This dissertation joins recent interrogations of sentiment's racial logic by addressing naughty child-figures who appear in selected U.S. antebellum texts. In Catharine Maria Sedgwick's Hope Leslie, William Apess's Son of the Forest, Nathaniel Hawthorne's The Scarlet Letter, Harriet Beecher Stowe's Uncle Tom's Cabin, and Harriet Wilson's Our Nig, these children resist adult attempts to make them adhere to disciplinary regimes of domesticity, literacy, and Christian conversion. Child-figures are used by white authors to articulate often unconscious racial views and by writers of color to expose U.S. racism. I argue that the particular blend of sentimental pathos and minstrel entertainment made naughty childhood a vehicle for articulating tentative, and often deeply problematic, sympathy between whites and people of color from Indian Removal until abolition. Chapter One, "Manifest Sympathy: Indian Removal and Childhood Naughtiness in Catharine Maria Sedgwick's Hope Leslie and William Apess's A Son of the Forest," depicts the naughty child's entrance onto the sentimental stage in the 1820s as authors explore Jacksonian "Indian-hating" from a child's point of view. Chapter Two, "Misreading The Scarlet Letter: Racial Masquerade and Hawthorne's Naughty Child," maintains that Hawthorne depicts his naughty white girl, Pearl, in terms that invoke both Indian dispossession and African-American enslavement. In Chapter Three, "Mixed Feelings: Naughty Children and the Limits of Sentimental Discipline in Uncle Tom's Cabin," I argue that Stowe's Topsy demonstrates sentimental reliance on a minstrel aesthetic to supplement contradictory racial "sympathies." Finally, in Chapter Four, "Naughty Girl/'Knotty Queries': Interrogating Sentimental Racism in Harriet Wilson's Our Nig," I discuss Harriet Wilson's sharp rebuke to sentimental racism as a naughty black child suffers so palpably that the novel's white sentimentalists become apologists for sadism. After the Civil War, literary naughty children relocate from the heart of domestic space to the frontiers of empire. My project finds that by containing interracial sympathies to youth and converting concern for people of color into concern for white children, the interracial alliances imagined in these texts never came of age.