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This paper reimagines and re-engages Robert Dahl’s central assumptions in Who Governs? Democracy and Power in an American City. In the ensuing decades since the writing of Who Governs?, the political landscape has changed dramatically with regard to voting turnout, the robustness of the local media, the decline of group participation in civil society, and the concentration of wealth (and power) as well as two unforeseen developments: the covid pandemic and the rise of Trumpian politics. In addition to the changed political landscape, municipalities face serious and intractable policy issues as well as a diverse and more powerful set of political players. This paper will look at a small upstate river city, Kingston, NY, which was once the capital of New York State. What happens when Kingston city officials seek to sell public water rights in order to redress aging infrastructure? To what degree should a local philanthropist’s money dictate solutions to public problems without democratic accountability? Should we extend marginal payments in lieu of costlier taxes (also known as Payment in Lieu of Taxes or PILOTS) to private real estate developers as a way to resolve affordable housing issues? These issues tell us not only about the political terrain in Kingston, NY but also about the challenges to municipalities and democratic politics around the globe.