When and how did Barack Obama's now well-known “hope” mantra take shape? Carpio's essay explores this question through close readings of key passages from Obama's autobiography. It is nearly three hundred pages into the autobiography before the phrase “the audacity of hope” appears, at the end of the “Chicago” section. Obama has just been accepted to Harvard Law School and has yet to take his first trip to Africa to find his paternal family when he hears the phrase from his infamous ex-pastor, Jeremiah Wright. The essay places this moment from the “Chicago” section in the context of the entire autobiography to illuminate why, for Obama, it takes audacity to hope that we can transcend America's history of racial conflict. In the process, the essay reveals Obama's dark view of race relations in America before he became the symbol of a supposedly post-racial America that he is now.