The proposed study focuses on the investigation of the role of evaluation approaches in the governance of urban-regeneration operations with particular reference to the Multicriteria Analysis methods (Figueira et al. in Multiple criteria decision analysis: state of the art surveys. Springer, New York, 2005). There is, in fact, a strong need to take into account the various aspects involved in regeneration processes and programs, in order to contrast social decline, increase the inhabitants’ quality of life, enhance the cultural resources, valorize buildings and public spaces, protect the environmental system, stimulate economic development and so on. In particular, this paper considers the case of Cittavecchia, the historic centre of Trieste, where new investments are required due to several past recovery plans that left various problems unsolved, causing identity and trust issues. This study shares the framework with a wider research project where three regeneration scenarios for Cittavecchia have been evaluated and compared through a multicriteria approach (Crescenzo and De Matteis in Ri-centro: valutazione di scenari di riqualificazione urbana per il centro storico di Trieste attraverso l’Analisi Multicriteri. MS thesis, Politecnico di Torino, 2016) based on the Multi-Attribute Value Theory (MAVT) (Keeney and Raiffa in Decisions with multiple objectives: preferences and values trade-offs. Wiley, New York, 1976). MAVT enables the evaluation of the proposed alternatives and the identification of a successful network of planning and design strategies, thanks to its flexible framework that better simplifies, structures and sorts the existing fragmentation. MAVT is useful to support complex development processes because it considers multiple points of view, from the local communities’ needs, to governance and political ones. In particular, this paper is focused on the examination of the influence of socio-political aspects on decision-making processes, illustrating the calculation of the Coalition Index: an indicator that has been developed through the application of the NAIADE technique (Munda in Eur J Oper Res 158:662–677, 2004). This index makes it possible to consider the various actors’ opinions and to investigate the strength of the coalitions among the stakeholders involved in the transformation. Furthermore this method enables, with the contribution of local experts, the identification of the influence of stakeholders on the performance of the results and on the overall procedure, aiding decision makers to properly evaluate consequences and priorities, thus enhancing the transparency of the whole procedure. This study is a starting point for the evaluation of complex urban regeneration processes thanks to the ability of the proposed method to influence governance and urban planning procedures and even to adapt its framework to changes of conditions, objectives, criteria and needs.