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What are the causes of the piracy that harried Colonial Latin America? Epic poems of the sixteenth and seventeenth centuries account for the multiple economic, political and legal factors that contributed to the phenomenon, but they rather surprising also provide a consistent psychological explanation. According the epics such as Elegías de varones ilustres de Indias, La Dragontea and Armas antárticas, all the robbery, raiding and terrorizing of pirates can be traced back to a single pensamiento. In these poems, mariners such as Francis Drake and Thomas Cavendish are not born pirates, but rather they become pirates. They contemplate their objectives of social and economic advancement and hit upon a course of action that capitalizes on their navigational skills and experience. It happens, however, that the portrayal of pirates’ thinking resembles the functioning of a defective imagination as described in such texts as Pico della Mirandola’s On imagination. In this treatise, as in others like it, an unhealthy imagination is susceptible to evil influences and leads to perceptions that ultimately have destructive effects. This paper explores the portrayal of the pirates’ pensamiento in the poems above as well as in precursor epics such as Carlo famoso and Os Lusíadas. In addition to examining the relation of pensamiento to imaginación, this paper also analyzes related concepts such as invención and ingenio. Accounting for piratical psychology allows the poems to attribute immoral and unethical motives to maritime enterprises that threaten Spanish authority over overseas territories at the moment of their conception.