This chapter outlines a history of Transnational Organized Crime (TOC) in North America and the Caribbean that challenges the validity of some assumptions and the present dominant American-based approach to the control of TOC. The scale of the United States alone made effective prohibition of both alcohol and drugs an impossible dream. American alcohol prohibition was very profitable to its geographical neighbours, in particular to Canada, the Caribbean islands and Mexico. Alcohol trafficking gave the Mafia ‘the opportunity to organize on a national scale, and to gain internal discipline on a national scale’, according to the 1950s Senate investigative committee headed by John McClellan, for example. The process of harmonizing drug control policies began earlier and in many ways prefigured the ‘harmonization’ of organized crime control policies. The American prison gang phenomenon had implications for America’s most pressing present TOC-related concern, the Mexican drug wars, according to an investigation for the Associated Press by Christopher Sherman.