Javier Milei’s rise baffled many analysts across the world. An especially difficult part of the phenomenon of the newly elected Argentinian president is his political thought. This paper seeks to explain the sources of his anarcho-capitalism and also considers the extent to which a radical leader can adopt a politically pragmatic approach. The analysis also attempts to explain the connection between libertarianism and conservatism in Milei’s thought. The main sources considered are the writings and public speeches of Javier Milei, alongside the extant literature and the referenced ideological sources of the president.