Don Bartolomé Tupa Hallicalla (1603-1684), ‘cacique’ of Asillo in Azángaro province (North of Lake Titicaca), was for three decades, between 1645 and 1675, a successful ‘colonial entrepreneur’ in the Southern Andes. He offered support to local Spanish authorities against a mestizo uprising in 1661, was appointed Indian infantry captain by the viceroy in 1663, obtained special legal immunity from the Audiencia of Charcas in 1664, married into the Inca nobility of Cuzco, and received a viceregal appointment as ‘Camp Master’ of the Indians of the city of Cuzco in 1671. As reward for this decade of loyal support, in 1673 he even requested the Crown for an ‘encomienda’ (a rent from Indian tribute). But in the next few years, due to a conflict with the religious authorities of Cuzco, he lost his post as ‘cacique’ and spent his last years almost in poverty. During this conflict, he was accused of participating in an anti-colonial conspiracy discovered in Lima in 1666. Was don Bartolomé a ‘colonial broker’ or an ‘Indian rebel’? What this case tells us about mid-colonial indigenous communities, their ethnic leaders, and the different economic and politic networks they were part of in the Southern Andes?