Portraits of sympathizers recur across American literature, from nineteenth-century narratives by Edward Everett Hale Jr., Loreta Velazquez, and Walt Whitman to Viet Thanh Nguyen's twenty-first-century novel. Together, their texts elucidate why this understudied trope remains provocative. Whereas nineteenth-century literature often imagines how sympathy fosters national cohesion, feeling for the enemy threatens such stability and prompts government efforts to regulate sentiment. Sympathizers may perform loyalty to claim the authority associated with white masculinity. Yet they also gain power by confessing to criminal sentiments. This figure thus embodies fantasies of rebellion, fears of national dissolution, and the state's affective power.