This paper offers an interpretative reading of Enzo Catarsi’s pedagogical thought by proposing a specific focus on the ethical and aesthetic dimensions of human relations in places of education. Through a number of “excerpts” taken from Enzo Catarsi’s extensive scholarly production, several recurring themes are presented that accompanied his teachings and that represent, today, a cultural heritage of great educational depth for its current and future-oriented characters. The secrets of Enzo Catarsi’s legacy are found in democratic commitment and the courage of utopia. These professional behaviors represent the founding foundations of a broader a pedagogical horizon consisting of specific educational actions to be supported and implemented: teaching as encouragement, the role of affects, emotions and empathy, art and passion, the importance of recognition through an authentic gaze and the engagement to supporting processes of transformation, evolution and growth.