An examination of decentralization and the devolution of authority for education to local school districts in the United States heighten attention to how superintendents mediate community social norms, interest group politics, and coalitions. Data from a nation-wide study are used to define the political dimensions of superintendent-school board relations. The Constitution of the United States of America reserved the right to provide education to individual states which created a decentralized system of education in the nation. The paper lays foundation by reviewing how the US education system is structured, governed and led (Björk, 2005). In addition it will provide a broad overview of the roles of superintendents before discussing literature related to their political role (Bjork, 2008). Literature on macro and micro politics will be used to analyze a superintendent’s political role in a implementing a district-wide school-based management system. Tension between centralization and decentralization emerge from a case study are examined and provide insight into the dynamics of devolving decision making from the school board, to middle managers to school-level. Findings suggest that middle-managers can support innovations as well as resist and even undermine change initiatives if their positions are threatened (Blase & Björk, 2010).