In Boston Malcolm had a variety of jobs.For a while he worked as a shoeshiner at a Lindy Hop Nightclub. Malcolm says that he shined the shoes of Duke Ellington and many other notable African-American Musicians. In 1943 Malcolm moved to New York City, During that time he became involved in Drug Dealing, Gambling, Racketeering, Robery, and Steering prostitutes. That year Malcolm and his buddy Malcolm "Shorty" Jarvis both went to jail. Malcolm was sentences to 10 years of prison, but was paroled after 7 years because of his days in school. During prison malcolm earned the nickname of "Satin" because of his hostility towards religion. In prison Malcolm met a self-educated man named John Elton Bembry, who covinvinced him to educate himself. Little developed a great appetite for reading, and much of it was after his prison lights had been turned off.
In 1948 Malcolm's brother Philbert wrote a letter to him about the nation of Islam. Malcolm was not interested until his brother Reginald sent him a letter saying " Malcolm, don't eat anymore pork or don't smoke anymore cigarettes. Ill show you how to get out of prison". That year in february, Malcol was transferred to an experimental prison in Norfolk, Massachusetts a facility that had a much larger library. On august 7, 1952, Malcolm recieved a parole and was released from prison.