Englewood is a Chicago neighborhood known widely for its violence, but significantly less so for its rich culture of community organizing. In order to better understand Englewood, identify its struggles and successes, and formulate thoughtful policy solutions, this paper uses qualitative interviews, ethnographic fieldwork, and document analysis to provide an account of Englewood today through residents’ eyes. This develops a cyclical understanding of how disinvestment contributes to poverty and violence, and how investment helps re-establish Englewood as a thriving community. Interviewees believed negative “place tropes” adversely impact the neighborhood, but also shared stories of hope and growth. Developing this complex understanding of Englewood helps to combat harmful stereotypes and guide analyses of how policies to improve areas like Englewood can succeed through community insight and support. These policy recommendations are gathered together through a shared theme: combating disinvestment and hopelessness by investing in Englewood, recognizing community successes, and addressing continuing inequities.