Incarcerated populations across the world have been found to be consistently and significantly more vulnerable to problem gambling than general populations in the same countries. In an effort to gain a more specific understanding of this vulnerability the present study applied latent class analysis and criminal career theory to gambling data collected from a sample of English and Scottish, male and female prisoners (N=1057). The analysis found six clusters measured by responses to the Problem Gambling Severity Index (PGSI), primarily distinguished by loss chasing behaviour. Longitudinal offending data drawn from the Police National Computer database found four criminal career types, distinguished by frequency and persistence over time. A significant association was found between higher level loss chasing and high rate offending in criminal careers. High rate offenders whose offending peaked in their mid 20’s were 5.3 times more likely to be higher level loss chasers and high rate chronic persistent offenders 3.7 times more likely than other criminal career types. Theories that link gambling, offending and impulse control are discussed and targeted interventions are proposed.