This chapter examines ideological underpinnings of the Spanish–Indian binary in Mexican and Mexican American indigenism and mestizaje. In a reassessment of Chicanx literary history, it looks at the life and writings of sixteenth-century Dominican cleric, Bartolomé de las Casas, and twentieth-century Chicana writer Gloria Anzaldúa. Las Casas has long been considered a literary precursor to nineteenth- and twentieth-century Mexican American literature, as well as Latinx literature more broadly. Gloria Anzaldúa remains one of the most celebrated and influential late twentieth-century Chicana writers. More specifically, this analysis urges a reconsideration of las Casas’s founding influence, foregrounding his almost lifelong support for the enslavement of African people, as it also explores contemporary vestiges of the anti-Blackness strategically at the center of las Casas’s defense of Indigenous people of the Americas.