This paper addresses the fundamental question: What price is society prepared to pay for the fictional fabrication of the cultural hero-system of sport? Based on a critical analysis of selected literary works by John Updike, Irwin Shaw, and Jason Miller, this paper argues that the existential crises from which character emerges in these accounts reveal the cultural hero-system of sport to be regressive. In particular, this paper argues that sport offers a world of social, moral, and emotional simplicity, a world focused on the themes of youth, and that as a cultural hero-system sport can, at worst, infantilize those who seek to derive sense and meaning from it.