This chapter examines the development of the Metropolitan Region of Santiago, focusing on the evolution of its governance from a military dictatorship to its current democratic framework. Santiago has progressed toward metropolitan governance despite a failed constitutional reform in 2022 that aimed to transform the country into a regional state. The chapter suggests that the Santiago metropolitan region, which was initially established for centralized planning, has been unable to effectively address regional issues despite attempts at decentralization during the democratic period. The chapter also highlights significant progress in establishing a metropolitan governance framework, including the approval of laws that enable citizens to elect regional governors for the first time, marking a major political and administrative milestone. The Chilean case exemplifies how a long-planned decentralization process, including legal, political, and constitutional reforms, facilitates a transition toward more effective urban governance.