The cases are the two separate jurisdictions of the City of San Bernardino and the County of San Bernardino, California, U.S.A. The matched pair offers a unique opportunity for a research design that compares a bankrupt city government with a jurisdiction sharing the essential demographic, economic, and geographical features, though as a county a different level of government. The two cases offer insights into bankruptcy as not simply a function of economic forces or recent poor policy choices but as a result of a pattern of decision-making, a structure of government, and the constraints placed on leadership by structure and electoral politics. The analysis of this comparison allows us to unbundle leadership and show that differences in strategy, transparency, civic culture, trust and accountability explain the divergent outcomes.