In this article we describe and analyze the challenges faced by an intervention program that addresses the fatherhood needs of low-income urban African American males. We used life history as the primary research strategy for a qualitative evaluation of a program we refer to as the Healthy Men in Healthy Families Program to better understand the circumstances and trajectory of men's lives, including how involement in the program might have benefitted them in the pursuit of their fatherhood goals. A model of masculine transformation, developed by Whitehead, was used to interpret changes in manhood.fatherhood attitudes and behaviors that might be associated with the intervention. We combined Whitehead's model with a social ecology framework to further interpret challenges at intrapersonal, interpersonal, community, and broader societal levels.