The Award Winner and Other Stories explores the question of success within the African-American community and the moral, ethical and personal sacrifices made by some to attain it. Three of the stories follow one young girl, Josie, in particular as she jostles between cultures and worlds, integrating a predominantly white private school, visiting an all-black summer enclave and attending an Ivy League school. Issues of race, class and gender influence her even as she searches (with varying degrees of success) for personal meaning and agency. Other characters wrestle with the burden of being pioneers, of carrying the weight of a race's (still somewhat questioned) potential while facing their own personal concerns, wants and needs. In a country where the "pursuit of happiness" is written into its very DNA, these struggles reflect the ever increasing weight and complexity of the "American Dream'-- it's at once persistent elusiveness and heady promise.