The waterfront regeneration of Valparaiso in Chile has been the expression of significant institutional efforts aimed at reaching the so-called urban renaissance of the port-city, seeking to overcome the sustained symptoms of urban decay and economic underperformance. Over the years, a locally born idea became a controversial proposal led by the central government: A privately developed commercial project, named Puerto Baron (Baron Port). This article explores spatialized political struggles both underpinning and undermining this project, from institutional and elite interests pushing its realization to social actions triggering its end. In Valparaiso political and economic forces coalesced across different scales in their attempt to materialize a project that transfers globalized spatial imaginaries with tangled territorialized politics that exceed the limits of the city. Although state-led entrepreneurialism sets the waterfront regeneration agenda, interdependencies with networks of elites and local government were key to sustaining the project. In opposition, social movement strategies of scale jumping help to contest and influence the project’s delay. The case highlights the fragile nature of governing coalitions in Valparaiso as a shift in municipal power, which brought an alignment towards grassroots actors, ended the rather flawed regeneration project of Baron Port. The paper shows how unbounded spatial politics become highly permeated by interests at different scales, though still dependent on national centralized actions and definitions.