Walter Benjamin's warning against unphilosophical “astonishment that the things we are experiencing are ‘still’ possible” has new urgency in the face of real estate developer and reality-show host Donald Trump's surprise victory in the presidential election of 2016. Philosopher, sociologist, and cultural theorist Georg Simmel's 1900 magnum opus, the Philosophy of Money, provides valuable orientation at a moment when the expectation that public discourse must be oriented by norms of truth and accuracy is under siege—not least by those who ascended to power openly denigrating the value of expertise and the specialized knowledge long regarded as essential to modern government. Trump has an instinctive grasp of Simmel's decisive insight that “money is the strongest and most immediate symbol” of the cynical truism that “the only absolute is the relativity of things.” Situating philosophy at the limits of disciplinary ways of knowing, the Philosophy of Money develops a modernist, performative strategy of thought that turns relativity into a philosophical resource. It can help us to counter the dissolution of the ideal of veracity in an era of absolutized marketing by disentangling thought from narratives of rational progress that obscure its opposite and interrogating the limitations of the professionalized ordering of knowledge practices in which expertise continues to be produced and maintained. Simmel's strategy for embracing the fragmentation, multiplicity, and uncertainty of human experience may thereby help us address the complexity and ambiguity of a historical situation growing increasingly surreal as techno-scientific progress goes hand in hand with post-truth politics.