It is well known that there is no clear consensus with respect to the relationship between unemployment and crime. As well, there is very little aggregate-level research on the linkages between crime and the educational experiences of young people. In this paper we argue that a better way of thinking about the property crime - unemployment nexus involves modeling the role of unemployment duration, and we show a very strong positive relationship between criminal activity and the extent of youth male long-term unemployment. We also produce evidence of a negative association between criminal activity and high school completions, and positive associations between criminal activity and unsuccessful senior high school participation. The analysis suggests that labour market and education policies have the potential to significantly reduce property crime. However, increased high school participation of the long-term unemployed only seems to decrease crime if it results in graduation. This suggests that the effectiveness of education policy is a significant influence on property crime activity, a unique finding.