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We specify an individual-level model linking crime desistance to estimates of legal risk, differential expectations, degree of past success at legitimate and criminal pursuits, and age. OLS and logistic regression procedures are used to estimate the model using longitudinal data on serious, previously imprisoned offenders. As predicted, age decreases estimates of the likely payoffs from crime and legitimate employment. Contrary to predictions, age is unrelated to the perceived legal risk of renewed criminal participation. Age, past success at avoiding confinement, expectations of success from crime, and level of education are significant predictors of crime desistance. Neither the perceived legal risk of crime nor expectations of success through straight pursuits significantly predict desistance. We suggest an interpretation for these anomalous findings.