Malcolm's brief relationship with the Hill girl Laura represents his last contact with the sort of "respectability" toward which Ella encouraged him. And his jilting of Laura for the white woman Sophia is perhaps the major turning-point of his life in Boston. Laura, bright, ambitious and from the middle class, represents the world Malcolm rejects in favor of the ghetto; and Sophia, his white girl friend, is a symbol of his success in the world of hipsters and hustlers. Rather than adjusting himself to Laura's world, Malcolm brings her into his.
To Malcolm, Laura seemed different from the other Hill girls, whom he by now despised; she was serious and quiet, and seemed less snobbish than the other girls. She was a good student and planned to go to college. She tried to encourage Malcolm to continue his education, but, of course, he paid no attention. She told him there was no reason why he couldn't become a lawyer, despite Mr. Ostrowski's advice; by now, however, Malcolm's goals had changed entirely.
Malcolm took Laura to dances at Roseland, against her grandmother's wishes, and in giving her a taste of ghetto life, he led her to her own destruction. After he jilted her, she began drinking and taking drugs, and finally became a prostitute. But by this time Malcolm had lost interest in her — because of Sophia. In contrast to Laura, Sophia was fair and blonde, and well-dressed — the sort of woman who was a real status symbol in the ghetto. Consequently, as Malcolm began to be seen regularly around Roxbury with Sophia, his status rose quickly. His newfound popularity was due partially to the fact that he was a man who could have a white woman who wasn't a prostitute, and even had her own car; also, Malcolm was envied by the other hipsters. Laura was totally forgotten.
In retrospect, Malcolm blames his involvement with Sophia on being "brainwashed" by the whites; otherwise, he would not have considered such a woman as desirable. Still, his affair with her lasted for five years and was the only long-lasting relationship with a woman he had before he met the woman he was to marry, several years later.
When America entered World War II, there was a shortage of help on the railroads. Ella seized this opportunity to get Malcolm a job as a dishwasher in order to lure him away from Sophia. Ella's scheme did not work; Malcolm and Sophia continued to see one another. But the job on the railroad introduced Malcolm to Harlem, which was to become his real home. Harlem was a new experience for him; it was as different from Roxbury as Roxbury had been from Lansing. Malcolm knew he could never be truly content living anywhere else.
Malcolm's wild manner got him fired from two successive railroad jobs, but eventually he found work as a waiter at Small's Paradise, one of the most famous nightclubs in Harlem. From other workers at Small's, and from the customers, Malcolm began to learn about Harlem. They told him about one white ethnic group repeatedly replacing another in that section of the city — until, finally, the blacks began moving in and drove out the last of the whites. They told him about the twenties, when Harlem had the best-known night spots in New York. But mostly he learned from the customers, many of whom were professional criminals, about the various rackets going on in the city — the numbers, pimping, selling drugs, and robbery. This information was to prove very useful to him.
In Chapter Six, Malcolm describes the Harlem underworld and how he finally became a part of it after being fired from Small's. The chapter opens with a discussion of the numbers racket, which the white gangsters called "the nigger pool" because most of the players were blacks. It was a well-organized racket but based upon a very simple operation. The "numbers" are the last three figures of the daily total U.S. domestic and foreign sales; the goal is to guess these numbers. The odds against doing so are one thousand to one, and a "hit" pays off at six hundred to one. So the bettor stands to make a large profit, but those who operate the racket make a tremendous profit. It is a game of pure chance and that is one of its main attractions: because no skill is involved, anyone can win at it (though few actually do).
Through his job as a waiter at Small's, Malcolm became acquainted with many of Harlem's top underworld figures, and some of them began to take an interest in him and to re-educate him as a hustler. It was also in Small's that Malcolm began to learn to identify undercover police officers, first by having customers point them out, then by developing the ability to sense that someone was a detective. This "sixth sense" was a necessity for a successful hustler.
There was an air of genuine friendship and solidarity among the underworld characters who hung out around Small's. There was a sense that, although the hustlers were all in competition with one another, they were all victims of the white man's culture and had to help fellow-victims who were down and out.
Sophia occasionally came to New York to visit Malcolm. Even among the most sophisticated Harlem blacks, she attracted attention and made Malcolm feel important. During this time, she married a wealthy white Bostonian, but this did not alter her relationship with Malcolm. A pimp named Sammy, Malcolm's best friend in Harlem, warned Malcolm that this might happen. Sammy attributed the attraction of the white woman to the black man to the woman's being "in love with lust": the black man represented a forbidden pleasure, more exciting because it was forbidden. Malcolm realized that there could be no real love in such a situation, but he was content to continue the relationship on those terms.
When Malcolm was fired from Small's, Sammy set him up in business peddling marijuana. Soon he was under police surveillance and had to leave New York for a time; shortly thereafter, he devised a scheme to follow touring musicians, using his railroad pass, and supply them with marijuana. For several months he was a "travelling hustler," safely out of reach of the New York police. He was launched upon a career in crime which would end only with his arrest four years later.
Malcolm's tour on the railroad ended abruptly after he threatened a railroad cook with his pistol during a card game. He could not return to selling drugs because the narcotics squad knew him. So for his remaining two years in New York he was involved in a number of different hustles and rackets — robberies, numbers, gambling, bootlegging and prostitution. During this time, the hazards of his job increased with his reputation, and he began to make enemies.
During the months after he was forced to quit travelling, Malcolm began to pull his first stickups. Like most professional holdup men, he began to use hard drugs to strengthen his nerves; before long he was addicted and stayed high most of the time.
Reginald was now in the merchant marine, and the second time he came to visit Malcolm in Harlem, Malcolm persuaded him to go AWOL and stay. Malcolm found him a safe, easy hustle — selling watches, jewelry, and other such items as if they were stolen goods, when actually they were imperfect merchandise bought at cut rates. There was nothing illegal about it, but the appearance of illegality made it a thriving business.
Eventually, Reginald drifted away from Malcolm, and his friendship with Sammy was disrupted by an argument. Malcolm was thus on his own again. He got a job as a numbers runner, carrying slips of paper back and forth. He also began to play the numbers with one of the most important runners, West Indian Archie. Even after he moved on to other jobs, Malcolm continued to do business with Archie; and it was Archie who eventually drove Malcolm out of Harlem — because of a misunderstanding.
Malcolm worked for a time as a "steerer" for a house of prostitution, where he learned more about the immorality of whites and more about the perversity of interracial sex. This job ended abruptly when he came under suspicion in a liquor store robbery. He quit his job and went to Michigan to visit his family. When he returned, he worked for a Jewish bootlegger. About this time, he again was falsely suspected of robbery. He escaped the men sent after him, but later the same day, Sammy told him that West Indian Archie had been looking for him. Malcolm had "hit" on a fifty-cent bet, and earlier that day Archie had paid him three hundred dollars out of his own pocket. Malcolm wasn't worried about Archie at the time and didn't change his plans to go out that evening. But circumstances were closing in on him; and he says Allah must have been watching over him to save him.