This contribution presents the results of the research group’s activities carried out within the PRIN 2022 project “Confiscated Asset in Transition: from the Anti-city to the Third Heritage”, as part of a research agreement with the Municipality of Naples and the Agency for Confiscated Assets. The research activity involved students from the Department of Architecture of Naples and several local stakeholders, and it entailed the development of a transdisciplinary and multi-actor decision-making process. This process hybridised different methodologies such as multi-criteria and multi-group evaluations, economic assessments, and urban and architectural design. The methodological approach was implemented starting from the selection of assets confiscated from organised crime within the municipality of Naples. In line with the need to “return these assets to the community”, as prescribed by Italian legislation on this topic, the aim was to define time-based strategies for incremental reactivation and adaptive reuse, with particular attention to the direct and indirect benefits generated in the local context. Through the identification of different phases of evaluation and design, several future scenarios were developed to ensure multidimensional impacts, economic, environmental, social, and cultural. The paper explores the potential of a multidisciplinary approach to decision-making in defining scenarios for the regeneration of disused urban assets, highlighting the tools adopted throughout the research and educational process.