In 1945, Malcolm Little returned to Boston from New York City, a petty criminal with an expensive drug habit and a white girlfriend. He and his friend, Malcolm “Shorty” Jarvis, would case houses and apartments, steal their valuables, and sell them to pawnshops for money. In 1946, the men were arrested and convicted on charges of larceny, breaking and entering, and carrying a weapon. In February of 1946, Malcolm Little and Malcolm Jarvis were sentenced to eight to ten years in prison. It was the culmination of several years of small-time criminal behavior for Malcolm, then twenty years old, and marked the beginning of his transformation into a radical politician and civil rights leader.

Malcolm began serving his sentence at Charlestown State Prison in Boston. In 1947, Malcolm converted to the Nation of Islam at the urging of his brother Reginald. Malcolm was transferred in 1948 to Norfolk Prison Colony, where he began to take advantage of the extensive library to educate himself. Malcolm served six years of the ten year sentence, and was paroled in 1952. He dropped his surname “Little”—which he considered a slave name—and took the initial “X” to signify his true, lost name.