Although Guitar is several years older than Milkman – he was present at Mr. Smith’s suicide, which was the day before Milkman’s birth – the two become close friends during their teenage years. Guitar and Milkman create a male alliance that often stands in contrast with the female alliance of Pilate’s family. Initially, the two boys find peace and happiness in their interactions with Pilate, Hagar, and Reba; as Milkman puts it, he likes Pilate and her family, looks up to the “kind, wise” Guitar, and feels entirely comfortable in their mixed company. But as the novel progresses, both boys – now men – become increasingly separated from the loving community represented by Pilate and her family. The beginning of Guitar’s diverging path is marked by an important interaction he has with Railroad Tommy and Hospital Tommy, who, after listing to Guitar all the luxuries and happy things that he’ll never have due to his race, warn him that his life will be full of heartbreak and foolishness. The speech becomes a prophecy, and Guitar indeed finds himself on a tragic and violent journey. He becomes obsessed with seeking violent retribution for the atrocities that white people commit against Black Americans. Guitar has experienced his share of both personal and communal racial horrors. His father was killed in a factory accident caused by employer negligence, and the white owners show little care for their dead worker or the family he’s left behind. Guitar becomes increasingly radicalized by the murder of Emmett Till and the bombing of Birmingham Church, both real historical events that left innocent Black children dead at the hands of racist whites. Guitar joins up with a secret society called the Seven Days, which galvanizes young Black men to equalize the racial violence against Black people by killing one innocent white person for every innocent Black person.
Guitar’s anger – and his need for justice – is understandable. His pain, coupled with the pain of the greater Black community, is unbearable, and, predicting no end to the racism that pervades the United States at every level, Guitar sees vengeance as the only act that might give him purpose in an otherwise hopeless existence. Tragically, despite Guitar’s self-awareness – he tells Milkman early on that the Black community does “funny things” that hurt one another – he’s unable to apply this lucidity and wisdom to his own circumstances. Although his radicalization starts with him only targeting whites, he soon begins turning that violence against his own people, something he initially swore he’d never do. He convinces Milkman to help him rob Pilate to fund his latest mission, the murder of four white girls. Then, the search for money stains his relationship with Milkman, and, believing that Milkman has cheated him out of his share in gold, Guitar decides to hunt Milkman down and kill him. His cold-blooded chase results in him not only murdering Pilate, but likely ending both his and Milkman’s lives as well.
In many ways, Milkman’s greatest obstacles in his search for flight and liberation are other Black men like himself – namely, Guitar and his father. Both Guitar and Macon Dead have, in one way or another, severed themselves from their own humanity in order to cope with the unimaginable racial horrors and humiliations they have experienced. While Morrison grants a great deal of empathy to these characters, it’s clear that their chosen coping mechanisms do not benefit them, and in fact actively poison their souls, their futures, and their communities. Guitar was certain that the mission of Seven Days was reasonable, lacking in hate, and done out of love for Black people, and yet it results in Pilate’s death. Seven Days does not bring any good to Guitar’s life or the lives of his community. Aside from the fact that Guitar’s vision of justice was skewed and inhumane to begin with, he doesn’t even carry out his mission to kill the four white girls – all his preparation and devotion leads only to him destroying his own friends, Pilate and Milkman. Guitar does not achieve his goal of retribution. His vengeful actions do little to change the general racial landscape of America, and only increase the damage done to his own community.