The education field favors innovations, but innovative schools tend to fade after an initial 'golden age.' According to the new institutional theory, this happens due to the innovative school's need to achieve institutional legitimacy, which encounters several difficulties. This study aims to explore the journey to attaining legitimacy in one entrepreneurial school that gained legitimacy from some actors, but not from other relevant ones, and did not survive. Using a case study method, 30 interviews were conducted, and over 200 documents, including media articles, school protocols, and court protocols, were analyzed. The findings reveal that the concept of legitimacy is not dichotomous, but a continuum ranging from legitimacy to neutral and de-legitimacy, and stakeholders differ in their positions, resources, and type of legitimacy. Additional theoretical and practical implications are presented in the discussion.