To investigate changes in characteristics of delinquents over time, randomly selected contemporary delinquents (Zagar, et al., 1980–1988; n = 2,031) were compared with 3 historical Chicago and Boston samples (Healy & Bonner, 1909–1915, n = 2,000; Healy & Bonner, 1917–1923, n = 2,000; Glueck & Glueck, 1917–1922, n = 1,000). All underwent physical, psychiatric, psychological, school, and social examinations. Contemporary delinquents had more assault, burglary, homicide, alcohol and substance abuse, gang membership, head injury, overdose, and single parents. Historical delinquent samples had more thieves and families with both biological parents. Historical delinquent mean IQ was 5 points below standardization average; modern delinquents were 22 points lower. Contemporary offenders were a greater portion of the county public school-aged population. Current more sensitive and specific examinations account for increases in observed overdoses and head injuries in the 1980s sample. Other demographic differences between contemporary and 3 historical delinquent samples were robust. Findings are discussed with respect to a need for early actuarial assessment and empirical treatment of the costliest delinquents: the dropouts, alcoholics, addicts, career delinquents-criminals, and homicide-prone youth.