The work of Piero Bertolini crucially influenced the pedagogical study of juvenile delinquency in Italy. His theoretical contribution changed the dominant interpretative paradigm, which had previously been informed by a psychological/medical and corrective model. By redefining rehabilitation and introducing the key notion of “intentional consciousness” as a basis for helping subjects to take responsibility for their conduct, Bertolini prompted educators to adopt a new perspective and to reconsider their own stance within their educational work with teenage offenders. Although this novel educational focus demands a different emphasis on the young person’s subjectivity, it is not enough to reflect on the “subject”: the importance attributed by Bertolini to “education as a field of experience” means that, in engaging with his “tough kids”, we must also take due account of the “materiality” of education, while remaining within a phenomenological framework. This is one aspect of the contemporary relevance of “Per una pedagogia del ragazzo difficile” (Pedagogy for troublesome juvenile, 1965) for a book that speaks directly and meaningfully to the professional development of today’s new generations of education practitioners.