In late 1945, Little returned to Boston. With a group of associates, he began a series of elaborate burglaries targeting the residences of wealthy white families. On January 12, 1946, Little was arrested for burglary while trying to pick up a stolen watch he had left for repairs at a jewelry shop. The shop owner called the police because the watch seemed too expensive for the average Roxbury resident. Little told the police that he had a gun on his person and surrendered so the police would treat him more leniently.
Two days later, Little was indicted for carrying firearms. On January 16, he was charged with larceny and breaking and entering, and eventually sentenced to eight to ten years in Massachusetts State Prison.