This qualitative case study explores the political and leadership challenges imbedded within the implementation of a district-wide resource reallocation policy. Based on a two-year study of a medium-sized district's efforts to address changing demographics of families in the district and a widening achievement gap, we draw upon concepts from education finance and the politics of policymaking to better understand the strategies used to introduce and implement a differential resource-allocation formula. Leadership strategies are explored, with a focus on anticipated areas of both internal and external "pushback," and a discussion of the cycle of political support for equity-focused policy initiatives.