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Criminological and sociological research has extensively examined important relationships between crime, work, and educational outcomes, such as school enrollment and dropout. This line of research shows that delinquency and intensive work (i.e., greater than 20 hours per week) are associated with an increased risk of high school dropout. However, the focus on minor delinquency, criminal justice contact, and work intensity in prior research might obfuscate the importance of other dimensions. It is plausible that youth more active in crime and/or work earn more money than youth who are less active. Earnings, no matter the source, may provide an incentive to disengage from school above and beyond the time these activities take away from school related activities. I consider this possibility by utilizing data from the Pathways to Desistance study, which contains a sample of serious adolescent offenders, to examine how 1) monetary returns to crime and 2) monetary returns to work map onto patterns of school enrollment and high school dropout. Consideration will be given to the types of crime, frequency of offending, and intensity of work. Results will be discussed in light of theoretical and policy implications.