The replacement of an entire symbolic order by another, the creation of images and representations – bringing new ideas – of revolutionary leaders and still unstable nations are issues that have not yet been considered by the historians of the American Independence Wars. The portraits of heroes have traditionally been studied in the narrow context of the borders drawn much later, looking for a ‘truth’ in the traits of these characters that the construction of historical narratives has identified as the founding fathers of nations. The celebration of the bicentenary of American emancipation processes was an opportunity for comparative studies of this construction, as the tensions and critical wealth of these images are still seen as the visible face of patriotic ideas, especially in school education (see the international research project: ‘José Gil de Castro. Visual culture and representation, of the Former Regime to the Republics of South America’). In this article, I propose an analysis of a few portraits of Libertadores, among those who have had the most ‘success’ over time. On the one hand, how do traditions, namely colonial art, French neo-classicism and Napoleonic iconography, inter alia, influence these portraits and, on the other hand, what innovations – introduced by these portraits – alter these traditions? As regards the reception of these images, from a comparative perspective, I will pay particular attention to the interactions between the style, aesthetic value and historical veracity attributed to these works, in order to assess the scope of these portraits as iconographic documents and for the artistic history of American nations. How did images, and in particular portraits, play in the history of political conflicts?