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This study examines how philanthropic foundations and billionaire donors responded to the democratic threat posed by the ascent of Donald Trump in 2017, his illiberal reign, and the violent insurrection that he incited after losing his bid for reelection. The study incorporates both a large-n dataset of democracy-promotion grants by the nation’s top 1,000 foundations, as well as interviews and supporting materials from a sample of extremely wealthy individual philanthropists. The study embraces the view that concentrated wealth threatens democratic governance, while at the same time providing a theory of how (given the current state of the world) philanthropy might be channeled to provide a bulwark against an authoritarian government and/or shore up democratic norms and institutions.