The objective of this study was to explore the career narratives of professional athletes from underserved communities in the United States. Two African American athletes (named Marcus and Imari for the study), who both met the criteria of playing at least one year in a professional league and spending their formative years in an underserved community, participated in this study. Life story interviews lasting about two hours were explored through the principles of narrative analysis, focusing on both content and structure. Each participant constructed a sink or swim narrative typology termed risk, descent, and gain that focused more on the environmental context in an underserved community than their athletic development, which opposes the performance narrative often depicted by professional athletes. Although the contextualised nature of risk manifested differently for Marcus and Imari, their life courses both reflected low points precipitated by risky decisions or circumstances followed by gainful moments ultimately culminating in professional contracts. The analysis also uncovered the realities and challenges associated with having the intersecting identity of being a poor, Black aspiring athlete in a racially charged atmosphere. Finally, the athletes’ perceptions of how their challenging formative development influenced their professional career pathway as well as the ramifications of sink or swim narratives in popular American culture are considered. © 2020, © 2020 Informa UK Limited, trading as Taylor & Francis Group.