73 pages • 2-hour read
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Content Warning: This section of the guide includes discussion of sexual harassment, racism, antigay bias, substance use, and death.
In the first three parts of the novel, spanning from 1976 to 1979, Josey Wales is a top enforcer for Copenhagen City. He later forms his own gang, the Storm Posse, to manage his drug trafficking operations in New York. Josey is an antihero and the mastermind behind the ambush of the Singer. He plots the ambush to advance his ambitions within the hierarchy of the Kingston gang war, and also because he is fueled by resentment for the violence that has defined his whole life.
Josey has narrow eyes, leading many of his peers and witnesses to compare him to a Chinese man—a comparison intended to be a racist insult. He drives a white Datsun, which he uses during the ambush on the Singer. Josey is characterized as an educated and culturally literate character. He is both reflective and impulsive: While he often thinks about the meaning of his actions in retrospect and is deeply invested in symbolism and layers of interpretation, his rashness and short temper work against his better judgment. Josey’s rage causes him to massacre the crack house in Part 4, leading to his arrest and downfall at the end of the novel. Josey’s recklessness also causes him to ask Alex Pierce about the symbolism of shooting the Singer near the heart—a detail allows Alex and Tristan Phillips to realize that Josey was the Singer’s shooter.
Josey’s backstory is defined by the fall of the Balaclava tenement in 1966 at the behest of his boss, Papa-Lo, who loudly supported its demolition to claim the space for their gang stronghold, Copenhagen City. In the wake of Balaclava, Josey was shot nearly to death. This caused him to realize that gang violence will never end in Kingston and that he must take control of the entire city to ensure a peace that satisfies him. This ambition means knowing how to use the other power structures in Jamaica. In his quest, Josey both becomes a tool for the CIA—which enables his plans—and later forges a link with Doctor Love to undermine CIA agents Johnson and Clark.
Josey has a tense relationship with his boss, Don Papa-Lo. Although Papa-Lo is known for his ruthlessness, sometimes killing his own men when they defy his orders, he describes Josey as difficult to control. Josey, conversely, plots to overthrow Papa-Lo, first by planning the ambush on the Singer with Peter Nasser, Louis Johnson, and Doctor Love, and later by ordering Papa-Lo’s assassination at the hands of the police. In the latter case, Josey demonstrates his penchant for symbolism when he gets the press to report that 56 bullets were recovered from Papa-Lo’s killing, the same as the number of bullets fired at the Singer’s house. Josey intends the correspondence to indicate that the violence Papa-Lo instigated as Copenhagen City don, including the fall of Balaclava, created the circumstances that made the Singer’s ambush necessary.
The novel ends with Josey’s death, driving The Illusion of Ambition and Legacy as a theme. Although Josey manages to spin the failure of the Singer’s ambush to his advantage, he underestimates the ambition of his Bronx enforcer, Eubie Brown. Eubie plots the assassination of Josey’s longtime ally, Weeper, and claims responsibility for assassinating Josey as well. Josey tries to use his knowledge of this history to his advantage, but the threat of him turning informant also makes Josey a threat to everyone involved in drug trafficking in 1991. Josey thus becomes a victim of the same pattern of betrayal that allowed him to usurp Papa-Lo.
Nina Burgess is a young Jamaican woman whose brief encounters with the Singer and Josey Wales on the night of the ambush puts her into mortal danger. She spends the rest of the novel fleeing the worsening chaos in Jamaica and hiding from the vindictive and terrifying Josey; her experiences in New York City develop the theme of Diaspora and the Promise of Escape.
Although she is unemployed when the novel begins, Nina comes from a suburban middle-class family. Nina’s family has connections to upper class society, as evidenced by Nina’s sister Kimmy, who gets them access to a party thrown by the Singer’s record label. Nina and Kimmy compete for their parents’ affirmation. When Kimmy calls Nina in Part 2, she criticizes her for waiting outside the Singer’s house, believing that Nina wants to have sex with him. Nina accuses Kimmy of having double standards, but Kimmy gets her mother’s support by organizing an intervention for Nina. In reality, Nina is at the Singer’s house to leverage her past sexual relationship with him to get help with acquiring visas so her family can escape to Miami following a robbery at their house.
Nina is characterized as avoiding the news. She believes it is futile to learn about politics, which only confirms her sense that conditions are getting worse. During the ambush of the Singer, Nina has a face-to-face encounter with Josey, who threatens her and causes her to think that he will track her down and kill her as a witness. This changes the tenor of her political avoidance, which shifts from a desire to avoid the stress of current events to a desire to avoid reminding herself of Josey’s existence.
After fleeing Kingston, to protect herself from being found, Nina assumes a number of false names and identities over the course of a decade: Kim Clarke, the mistress of white American extractive industry worker Chuck; Dorcas Palmer, a caretaker for young children and the elderly, and Millicent Segree, a student nurse. Thematically, taking on these many identities prevents Nina from ever being her true self—a metaphorical commentary on the harm of self-effacing assimilation.
Nina’s romantic history reflects her shifting attitude towards her escape from Jamaica. In Jamaica, she uses her sexual desirability in transactional relationships. She wants to solicit the Singer to help her family flee Jamaica, a dynamic that recurs in her relationships with two American boyfriends, Danny and Chuck. When she reaches New York, she no longer needs to trade on her sexuality. Instead, her sexual identity becomes a measure of authenticity. First, she has a one-night-stand with a light-skinned Black man desperate to prove that he is Jamaican; however, he attempts to force her into having sex. Later, Ken Colthirst, an elderly man who becomes her client, encourages her to practice a different kind of authenticity: not to worry about being noticed in public because people forget one another after brief encounters.
Nina ends the novel on a positive note, reconsidering her distance from Jamaica. After the death of Josey, she approaches opportunities to reengage with her identity, such as talking to the wife of the injured Ranking Don, going to a Jamaican restaurant, and calling her sister for the first time since leaving.
Weeper is the right-hand man of Josey Wales through the first three parts of the novel. In Part 4, he enforces Josey’s drug trafficking operations in Manhattan and Brooklyn. This pits him against Josey’s Bronx enforcer, Eubie Brown, who becomes his rival for Josey’s approval.
Josey favors Weeper because of their compatibility as working partners. Josey describes Weeper as intimidating, and someone Josey can understand through his eyes. Weeper wears glasses, which remain cracked after being broken in incarceration. Like Josey, Weeper is an educated man; he is an atheist, having studied the work of British philosopher Bertrand Russell during his incarceration.
Weeper is bisexual, having sexual encounters with both women and men throughout the novel. His exploration of his sexuality is a major element of his character arc, beginning with a romantic relationship with another man during Weeper’s incarceration. Josey disapproves of Weeper’s queerness. When Weeper moves to New York, he feels that he has escaped Josey’s oversight, allowing him to explore his sexuality with greater agency and discretion. In Part 4, this results in a relationship with the blonde man who distracts Weeper from his duties before Josey’s arrival in the city. Weeper assures himself that being in New York means that he can do anything he wants, playing into the idea of diaspora and the promise of escape.
Weeper is assassinated by hitman John-John K as part of Eubie’s elaborate plot to unseat Josey as the head of the Storm Posse. First, Eubie paints Weeper as an incompetent enforcer in a bid to replace him as Josey’s right-hand man. Simultaneously, Eubie pledges loyalty to drug kingpin Griselda Blanco in exchange for her help with Weeper’s murder. During his last moments, Weeper connects with John-John over their shared loneliness as queer people. He tricks John-John into letting him freebase pure cocaine, which allows him to die by overdose. This causes Josey to doubt whether Weeper was assassinated, allowing for the possibility that he died either by accident or by suicide.
Alex Pierce is an American journalist uncovering the truth about the Singer’s ambush. He comes closest to providing an objective narrative of the event, though its details are eventually manipulated by Eubie to aid his ascent to power.
Alex first comes to Kingston as a reporter for Rolling Stone magazine. He disregards his official assignment to cover British musician Mick Jagger’s activities in Jamaica because he intuits that something bigger is brewing in Kingston. Like Papa-Lo and CIA station chief Barry Diflorio, Alex connects the violence in Kingston to the Singer’s upcoming concert and comes close to predicting the Singer’s ambush. Despite his proximity to the Singer’s house when the ambush begins, he abandons his lead and doesn’t witness the event. Alex’s tendency to come close to the real story but miss out on the crucial detail is a recurring character trait.
In the succeeding years, Alex becomes increasingly obsessed with writing about the Singer’s ambush and the gang war connection. He interviews each major gang don and is eventually forced into an interview with Josey Wales, in which he accidentally learns that Josey shot the Singer by connecting a forensic detail about the Singer’s ambush to one of Josey’s statements—a revelation he has years later, when he is interviewing Ranking Dons member Tristan Phillips. Alex eventually publishes a seven-part report on Josey’s massacre of a Bushwick crack house, forgetting Tristan’s advice to wait until all the parties involved in the story have died. This story becomes a metafictional element in the novel, as commentary about its completeness, contradictions, and effectiveness reflect James’s own novel about the same material. Alex’s reportage is largely ignored by the public; however, its subjects take an intense interest in how Alex presents events. Eubie comes after Alex, torturing him into downplaying Josey’s role in the Storm Posse. When Alex reveals his knowledge about Josey’s role in the ambush, both Tristan and Eubie are impressed and encourage him to continue writing the “official” narrative of the ambush.



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