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Abstract Background Childhood poverty is known to be associated with poor health. For youth living in extreme poverty, community-based programs focused on youth development are one strategy to improve health and well-being outcomes. However, very few evaluations of the long-term effectiveness of youth development programs have been conducted. The aim of this study was to assess the long-term effectiveness of a positive youth development program (PYD), serving a segregated housing project with a history of community violence, to improve the health, education, and financial well-being of its alumni. Methods A quasi-experimental causal comparative study design was used to study the effectiveness of the Cabrini-Green Youth Program (CGYP). CGYP alumni (mean: 16.8 +/- 7.4 years after program participation) were surveyed. For comparison, participants from the same housing project who were eligible to participate in the CGYP but did not, were identified. Results In total, 246/417 (59%) eligible alumni were located. 221 alumni were available to be interviewed; 191/221 (86%) completed the interview survey along with 143 in the comparison group. Both groups self-identified as being Black, African American, and of Other race. Alumni were younger (34.6 vs. 38.1 years, p