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The association between income and offending is well-studied. Less well-studied is whether that association varies by income source. This project examines whether the proportions of income that are derived from legal earnings, unearned income, illegal earnings, parental transfers, and other sources are differentially associated with arrest, self-report offending, and substance use. Using data from the National Longitudinal Survey of Youth—1997 Cohort, we first describe the income “portfolios” of individuals—that is, the allocation of their total income across sources—and whether those portfolios vary by previous involvement in crime and deviance. We then use fixed effects models to examine whether income portfolios predict future crime and deviance above and beyond the impact of the total amount of income received. Implications of the findings for work on stratification and crime are discussed.