The chapter presents the experiences of Argentina and Brazil and examines the conditions that have led to power two figures that can be thought of as tricksters – Mauricio Macri and Jair Messias Bolsonaro, respectively. We briefly contextualize some of the processes that took place in Latin America, particularly in Argentina and Brazil, presenting these two leaders that emerged in each of the countries. We describe their appearance on the public scene, their mode of operation and how they articulate and release, in very different ways, a trickster logic in national political life. Finally, we discuss the possibility and analytical utility of considering the figure of the trickster as a ‘collective personality’ – an entity formed by the leader and his political advisers or alter egos – to think leadership in contemporary democracies. In this sense, we seek to highlight aspects of the Argentinean and Brazilian experiences that, seen in light of the analytical references that guide this book, broaden the understanding of what is happening in each country. At the same time, we hope to contribute to sharpen the theoretical tools mobilized, such as ‘crisis’, ‘liminality’, ‘transition’, ‘schismogenesis’ and ‘trickster’.