Simone C. Drake spent the first several decades of her life learning how to love and protect herself, a black woman, from the systems designed to facilitate her harm and marginalization. But when she gave birth to the first of her three sons, she quickly learned that black boys would need protection from these very same systems—systems dead set on the static, homogenous representations of black masculinity perpetuated in the media and our cultural discourse. In When We Imagine Grace, Drake borrows from Toni Morrison’s Beloved to bring imagination to the center of black masculinity studies—allowing individual black men to exempt themselves and their fates from a hateful, ignorant society and open themselves up as active agents at the center of their own stories. Against a backdrop of crisis, Drake brings forth the narratives of black men who have imagined grace for themselves. We meet African American cowboy, Nat Love, and Drake’s own grandfather, who served in the first black military unit to fight in World War II. Synthesizing black feminist and black masculinity studies, Drake analyzes black fathers and daughters, the valorization of black criminals, the black entrepreneurial pursuits of Marcus Garvey, Berry Gordy, and Jay-Z, and the denigration and celebration of gay black men: Cornelius Eady, Antoine Dodson, and Kehinde Wiley. With a powerful command of its subjects and a passionate dedication to hope, When We Imagine Grace gives us a new way of seeing and knowing black masculinity—sophisticated in concept and bracingly vivid in telling.