In 2020, Black Lives Matter and other groups brought about another racial reckoning in the United States and across the world. Even a cursory glance at United States history reveals a cyclical nature to racial confrontation, with progress always met with backlash. Why does racial progress follow this cyclic pattern in the United States? Drawing on a comparative case study between the United States and Brazil, this paper uses an historical institutionalist framework to analyze the distinctive constitutional factors that help and hinder racial reckoning in the United States. The paper traces the history of slavery, abolition, key constitutional moments in each country, and their effects on social and economic policies that could promote racial progress. In observing the interactions between these historical events and the institutions that shape their outcomes, this study pinpoints specific structures that help explain the cyclic nature of racial reckonings in the United States. Ultimately, this study finds that racial progress never reaches its full potential in the United States, in part, due to the exploitation of undemocratic constitutional structures, such as federalism and the Senate, that help proponents of racial hierarchy constrain periods of racial progress. In contrast, racial confrontation is stalled in Brazil due to repeated attempts to erase the legacy of slavery whilst maintaining white domination within nearly every constitutional founding.