This chapter investigates the São Paulo Metropolitan Region and its governance challenges. The chapter describes the strategic interactions between different levels of government (federal, state, and municipal) as they attempt to create and implement metropolitan governance mechanisms. It also examines the impacts of political fragmentation and the vast inequalities that exist among the region’s 39 municipalities. The chapter explores how, despite the autonomy granted to states and municipalities by Brazil’s federalist system, there is a lack of an effective metropolitan governance and regulation of urban affairs involving all levels of government. The analysis also investigates critical public issues such as mobility and transportation, access to drinking water, housing, and crime to illustrate the consequences of administrative fragmentation on public policy implementation. The study underscores a “metropolitan paradox” where the formal existence of a metropolitan region doesn’t necessarily translate into effective, coordinated governance. This case study also discusses how Brazil’s national political and legal context, particularly its federalist structure, influences the development of interjurisdictional collaboration and limits the effectiveness of policies aimed at addressing urban issues.