alcolm moved to Detroit to live with his half sister, Ella in 1941. By the time Malcolm arrived in Detroit it appeared he had made up his mind about school; he wanted no part of school and the indignity that came with it. Like any other young black man he wanted money and desired a life without the control or influence of the white establishment. But there was no escaping the establishment and he ran afoul of the law several times. He worked variously as a shoeshine boy, a pimp, drug courier, and was a petty thief. He fancied the good clothes and attires of his time, and the "zoot suit" became his preferred outfit. His hair was transformed when he conked it with a mixture of lye, potatoes and eggs. Conking was a lifetime desire of every young man of his time and Malcolm was not left out. He later came to see conk as demeaning for a black man and he eventually disdained it.

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Malcolm X lived the life of a hustler and thrived very well in it, eventually finding a way to avoid being drafted into the Army; Malcolm X was determined never to allow himself to be used to fight a war he considered "the white man's war." He honoured the invitation to attend a review but acted like a madman who needed help when he got there. His acting was so good he got a letter in the mail weeks later considering him unfit to recruit in the army. An official report released by the FBI later offered the following assessment: "The subject was found mentally disqualified for military service for the following reasons: psychopathic personality inadequate, sexual perversion, psychiatric rejection."

Malcolm X lived his life on the street and struggled to survive. Though he worked here and there, it was hustling that became his preferred career of choice. Alex Haley in the The Autobiography of Malcolm X described a young man who had ceased "seeking legitimate work and had graduated from small-time street hustling into burglary, armed robbery, and prostitution, in order to pay for what was becoming a regular drug habit." Though Professor Marable disputed these facts in this new biography, he nonetheless acknowledged that between 1944 and 1946 Malcolm X was "struggling to survive. His sporadic work at Jimmy's Chicken Shack had dried up, leaving him to find other ways to scrape by."

Malcolm X moved back his sister Ella Collins's house in Boston. His stay with Ella led to an arrest as Malcolm pawned another sister, Grace's treasured fur coat for $5 in order to get some money to feed his drug habit. Elder sister Ella was so outraged she called the police. Malcolm was arrested and sent to jail. He was eventually given a three month suspended sentence with a year probation, which was his first "offence to result in arrest and conviction," according to Marable. Malcolm became known as Detroit Red the hustler and he was just nineteen years old at the time. Malcolm then went to Lansing and worked at the East Lansing's Coral Gables bar and later as a busboy at Lansing's Mayfair Ballroom. But these jobs, according to Marable, were "opportunities for petty theft" as he robbed a friend, Douglas Haynes, at gun point on the road to Detroit. Malcolm was arrested and charged with grand larceny. He was eventually released on bail.

However, it was in Boston that Malcolm X established a crew, a gang of petty thieves that included his friend, Shorty Jarvis, X's girlfriend, Bea Caragulian, Bea's sister Joyce Caragulian, Francis "Sonny" Brown and Kora Marderosian. The crew targeted and robbed homes in affluent neighbourhoods around Boston. They will steal jewelries, watches, pendants, silverwares, fur coats and the like. The gang did very well on their hustling trips but was finally caught by police. This landed Malcolm and Shorty in jail. The two young men were sentenced to four concurrent jail terms of between eight and ten years. What hurt Malcolm the most was the fact that the presiding judge conceded to the plot of the prosecution which presented the two white girls, Bea and her sister Joyce as "innocent victims of Malcolm's vicious criminal enterprise," agreeing to Bea's plea that she and her sister were coerced. Bea served only eight months of her five-year sentence. Malcolm was infuriated and held on to the conviction that he was given a long prison sentence because of his involvement with a white woman. He ended up at the Charlestown State Prison along with Shorty in January 1946.

A mug shot of Malcolm X during his hustler years when he was known as Detroit Red

It was at Charlestown that Malcolm X met the man that will influence his life for good. John Elton Bembry was a burglar, but Bembry was a near intellectual and a brilliant mind whose range of interests cover a wide spectrum of subjects and topics. Malcolm learnt a lot from Bembry and took to books like his life depended on them. He then enrolled in correspondence courses and embraced the prison library. At Norfork Prison Colony where he was later transferred to, Malcolm was very active in the debate club and engaged in weekly contests on a variety of issues, "Right there, in the prison, debating, speaking to a crowd, was as exhilarating to me as the discovery of knowledge through reading, " he observed, adding: "Standing up there, the faces looking up at me, things in my head coming out of my mouth, while my brain searched for the next best thing to follow what I was saying, and if I could sway them to my side by handling it right, then I had won the debate - once my feet got wet, I was gone on debating." Malcolm X's transfer to the Massachusetts's Norfolk Prison Colony gave him access to more books and a bigger and better library which helped him to further his self-education. By this time education had become his major goal in his life. Malcolm X was later to debate and floor university scholars and intellectuals in the universities and media houses in the United State.

Malcolm X addressed a largely white audience at the University of Hartford in Connecticut.