In the period following “independence” of the former Spanish Empire in the Americas, many of the new nation-states struggled to establish peaceful regimes in the ensuing vacuum of power. What becomes clear is a linear conception of development (in the broad, historical sense) largely defined by Eurocentric (and therefore colonial) ideology. The binary between barbarism and civilization points to the two extremes of this imported historical-determinist trajectory. In turn, the ideal of civilization became dominated by the subsequent royalist-republican binary (along liberal-conservative lines). Through the analysis of the concept of caudillismo, however, many of the hypocrisies and paradoxes of this trajectory are exposed. Populist in their imperative of rallying armed support for their ‘movements,’ caudillos occupy a space between the opposite ends of these civilized-barbarous, and republican-monarchist binaries, often crushed by an eventual leaning to one side, letting down the rallied masses. The example of Urvina in Venezuela illustrates this trend (p 54). He won popular, largely indigenous support by attacking traditional (colonial) oppressors, namely the Catholic Church and large landholders, establishing an Indian Protectorate. However, as property rights being a central tenant of liberalism (at the time), the “parcelization of indigenous land” which effectively expropriated many local populations, led to Urvina’s eventual dearth of support. Urvina, like many of his caudillo contemporaries, failed to transcend the binarized logic of his persistently colonial paradigm. Is there importance to the (relative) prosperity of indigenous and lower class folks in the period of post-independence (relative) anarchy? Is there political ideology common to Latin America’s various caudillos? In light of this, how is caudillismo similar to the rise in non- or post-partisan populism in the 21st century? If there exists a parallel, what is the false-choice we are contemporarily blinded by, or unable to transcend?