This thesis aims to contextualize and understand the current mobilizations in Chile. The research is along four major theoretical axes— first, democracy and transitions from authoritarianism; second, neoliberalism and commodification; third, inequality; and fourth, cycles of mobilization. In Chile, the puzzle of mobilization has a number of contributing factors that are explored throughout this thesis, including an in depth look at specific social, education, and pension policy. My research concludes that the current mobilizations can be attributed to the complex and intertwining fields of structural legacies from the dictatorship, incomplete transition to democracy, inequality, persistent and rampant commodification and neoliberal policy, and cycles of mobilization. All of these factors have influenced one another and worked to create conditions of a crisis in representation and extreme popular discontent that exploded in October, 2019.