In my dissertation I study the ways in which the literary figures of free males on horseback, the Cossacks and the gauchos, were endowed with political meanings in the River Plate and Ukraine of the 1830s and 1840s. My study is located within the field of history of political culture with special attention paid to ideology, its symbolical representations and the ways in which they formed part of broader mythologies. The two cases are not studied for their own sake, but as examples of complex ideological tensions caused by the expansion of state and the transformation of bourgeois society. What brings their stories together is their having a common point of reference in the late Enlightenment/Romantic fantasy of ‘nonmodernity’ of which the anarchic frontier horseman is just one symbol. The overarching question that I address is how several different actors in their contingent environments employed these symbols to construct the male subject of modern politics (modernity being understood here as a disciplinary myth and a claim-making concept, rather than a tangible historical condition). I offer contextualized interpretations of several texts: verse journals directed at uneducated subalterns of Buenos Aires at the beginning of 1830s; a historical novel by Nikolai Gogol; a celebrated biographical essay by Domingo F. Sarmiento; pulp novels, secret reports, memoirs and propaganda dossiers of Michał Czajkowski, a Polish-Lithuanian politician and military commander based in Istanbul; Polishand Ukrainian-language writings of several minor authors from Austrian Galicia. I show that the Cossack/gaucho myths are just two examples of dream about the free life beyond the limitations imposed by the state and society. In fact, that dream was present in many other environments and took many different guises, US cowboys being just one obvious, though chronologically later, example. Such longings were inextricably linked to the global ‘structured transformations’ interpreted by the historical actors as the rise of ‘modernity,’ though clearly the figure of anarchic frontier horseman was not the only conceptual tool used to cope with them. What made the Cossack/gaucho myths so successful was that they were a very specific antithesis of ‘modernity,’ one that combined 1) the rejection of state and family; 2) the claim to be truly native; 3) and the promise of liberating the repressed masculine instincts.