In the late twentieth and early twenty-first centuries, and despite wide-scale technological disruption of the journalism business, publication of high-quality non-fiction sports books rapidly expanded (Kuper, How Books About Sport Got Serious. Financial Times, 2013). The book form enables ‘thick’ investigation of complex narratives; authors have space to reveal hidden stories previously untouched by news outlets. H.G. Bissinger’s Friday Night Lights: A Town, A Team and A Dream (1990) and Michael Lewis’ Moneyball: The Art of Winning an Unfair Game (2003) represent the commercial and stylistic high points of the boom in sports publishing in the US and pointed towards a radically different future for literary sports journalism. The former book, an example of New Journalism, highlighted what sport, specifically high school American football, could tell us about American politics and society. The latter explored what data and performance analysis could tell us about how professional sport conducts its business on the field. Friday Night Lights arguably signified the end of the New Journalism era while Moneyball signalled a data-driven future. Both books are considered, through textual analysis, for their contributions to literary sports journalism. The chapter concludes by considering what their transfer to film and television tells us about transmedia storytelling (Jenkins, Transmedia Storytelling. MIT Technology Review, 2003) and what this might mean for the future of literary sports journalism considered in subsequent chapters.