Researchers have called for greater attention to be paid to the variables linking unemployment to crime. In particular it has been suggested that people’s interpretation of their labor market situation plays a large role in shaping their response to it. This research examines the role that unemployment plays in the criminal behavior of 400 homeless street youth. Of particular interest is the way that these youths interpret their labour market experiences and how together these interpretations and experiences influence their criminal behavior. Beyond the length of unemployment issues to be explored in the paper include a number of different causal attributions for unemployment, a variety of emotional reactions to unemployment, as well as issues surrounding work ethic and employment commitment. Further these youths’ subjective interpretations of their financial situations, perceptions of relative deprivation, and acceptance of inequality will also be explored.