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The life course perspective emphasizes “turning points” or events and transitions in the lives of individuals that substantially alter life trajectories. Much research exists to support the assertions that formerly incarcerated offenders are blocked from success in legal markets, which suggests that incarceration may serve as a turning point. However, despite the large body of research examining the effect of incarceration on legal earnings and a growing consensus that incarceration has either null or criminogenic effects at the individual level, there are relatively few studies that have examined the potential impact of incarceration on illegal earnings. Using the first 7 waves of data from the National Longitudinal Survey of Youth 1997, we examine both binary and continuous measures of illegal earnings utilizing a within-person analysis of boys who reported delinquent behavior in adolescence to examine whether a change in incarceration status leads to a negative, null, or positive change in illegal earnings. Preliminary results suggest that the effect of incarceration on illegal earnings may be small and positive, or that the effect may be due to selection. Implications of the findings will be discussed.