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This paper suggests that the prototype leader of Latin America is a caudillo, a strongman leader. The author substantiates the suggestion that “caudillismo” is one of the predominant prototypes of leadership in Latin America from various historical and cultural perspectives, intermingled with examples from her own experiences. Prototypicality (categorization theory) is explained and diagrammed together with its implications for leadership. A working definition for leadership in a collectivistic society is provided together with the etymology of caudillismo. The author proposes that caudillismo (the practice of strongman leadership) springs from the ethos of Latin America’s monolithic Catholicism. This ethos or cultural conditioning of Latin America is embodied by five overarching values (generosity, dignity, leisure, grandeur, and manliness). These values give fertile ground to caudillismo as a prototype or culturally endorsed implicit leadership theory. These cultural values are explained and both the virtuous and shadow sides of caudillismo are described. The paper offers some reflection questions and practical implications for expatriates like understanding one’s own leadership prototypes, learning to name the tension one experiences with the differences in leadership expectations, needing to broaden one’s categories of right and wrong, recognizing one’s limitations, receiving the gift of contact with another culture, discerning judiciously and respecting the caudillo.