One of the most consistently reported challenges in education is the underachievement of African American males at all levels of education. African American boys are falling behind and they are falling behind early. Parental involvement in the home and at school can promote academic success through a number of mechanisms: parental involvement in school activities, expectations that parents share with their sons and for which they hold them accountable, and parental trust and support for both their sons and their sons’ schools. This study demonstrates the importance of relationships that promote trust and high expectations in fostering academic success in African American boys. The consistency of positive home structural factors contributed to the academic success in the families studied in spite of negative factors such as divorce, economic deprivation, parental unemployment, previous parental incarceration and lack of transportation.