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In this life course history of a former gang leader and now highly reputed credible messenger we see how his transformational pathway problematizes pathological assumptions about gangs and their memberships. Based on multiple interviews over the course of a 5-year evaluation study this historical subject describes his time in prison as well as his post-imprisonment search for employment, efforts to rebuild his self-confidence, and assume a new identity in the burgeoning movement of ‘credible messengers’ and anti-violence interventions. The analysis of his conceptions, motives and actions of resistance and survival tells us much about the possible futures of gang members as transformative mentors. The presentation is divided into three thematic sections. The first considers the life of the subject as he adapts to prison life and develops important modes of survival that became important for his progress during his post-incarceration trajectory. The second explores his modes of integration post-incarceration and the impact of the constant gaze of the State. The third focuses on his ability to ‘get a break’ that creates the ‘second chance’ to remake himself as a credible messenger.