This paper presents insights from qualitative research into organised crime (OC) in Glasgow, Scotland. Interviews were conducted with a sample of 42 current and former offenders with a history of group offending in an attempt to understand variation in the onset, maintenance, and cessation of OC careers. Offending narratives revealed different OC trajectories. Drug dealing was the primary modus operandi of OC groups, but some offenders exhibited versatility and progression to wider criminal activity or a mix of illegitimate activity and legitimate business. Implications for future policing strategies and suggested additional research are outlined in response to these findings.