This chapter examines Chile’s transition to democracy, emphasizing the persistence and evolution of the 1980 Constitution’s political and economic framework. Rather than dismantling the neoliberal model inherited from the Pinochet regime, successive Concertación governments—led by Patricio Aylwin, Eduardo Frei Ruiz-Tagle, Ricardo Lagos, and Michelle Bachelet—consolidated and expanded it. The chapter highlights their shared achievements: Aylwin prioritized political stability and human rights; Frei Ruiz-Tagle oversaw economic growth and regional leadership; Lagos enacted constitutional reforms and modernization measures; and Bachelet emphasized social inclusivity. This period fostered political stability, poverty reduction, and international economic integration, affirming the system’s short-term success. However, by the late 2000s, structural limitations and internal political fractures within the coalition signaled growing fatigue. Critiques from the left and rising public frustration laid the groundwork for questioning the 1980 Constitution’s legitimacy. The victory of Sebastián Piñera and the conservative Alianza coalition in the 2009/2010 presidential election prompted traditional social democratic parties to shift leftward in an attempt to address emerging societal demands and reclaim power. This period ultimately set the stage for deeper political discontent in the following decade.