Nearly half a century ago, a star-crossed adolescent found himself at an important crossroads. Just five months shy of his eighteenth birthday and newly released from an 18-month court commitment to the Pennsylvania George Junior Republic School for Boys (Brown, 1983), a congregate facility for court-adjudicated delinquents and foster youth, he was a prime candidate for the adult correctional system. It was a fate for which he seemed destined based upon his many family and school failings and his history of emotional and behavioral problems. In this article, the author chronicles the life span development of this youth who experienced extreme conflict in family, school and community--and the forces that led to healing and resilience.