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Chapters 5,6,7, & 8
All through this phase he kept in touch with Sophia, who used to come from Boston to meet him. Initially she was a bit worried about the prostitutes staying near Malcolm's apartment. However, all her fears were put to rest when Malcolm introduced his prostitute friends to her.
At Ed Small's Bar, Malcolm would sometimes give the phone numbers of the prostitutes to customers who were interested. Once he got into trouble while giving a contact number to a customer. The customer was an army man. He readily accepted the number. But never went to the address given. When Malcolm discovered that the customer never got in touch with his friends he realized that he would soon be grabbed by the police for 'impairing the morals' of a service man.
It turned out that the army man was a military spy. Very soon, Joe Baker, a plain-clothed detective arrived at the Bar, where he was arrested and taken to the police station. Malcolm was let off lightly. This is because he had never had any trouble with the police previously.
Ed Small refused to hire him back for he now had a police record, but that did not hurt him so much. What hurt him more was that he was also barred from entering the bar. Now jobless and without a friend, Malcolm sought advice from Sammy, a pimp. On Sammy's advice, Malcolm begins to peddle marijuana. Soon, he is on the 'wanted' list of the Police Narcotics Department. Malcolm began carrying a pistol for protection. He also used several tricks to hide his drugs and even hood wink the police.
He realizes that the situation is becoming rather hot for him in New York. Sammy suggests that he use his rail road identification (which he still carried) to get a job for a while until things cool down. Following Sammy's suggestion, he leaves New York and follows his musician friends with the help of his railroad pass. During his railroad trips, he sold drugs and 'reefers' to the customers (who mainly consisted of his musician friends that he had made on his first job as a shoeshine boy). His travels on the railroad ends when he threatens a cook on the train with his pistol during a game of cards.
Malcolm could not get back to peddling drugs because the police was still on the look out for him in New York. So he started "hustling" or betting on numbers, which he had learned while working at Small's bar. He also began doing small robberies and later boot-legging (for a short while) for a Jew called Hymie. During this period he became addicted to drugs. Malcolm had begun to live dangerously. He also made enemies among his hustling circle partly due to his temperament and partly out of some misunderstandings.
Malcolm recalls one such incident, which occurs with West Indian Archie. West Indian Archie is a huge black man, who is also in the hustling business. A fight breaks out between West Indian Archie and Malcolm. Archie thinks that Malcolm has cheated him on some money used in the hustle game. So Archie is looking for him to get revenge. At one meeting the two almost kill each other. The entry of a cop at the moment makes them flee. Besides West Indian Archie, there is Sammy who also turns against him. In one incident, Sammy would have shot Malcolm if his girl friend (Sammy's) had not intervened. Sammy was annoyed because Malcolm had been rude to his girl.
Malcolm quits working for Sammy and starts work as a steerer for a prostitution house run by a 'Madame'. Here he learns about the perverse past-times of the rich influential whites of American society. During this period, his younger brother Reginald comes to visit him. Reginald had joined the Merchant Marines. On his (Reginald's) second visit to New York Malcolm asks him to stay with him. He also puts him up with a 'small hustle' where Reginald had to lift watches and jewelry from shops. It was a 'safe' hustle, considering that his brother was a novice in this field.
Throughout this phase Sophia kept in touch with Malcolm. Sophia was married to a wealthy man white man in Boston, yet she continued her relationship with Malcolm. According to the author, neither Sophia nor he was in love with each other. For Sophia it was just the fascination of having a physical relationship with a young good-looking black man, while Malcolm found the relationship rather exciting. White well-to-do women like Sophia were like the proverbial 'forbidden fruit' to black men. Malcolm did not love Sophia but the excitement of having a white girl friend made him want to continue the relationship.