This study draws on theories of stigma, social and human capital, and opportunity structure to assess the role of prior incarceration on illegal earnings. Tobit regression models are estimated for young adult ex-offenders and nonoffenders using the National Longitudinal Survey of Youth for 1997 to 2005. The findings reveal that individuals with an incarceration history earn significantly higher annual illegal earnings than those who do not have such a history. This is true net a variety of predictors of illegal income, including race and ethnicity. The current research indicates that spending significant time in jail or prison may force the ex-incarcerated into illegal opportunity structures to obtain income.