This chapter examines the emergence of a rupturist discourse in Chilean politics between 2010 and 2018 and traces its origins through three interconnected developments. First, the internal divide within the Concertación coalition—between autoflagelantes (advocates for radical reforms) and autocomplacientes (supporters of gradualism)—fractured the coalition’s coherence and introduced alternative ideas. Second, the rise of a younger generation of leaders, shaped by the student protests in 2006 and 2011, introduced bold demands and a grassroots challenge to the status quo. Third, the second presidency of Michelle Bachelet embraced structural reforms in taxation, education, and electoral systems, which demonstrated the feasibility of transformative change. These forces converged against the background of the erosion of voter–party linkages and party system fragmentation, producing a fertile environment for systemic critique and rupturist narratives. By 2018, changes were noted in the boundaries of Chile’s political possibilities, thus setting a higher bar for future reforms and laying the groundwork for the dramatic events of 2019. This chapter argues that the interplay among ambition, generational leadership, and institutional reform catalyzed a new era of politics in Chile that was defined by the pursuit of bold, systemic, and unapologetic change.