My presentation will explore how Toledo’s case against the Chiriguanaes reflects the larger context of establishing the legitimacy of Spanish rule in the Americas and particularly the compromise position expressed by the influential Dominican philosopher Francisco de Vitoria and his followers. I will show that the questions and testimony that make up Toledo’s investigation explicitly aim to characterize the Chiriguanaes as subject to conquest under Vitoria’s títulos legítimos (just titles) for imperial rule. This effort reflects a simultaneous effort by Toledo to justify Spanish rule throughout the former Inca realms by commissioning a history by Pedro Sarmiento de Gamboa that characterized Inca rule as illegitimate. I also argue that Toledo and Vitoria shared a sense of practicality that influenced their juridical reasoning—one that led Vitoria to see the Spanish Indies as a fait accompli and Toledo to take the fairly extreme step of authorizing not only the violent conquest of the Chiriguanaes but also the enslavement of captives taken during the war.