To elaborate past research, this study examines the course of specialization and versatility with maturation and contends that specialization develops in a nonrandom manner, as suggested by the orthogenic principle of human development. To examine the development of specialization and versatility, forward specialization coefficients were disaggregated for three age cohorts over a 20-year follow-up period in a sample of high-risk youth (n = 3,652) with 54,175 arrests. Results show that forward specialization coefficients were generally of moderate magnitude and, across age cohorts, developed modestly in an age-graded manner for the youngest cohort. In conclusion, the results provide preliminary support for the orthogenic theory among early first-admission youth.