact that he is not just good (clever, sensitive, etc.), but perfect; he is said by other characters “never to make a mistake.” If The Princess is about making good terrorists out of perfect gentlemen, it is also about making characters make sense within the classic realist novel. Indeed, in his preface, James understands Hyacinth to be an exemplary case of his thinking about character. This essay argues that James offers a productive analogy between making characters and making trouble that undermines the stories we tend to tell about the novel and its subjects.