Kennedy deftly peels back the layers of Whitney’s complex story to get to the truth at the core of what drove her, what inspired her, and what haunted her. He pulls the narrative apart into the key elements that informed her life—growing up in the famed Drinkard family; the two romantic relationships that shaped the entirety of her adult life, with Robyn Crawford and Bobby Brown; her fraught relationship to her own Blackness and the ways in which she was judged by the Black community; her drug and alcohol addiction; and, finally, the shame that she carried in her heart, which informed every facet of her life. Drawing on hundreds of sources, Kennedy takes readers back to a world in which someone like Whitney simply could not be, and explains in excruciating detail the ways in which her fame did not and could not protect her. In the time since her passing, the world and the way we view celebrity have changed dramatically. A sweeping look at Whitney’s life, Didn’t We Almost Have It All contextualizes her struggles against the backdrop of tabloid culture, audience consumption, mental health stigmas, and racial divisions in America.