Popular in the field of developmental psychopathology, multifinality means that an initial condition or status can manifest in diverse outcomes across life. Using a near population of federal correctional clients selected from the Midwestern United States, the current study examined the association of chronic delinquent offender status on assorted life outcomes at midlife (average age of offenders was nearly 44 years). Although just 16% of the current offenders were formerly chronic delinquents, they accounted for 13.9% of current employment, 54.6% of antisocial personality disorder (ASPD) cases, 54% of those at the 90th percentile for arrest charges, 45.8% of those at the 90th percentile for assaultive arrest charges, 53% of gang activity, 43.8% of lifetime traumatic brain injury, and 22.9% of lifetime mental illness. Logistic regression models indicated that former chronic delinquency was associated with 41% reduced odds of employment, 897% increased odds of ASPD, 81% increased odds of 90th percentile offending, 82% increased odds of 90th percentile assaultive offending, 144% increased odds of gang activity, 115% increased odds of traumatic brain injury, and 141% increased odds of lifetime mental illness. Former chronic delinquency has more consistent predictive validity among males than females and among Whites than African Americans. Multifinality is a useful concept to understand the developmental course of chronic delinquency and assess noncriminal yet nevertheless socially and societally burdensome outcomes.