This case series describes one of the world’s most remarkable communities, which for the past twenty years has continuously achieved extraordinary results working with marginalized individuals. Case C plunges into organizational structure issues and the realities of change management at San Patrignano. It also poses the fundamental leadership issue of what leadership profile is right for a community of this kind, and to what extent such leaders can be attracted from the outside and/or groomed from within. This issue is fundamental for corporations that look at the key aspects of non-profit communities such as San Patrignano as potentially alternative organizational and operational models.