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). Theoretical links between gambling and crime were tested through three hypotheses: (1) that prisoners in the UK would have higher rates of problem gambling behaviour than the national population; (2) that if the link between gambling and crime is coincidental, gambling behaviour would be highly prevalent in an offending population, and (3) if connections between gambling behaviour and offending are co-symptomatic a mediating factor would show a strong association. The first of these was supported, the second was not supported and the third was partially supported. Latent class analysis found six gambling behaviour clusters measured by responses to the Problem Gambling Severity Index, 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 suggesting that impulse control may be a mediating factor for both gambling harm and criminal careers.