This chapter discusses the roles of women in transnational organized crime. It analyses women’s roles in Italian Mafia organisations, examining some of their significant aspects: from the exclusion of women from powerful places, the concept of paradoxical normality, and the variations of women’s roles over time and within different Mafia organisations to the new frontiers and challenges of the globalisation of criminal markets. The chapter then details two stories of Cosa Nostra women demonstrating, in real life, the complex ambivalence of women’s role in Mafia contexts and the difficulty in predicting their precise evolution, by taking the account of both subjective dimensions and the plurality of variables. In Calabria traces of a woman’s presence can be found in a trial that began in the early years of the 1900s, in which a woman charged with Mafia crimes was presumed to have played a full and responsible part.