The Delaware River Basin (DRB) in the Mid-Atlantic region of the United States is an institutionally complex water resources system that provides drinking water for 13.5 million people, plus water for energy, industry, recreation, and ecosystems. This paper introduces Pywr-DRB, an open-source Python model exploring the impacts of reservoir operations, transbasin diversions, and minimum flow targets on water availability and drought risk in the DRB. Pywr-DRB draws on streamflow estimates from emerging data resources, bridging advances in large-scale hydrologic modeling with an improved representation of the basin's evolving water infrastructure and management institutions. Our detailed model diagnostic assessment demonstrates that Pywr-DRB provides substantial improvements over sole use of hydrologic models in capturing the DRB's dynamics. We also explore how water management alters model-derived risk estimates for low flows and water demand shortfalls. Our approach to diagnostic benchmarking and water systems modeling is broadly applicable to other major basins.