Malcolm takes on a variety of odd jobs in Harlem. For six months he transports betting slips for the numbers lottery system. Then, after working in a gambling parlor, Malcolm works for a madam, steering white people from downtown to the various places where their elaborate sexual fantasies can be fulfilled. In 1945 Malcolm is accused of robbing a craps game run by Italian racketeers. He begins to feel tense just walking the streets of Harlem. He quits his steering job and begins importing bootlegged liquor from Long Island for a Jewish businessman. He likes the work and his boss, but his boss disappears mysteriously after a scandal involving the bootlegging.
Malcolm himself plays the numbers more and more heavily, placing bets with West Indian Archie, an “old head” known for his photographic memory, which enables him not to have to write down any of the bets he takes. Malcolm hits a low point when West Indian Archie accuses him of collecting winnings on a bet he had not actually placed. Malcolm insists he has remembered correctly, and according to the code of the street, neither can back down. West Indian Archie gives Malcolm until the next day to return the money. Malcolm gets high on various drugs and wakes up long after the deadline. He returns to Harlem, where he runs into West Indian Archie at a bar. West Indian Archie humiliates Malcolm but does not shoot him, and a confrontation looms. The next day Malcolm punches a young hustler in the face, is almost stabbed, and is searched by the police. Now the cops, the Italian racketeers, the hustler Malcolm has just punched, and West Indian Archie are all out for Malcolm’s blood, and he feels more threatened than ever. Just as Malcolm thinks he is going to get shot, Shorty picks him up and takes him to Boston.
In Boston, Shorty and Ella marvel at the transformed Malcolm, now edgy and foulmouthed from hustling. Malcolm takes a few weeks to unwind from the tension of his situation in Harlem, at first only sleeping, smoking marijuana, and playing records. Malcolm begins to do cocaine again and talks excessively to Shorty and Sophia about future plans. He remains close to Sophia, depending on her for money and marveling at how much abuse she takes. Sophia’s husband is often on the road on business, which enables Malcolm to see a lot of Sophia. Shorty begins seeing Sophia’s seventeen-year-old sister.
To make ends meet, Malcolm decides to find a new hustle. Using his reputation as ruthless and trigger-happy, he puts together a burglary ring consisting of himself, Shorty, and a local black Italian man named Rudy. They include Sophia and her sister to scope out white neighborhoods without arousing suspicion. Usually, the women visit a home as pollsters or salespeople and entice the housewife to give a tour. They then describe what they see in the house to the men, who go to the house at night. Shorty and Malcolm do the actual burglary, while Rudy mans the getaway car.
One day, while high on cocaine, Malcolm sees Sophia and her sister in a black bar with a white man who is a friend of Sophia’s husband. Malcolm saunters over and addresses the women intimately, blowing Sophia’s cover. The friend and then Sophia’s husband himself later go on the hunt for him. When police arrest Malcolm in a pawn shop, he gives himself up peacefully. In court his conviction for stealing is due as much to his relationship with a white woman as it is to his burglary. Malcolm notes that the police cross-examine him on the origin and nature of his relationships with the women instead of on the crime of burglary with which he is charged. The judge sentences him to ten years in state prison.
In these chapters, Malcolm shows us the depths to which he sinks in Harlem so that we can understand the dramatic nature of the education and conversion he subsequently undergoes in prison. His statement that “[a]ll of our experiences fuse into our personality” reflects his belief that he must understand his past to understand his present. Malcolm’s education allows him to reevaluate the forms of racism he experienced earlier in his life. Whereas before his time in prison he responds to individual encounters of prejudice as separate instances of personal attacks, his new, more fully developed perspective on race relations leads him to see them as part of a single problem. His conversion to Islam similarly leads him to a more expanded understanding of racial problems. He now understands them on both a national and international level: white America has mistreated black America from slavery through segregation, and Western societies have historically used and abused nonwhites. Just as his conversion to Islam offers him the possibility of redemption under Allah, his process of self-discovery offers him the possibility of a more productive, though still limited, place in society.