Every year, professional basketball franchises convene for an entry draft to select the next generation of talent for their respective teams. This article describes an experiential exercise that places students in the role of team executives of a fictionalized professional basketball franchise. Students are tasked with evaluating a group of draft-eligible athletes and making the optimal selection for their team, considering a wide array of skills, abilities, and attributes. The Basketball Draft Night Exercise is informed by extensive research on sport entry drafts spanning several decades and sheds light on the systematic errors, fallacies, and decision-making biases that arise when making talent selections under uncertainty. Furthermore, this exercise illuminates the potential pitfalls and cognitive errors committed by experts when assessing and selecting talent under uncertainty.