Focusing on Villa Alta, Oaxaca, a rugged, mountainous, and remote region of New Spain, this rich social and cultural history tells the story of the dynamic period prior to and after the Cajonos Rebellion of 1700 through the eyes of native intermediary figures: indigenous elites conversant in Spanish language and legal rhetoric. Early in their rule, Spanish officials had identified the native nobility as a caste of intermediaries who could help administer colonial society. Due to a lack of Spanish residents and personnel in the remote region of Villa Alta, bicultural native leaders participated more actively in the making of colonialism there than did indigenous people in colonial centres where many more Spaniards lived.From 1660 until Mexican independence in 1810, native leaders in the district of Villa Alta redefined native political leadership and helped to construct the symbolic order that allowed Spanish colonialism to endure despite the absence of a standing army. Yet, the native nobles who learned to speak and write in Latin and Spanish and successfully petitioned the Crown to wear Spanish silks, carry swords, and ride horses had to answer not only to their Spanish overlords but also to the indigenous populace. Through their roles in village government, the Catholic Church, the legal system, and the Spanish system of forced labour and production, native brokers mediated between the competing demands of Spaniards and indigenous people, holding the colonial order in balance. Most often, they defused tensions within colonial society, but on occasion, as during the Cajonos Rebellion, the pressures were such that they abandoned the middle ground.