As New Orleans becomes an important reform model worldwide, many have been attracted to the simplistic logic of decentralized, market-based educational reforms that assume easily articulated and quantified goals and rational actors. In an effort to reclaim a role for social justice in such an environment, this chapter assumes the position that educational leadership for social justice must prioritize community engagement, indeed community leadership, if it is to be both sustainable and just. Guided by scholarship on the ethic of community (Furman, J Educ Adm, 42, 215–235, 2004; Furman and Shields, How can educational leaders promote and support social justice and democratic community in schools? Paper presented at the American Educational Research Association, Chicago, 2003; Shields and Seltzer, Educ Adm Q, 33, 413–439, 1997), it begins with a history of the Morris Jeff Community School, followed by a series of cantankerous contradictions which highlight points of conflict between community leadership and many features of the currently popular market-based reforms (heroic vs. democratic leadership, competition vs. systemic improvement, state vs. localized goals, and teacher leadership vs. teacher churn). The analysis concludes that urban schools need leaders with expertise rather than expertism and that the development of adult leadership within our urban communities may provide the best hope of reconnecting social justice to the work of educational leaders.