bootlegging, in the United States, the illegal distribution or production of liquor and other highly taxed goods. First practiced when liquor taxes were high, bootlegging was instrumental in defeating early attempts to regulate the liquor business by taxation. After the appearance of local and state option, those areas that voted to prohibit liquor were supplied with bootlegged liquor. There was also considerable smuggling from foreign countries in order to evade customs duties. In the period of prohibition (1920–33) these activities increased greatly, and by 1930 they were well organized as a large illegitimate industry. Certain areas were dominated by gangs that fought to defend or extend their territory. Infamous gangsters such as Al Capone in Chicago and Legs Diamond in New York City were heavily involved in bootlegging. The retail outlet in the prohibition period was the speakeasy, though a house-to-house delivery system to established customers was also well developed. A high degree of organization also prevailed in international liquor smuggling. The combination of graft and violence accompanying this industry became so intolerable that it was an important factor in the final repeal of prohibition. Bootlegging remains a practice in many areas where prohibition is still in practice. Other highly taxed products may also become a target for bootleggers, e.g., a system of bootlegging untaxed cigarettes into New York City existed in the early 1970s.
See K. Allsop, The Bootleggers (1961, repr. 1970); A. Sinclair, Prohibition: The Era of Excess (1962, repr. 1964); H. Waters, Smugglers of Spirits (1971).