This chapter explores the technopolitical dynamics underpinning the monopolistic rise of data-opolies—dominant tech corporations such as GAFAM—and their implications for democracy in the age of AI. Drawing on Calzada’s conceptual framework and action research, it investigates how algorithmic governance in smart cities displaces democratic deliberation, eroding civic trust and transparency. The chapter critically engages with Web3 technologies—blockchain, DAOs, and data cooperatives—as possible countermeasures to platform capitalism, while remaining attentive to their ideological tensions, especially the crypto-libertarian vision of “Network States” à la Srinivasan. By linking the governance of AI systems with Richard R. Nelson’s “Moon and Ghetto” metaphor, the chapter underscores a key paradox: technological innovation soars, yet foundational democratic deficits remain unresolved. Through a multidisciplinary lens, it interrogates how decentralized infrastructures might reclaim digital sovereignty and foster more equitable innovation systems. The chapter concludes by proposing a pluralistic governance model rooted in algorithmic transparency, data ethics by design, and multistakeholder engagement—critical steps toward re-democratizing the datafied city.