When Lisbon inaugurated Expo 98 in the Oriente district, converting a degraded industrial area into a leisure area attached to an intermodal hub, it seemed to be understood that the Portuguese-speaking capital was entering the competitive space of metropolises subject to international evaluation standards. Accompanying a gesture of exaltation resulting from the April ‘74 Movement, successive governments promised to turn Portugal towards the European Community, with a view to a resolutely progressive future. Lisbon became a beacon for national policy, and the modernisation fronts that were established then were reified as indicators of quality of life likely to generate international attractiveness. This was without taking into account the twists and turns of destiny that, between the financial crisis, the return of austerity, speculative pressure, post-colonial contestation and over-tourism, would somewhat tarnish the initial beautiful projects. Based on extracts from a field notebook that has been filled in over the last twenty years, this paper will trace the thread of an urbanistic epic with bitter and melancholic contours.