This article explores connections between social strain, constructions and practices of masculinity and the prevalence of violence among a white working-class male demographic. The study’s evidence-base is qualitative research conducted in Scotland. It utilized life history interviews with a clinically significant sample of 40 incarcerated young male offenders convicted of violent crimes. Family, school and peer group ‘pressures’ coloured these young men’s trajectories to persistent violent reoffending. Their language highlights attachment and betrayal issues. Masculinity associated with Scottish history is a resource within Scotland which may impact on contemporary practices of masculinity. The article’s dominant thesis is that the young men’s violence reflects immersion in traumatic life histories. The masculinized cultures they encounter are likely to produce violence and limit opportunities which could help ameliorate attachment trauma.