This chapter explores the dynamics of an anti-mafia challenge that took place against the Sicilian Mafia during the 1980s and 1990s, with a focus on the regional capital, Palermo. Exemplar mafia formations were organizations that consolidated themselves before the turn of the twentieth century in Italy, Japan, and the United States, somewhat later in Hong Kong and Taiwan, and – with qualifications – in 1990s’ Russia. During the 1950s and 1960s, the Cold War in full bloom, Italian mafias mobilized votes for the capitalist-friendly, anti-communist, Christian Democratic Party, helped by America’s Cold War mission to contain Soviet influence in Italy, home to Western Europe’s largest Communist Party. During the 1930s, as alcohol prohibition came to an end, mafiosi poured their accumulated capital into supplying and expanding the US market not only for casino gambling, but also for drugs.