Decentralization and deregulation policies assume that local educational leaders make better resource decisions than state policy makers do. Conceptual models drawn from organizational theory, however, offer competing predictions about how district central office administrators are likely to leverage their professional expertise in devolved decision making about school funding. To explore deregulation policy in practice, I examine resource decision making in two urban school districts using the case of a 2009 California school funding deregulation policy. I argue that expertise is a key political dynamic in district resource decision making, setting the framework by which decision makers interpret and weigh local school quality, cost, and equity concerns and, as a result, reallocate deregulated dollars.