Using data collected at the Central Mississippi Correctional Facility, this research aimed to examine factors that affect the likelihood of re-offending by testing two models: a specific deterrence model and a proposed comparable capital model. Specifically, this research aimed to examine how economic, cultural, and social capital in the community, as well as in prison, affect self-reported likelihood of re-offending upon release, and to examine if these indicators are better suited for explaining offending as compared to those included in a deterrence model. By examining these effects, it was discovered that traditional deterrence and capital indicators alone do not provide a sufficient explanation of likelihood of re-offending. The proposed Capital and Punishment Model of Re-offending may provide a better way of conceptualizing offenders’ likelihood of re-offending upon release because it considers the effects of community and prison capital, while paying special attention to the effects of prior punishment.