In this study, we contribute to the emerging scholarship at the intersection of crime and health by estimating the effect of serious offending on offenders’ health. By building on sociological stress research, we identify and adjust for the key life course processes that may intervene on the pathway from offending to health using a rich set of measures available in the panel data from the National Longitudinal Study of Adolescent to Adult Health. Because offending and health share many causes and consequences, a critical challenge is accounting for confounding and mediation that unfold over time. We adjust for these time-varying processes by estimating repeated measures marginal structural models with inverse probability of treatment weights. The results show that offending over the life course is adversely linked to health but not uniformly across race and gender.