After years of decay, Baltimore City’s urban poor face disparities within an economic and political climate that demands austerity and personal responsibility. This qualitative research project aimed to identify the impact of deindustrialization on the socioeconomic changes within the community, the subsequent disparate incarceration rates, and burden on affected individuals, communities, and organizations. We also theorized the best practices for advocacy and community organizing. The findings suggest that in many communities, the nature of social capital has transformed in relation to local and national processes, such as recession, unemployment, declines in industries, and exposure to surveillance. Though fragile, the existing community cultural and social capitals, networks critical to family functioning and daily survival, must be reappraised and integrated in participatory collaboration with stakeholders. Traditional community organizing tools must be re-examined and reframed to reach larger audiences and to build alliances.