The interface between legislative oversight and implementation processes under structural-devolution reforms is rarely studied. Drawing on qualitative data from county governance in Kenya, this study establishes collective action problems to legislative oversight characterized by shaky alliances between legislatures and administrative executives in budget-maximization, poor role-conception of legislative activities, little electoral connectivity and parochial rather than institutional interpretations of political-representation. Similarly, priorities for political profitability of oversight and patronizing structures of political parties override political-administrative controls in local governance. It is thus concluded that democratic reforms through structural-devolution tend to sophisticate legislative oversight by aggravating institutional inconsistencies and political-administrative trade-offs at both levels of government.