A twin crisis of democratic representation and socio-economic precarity created space for anti-system outsiders to emerge on the left flank of traditional party-systems in Bolivia and Venezuela, paving the way for a “post-neoliberal” democratization process. Over the course of the projects headed by Evo Morales in Bolivia and Hugo Chávez and his successor Nicolás Maduro in Venezuela, however, power struggles emerged between a recalcitrant elite, the left-led government, and organized popular sectors. These tensions shaped the pathways that processes followed, with simultaneous democratization and de-democratization occurring whereby a partial deepening and extending of democratic quality for popular sectors was accompanied by the bending of liberal norms. Comparing the varying balance and forms of power between competing actors, this book offers a novel and rich explanation of the partial and stuttering efforts to advance a post-neoliberal democracy in Bolivia and Venezuela.