One of 52 theoretical papers on school crime and its relation to poverty, this chapter describes the Childcare Apprenticeship Program at a special day school for 50 adolescents operating under the auspices of the Harvard Graduate School of Education. The program is a three-year, cross-age experiment that paired troubled adolescents and children from deprived neighborhoods. The theoretical focus of the program was empathy--the encouraging of empathic responding between adolescent and child as a "double-benefit" experience for both. The program has established the preventative value of cross-age childcare as a means of increasing self-esteem, feelings of competence, and empathy for others in formerly delinquent or disturbed youth. (Author/MLF)