Fifteen residents , formerly of the streets and/or criminal justice system, were organized into a street participatory action research team to conduct a street ethnographic community needs assessment of the Eastside and Southbridge neighborhoods of Wilmington, Delaware. This article is primarily a qualitative analysis of the educational and employment experiences of a community sample of street identified Black men and women between the ages of 18-35. This secondary analysis is guided by the question: How do street-identified Black men and women frame their experiences with educational and employment opportunity? Mixed methods were employed to collect data in the form of: (1) 520 surveys; (2) 24 individual interviews; (3) four dual interviews; (4) three group interviews; and (5) extensive ethnographic field observations. All data were collected in the actual streets of Wilmington, Delaware (e.g., street corners, local parks, barbershops, local record/DVD stores, etc.). Two core themes emerged in qualitative coding for schooling opportunity, which include institutional removal and student-teacher interactions. Also, three subcodes emerged out of the student-teacher interactions theme: (1) lack of academic preparation, (2) lack of cultural competency, and (3) home/neighborhood conditions related to schooling experiences. Further, two subcodes emerged for the core theme employment: (1) neighborhood isolation and (2) employment after incarceration.