The purposes of this study were to evaluate a pilot, dropout prevention program designed to provide academic tutoring and supplemental enrichment to 9th graders and to examine additional data on adolescents' motivators and role models related to high school dropout and completion. The program targeted 9th graders because many adolescents decide to drop out of high school at age 16, which occurs for most in the 10th grade. Students were from a major city in the midwest, and were 99% African American and of lower socioeconomic levels. The findings indicated that students appeared to benefit from the opportunity to develop close relations with adult tutors who cared about their success. The dropout rate for students in this program was much lower than that of 9th graders in that high school who were not in the program, as well as for 9th graders in the entire school district. Developmental transitions, particularly that into high school, are prominent issues about which educators should be concerned. Finally, the authors discuss practical implications for designing academic intervention and supplemental enrichment programs.