Researchers have hypothesized that over the life course, criminal offending varies with problems in other domains, including life failure and physical and mental health.To examine this issue, the authors use data from the Cambridge Study in Delinquent Development, a prospective longitudinal survey of 411 South London males first studied at age 8 in 1961. Developmental trajectories of criminal activity were defined on the basis of conviction records through age 40, and these were used to predict self-report measures of life failure at age 48 obtained during personal interviews. Results indicate that offending in the first 40 years of life relates to life failure, that childhood risk factors are also implicated in adult life outcomes, and that differences emerge in how offender trajectories predict life failure after controlling for individual and environmental risk factors. This is the first longitudinal investigation to show that chronic offending is associated with life failure into the late 40s, an age period not previously reported, and it also shows that different offending trajectories have different outcomes in late middle age.