To evaluate the impact of a cultural initiative is a complex endeavour. We will analyse the topic on the example of European Capitals of Culture. Their coming into existence is highly entrenched with emotions, at the beginning often pushed by enthusiastic members of mostly small groups, overcoming the obstacles of a bidding-process, finally, in case of winning the title, trying not to become victims of success. There are moments of disenchantment when management and politics cause controversial decision-making. Also, it is often ambivalent what the legacy will be. In addition, there is evaluation: A distant, indicator-driven attempt to gain transparency of initial ambitions, what took place in the title-year and will probably remain after. Do these constructions of ambitions, ‘reality’ and its assessment go together? Where are the limits in representing what a European Capital of Culture means, and to whom? What are consequences on practical and theoretical level because of perceived differences between organizational life and its evaluation? We refer to these topics in our research on evaluation by taking an empirical view, presenting an in- depth case study of the European Capital of Culture Matera-Basilicata 2019 in diverse phases of its becoming. Each phase within the lifespan of this temporary organization is to characterize by specific merits and limitations of its evaluative activities. The rationale of evaluating European Capitals of Culture, deconstructed against the background of critical perspectives on evaluation research, supports a skeptical turn in evaluation research. We delineate a possible development of evaluation by referring to aesthetic perspectives in and on evaluating European Capitals of Culture. Hereby, we refer to artists in residence and city writers as role models and learning fields.