This research presents the qualitative case study of an urban community school initiative that began as an educational reform effort and that ultimately failed. The process of emergence for this school and factors leading to its collapse are described through participant interviews and document analysis. Nationally, policy reformers, practitioners, and the public have been seeking solutions to urban education challenges. With this attention and the appropriation of government funding, a multitude of unique UCS initiatives run under a broad variety of auspices, are emerging. Currently, there is a lack comprehensive regulation and data examining the overall success of community schools. This study explores challenges associated with this type of educational reform. The research findings provide lessons-learned and key components to build upon for successful future initiatives and cautions regarding the actions that led to failure for this UCS. It exemplifies the need for a critical analysis of a community's social and cultural capital before an initiative emerges. These findings suggest the importance of emphasizing 1) focus on a substantial planning period which embraces members of the community in equitable roles, 2) proper funding and financial sustainability in place, and 3) a cultivation of understanding that addresses cultural and class disconnections. Community schools appear to play a role in the ability to positively change urban students' holistic outcomes.