Starting out from an analysis of the “Art of the Deal,” this paper seeks to understand Trump’s “deal-making” as a form of life under capitalism organized around the paradoxical desire to simultaneously “be the game” and be the “biggest winner”— In this way, Trump exemplifies a modern pathological form of existence whose proximate roots can be found in German idealism, and perhaps most clearly in Fichte’s Closed Commercial State. Here Fichte proposes a wage to end all wagers; a monetary operation that would put the entire world on the path to world peace and economic justice. Fichte’s economic nationalism—- world peace is only possible by the complete closure of the state as commercial entity— is the very opposite of what is now spoken under that name; and yet the desire to “play the game” and “master it” at the same time offers a point of commonality. Beyond the scope of this paper lies the questions: is this paradoxical desire ultimately theology in origin? Is another relation to contingency possible?