During the 1990s, Paleoconservatives and radical libertarians joined forces to form a fleeting alliance: the Paleolibertarian coalition. This study’s distinctive contribution is that it examines the Paleolibertarian collaboration as a failed attempt at coalition building and draws out broader implications for understanding the radical right. The Paleolibertarian coalition brought together competing agendas, and the coalition included critics of capitalism (the Paleoconservatives) and proponents of unleashing the market (the radical libertarians). What united Paleoconservatives and radical libertarians in the first place, and what broader lessons can be drawn from the coalition’s failure? As I claim, the Paleoconservatives and radical libertarians endorsed parallel views – they yearned for an organic order and local control – but for distinct reasons. Ultimately, the two factions disagreed on the preconditions for social order, particularly about the necessity of state intervention. Examining the coalition’s contradictions promotes our understanding of the doctrine’s peculiar sociology and also how Paleolibertarianism shaped successor ideologies on the radical right. I discuss how the Alt-Right intellectual Richard Spencer absorbed Paleolibertarianism’s lessons. This paper lays the groundwork for further research into the Alt-Right, and how the Paleolibertarian coalition formed the precedent for an ideology embracing an ethno-state.