Born in 1884 or 1886.
Born in Russia, Charles Solomon emigrated at a young age with his parents to New England, eventually settling in Salem, Massachusetts. He was raised there with three brothers. He worked first at a lunch cart or as a short order cook, and was known for his dancing, gaining his first nickname, “Flyboots Charlie,” or perhaps “Sly Boots Charlie.” His first foray into criminal activity was as a professional bondsman, running a major fencing operation and beginning to build his resources.
His diversification is revealed through an extensive rap sheet: his first arrest was with Golda Solomon, likely a relative, for running a house of ill repute, followed by a number of arrests for breaking and entering, receiving stolen goods, gambling and other prostitution related offenses. In all, he served very little time and continued to amass power, based in East Boston.
His longest prison time was delivered in 1922, in a perjury trial related to a narcotics charge decided upon earlier in the year. It was at this first trial that his final nickname was applied, in response to a prosecutor questioning Solomon whether he was the “dope king” of Boston. The prosecution’s case fell apart when a witness mysteriously changed her testimony, and an investigation was launched in response, which revealed that Solomon had paid her some $3,000 to change her testimony. At a second trial, for perjury, he was handed a sentence of 5 years hard labor in federal prison, though he was eventually released on a technicality after only 13 months.
Following his short prison stay, his power continued to grow, especially when he bought into the bootlegging business, arranging for payoff to import booze from across the Atlantic Ocean, while continuing to sell narcotics, flesh, and gambling entertainments, as well as significant ventures in property and fencing. However, his power has drawn both legal and criminal attention, notably in a clash between a lieutenant of Frank Boyle, considered the Irish boss of South Boston, Michael O'Connell, and a long time enemy of Boyle's and ally of Solomon's, a man by the name of James Murray, during O'Connell's stay in Charlestown prison. Long a base of significant power for Solomon, operating through Murray virtually in control of all product moving in and out, O'Connell's efforts led to the direct collapse of Murray's organization, the death of Murray, the loss of several warehouses full of product, and the attention of Boyle's mob, until then unaware of Solomon's growing power. The conflict did not spin out into direct confrontation in the streets, but each group remains warily aware of the other.