As Italy’s main financial hub and a global capital for fashion and design, Milan has, in recent years, undergone notable transformations in its cultural and artistic landscape. This evolution, shaped by the creation of new institutions and the redefinition of entire districts, reflects a broader dynamic of internalizationation and urban renewal. The 2015 Milan Expo was a critical catalyst in this process, exemplified by the Porta Romana district’s transformation following the opening of Fondazione Prada. Although the changes unfolded in a more gradual and stratified manner than in other European metropolises, such as Berlin, where the urban structure and ecosystem for art and culture developed in tandem, undergoing abrupt changes in a short period, it nonetheless introduced new frameworks for the production and circulation of contemporary art.