The paper examines the antecedents of criminal behavior through the process of retrospective family and life course histories in which incarcerated male inmates and male university students are compared. The main focus is on early childhood experiences and parental behaviors. The study data derive from intensive, face-to-face interviews with 38 men incarcerated for violent offences and a matched group of 66 men attending university at the same time. The interviews focus on the relative importance of adverse childhood experiences and linkages with adolescence. The interviews demonstrated that nearly four-fifths of the inmates experienced toxic family environments by the time they reached adolescence, as compared with only two of the university students. Qualitative analyses flesh out the major themes, experiences, and "risk factors" that helped shape the trajectories of both groups of men. The socially toxic family environments and sub-optimal parenting practices that most inmates endured produced long-term, adverse effects in reducing their capacities for resilience, forging healthy relationships with their peers, and remaining in school.