In management and organization studies, the challenge of dealing with paradoxes has become a central issue. The literature, however, is largely populated by research inclined to idealize paradoxical framing in thinking and theorizing. In this paper, we explore the perils paradoxes present when generated by stretch goals the 'achievement' of which is accomplished through organizational charade. The Volkswagen (VW) emissions scandal is a case that shows how paradoxical promises that are embraced discursively but not substantively create representational simulacra rather than paradoxical mastery. By studying VW's attempt to embrace paradoxes that proved to be a stretch too far, we explore how hubristic leadership, embedded in high-level cultural intolerance for failure, initiated VW's scandal.