This essay explores political and aesthetic 'failure' in the work of William Gaddis, specifically arguing that failure was his critical response to the triumphalism of an emerging neo-liberalism. In the first half I argue that Gaddis drew on Norbert Wiener's 1950 The Human Use of Human Beings: Cybernetics and Society as a 'sourcebook' for his novel JR because it offered a critical counter-point to an increasingly hegemonic positivism. I specifically explore the parallels and divergences between the work of Wiener and his erstwhile colleague Milton Friedman to suggest that Wiener provided Gaddis with a formal and methodological alternative to the modelling of conservative economics. The second half of the article focuses on JR, drawing out the ways in which the novel draws on Wiener in order to make evident the importance of failure as a site of political and aesthetic critique. In this section I highlight how the 'difficult' formal properties of the novel offer their own parodic response to an empirical methodology: as they force us to question what it is that we know we know in an entirely different way.