This longitudinal study extended previous work of Wiesner and Capaldi (2003) by examining the validity of differing offending pathways and the prediction from the pathways to substance use and depressive symptoms for 204 young men. Findings from this study indicated good external validity of the offending trajectories. Further, substance use and depressive symptoms in young adulthood (i.e., ages 23-24 through 25-26 years) varied depending on different trajectories of offending from early adolescence to young adulthood (i.e., ages 12-13 through 23-24 years), even after controlling for antisocial propensity, parental criminality, demographic factors, and prior levels of each outcome. Specifically, chronic high-level offenders had higher levels of depressive symptoms and engaged more often in drug use compared with very rare, decreasing low-level, and decreasing high-level offenders. Chronic low-level offenders, in contrast, displayed fewer systematic differences compared with the two decreasing offender groups and the chronic high-level offenders. The findings supported the contention that varying courses of offending may have plausible causal effects on young adult outcomes beyond the effects of an underlying propensity for crime.