To understand the persistence of racial disparities in the United States, inequality scholars have increasingly focused attention on historic regimes of violence and social control. In particular, a burgeoning literature examines the legacy of slavery, generally finding that where slavery was deeply entrenched, today racial inequalities and African-American deprivation are more acute. However, taking seriously the notion that history matters means considering not only the lingering effects of dehumanizing social control institutions like slavery but also the ramifications of antebellum institutions and cultures of resistance and resilience African Americans built for survival. Using quantitative methods, I examine the relationship between antebellum free African-American populations and racial inequalities in modern state-sanctioned social control. Focusing on the understudied Northeast, a region where free African-American communities flourished despite coexisting with slavery, I find that where free African Americans were more prevalent—and, thus, resistance to White’s social control efforts and resilience in the face of White hostility more robust—those same areas today display reduced levels of racial inequality in social control (i.e., lower Black–White arrest rate disparities) and reduced absolute levels of minority social control (i.e., lower African-American arrest rates). Mediation analyses reveal contemporary civil rights infrastructure, Black congregations, and Black political power operate as structural safeguards and are important components of the legacies of resistance and resilience left by free African Americans.