In the earlier part of this century two men, Calogero Vizzini and Genco Russo, were widely viewed as being, one in succession to the other, supreme head of the Sicilian mafia. The authors of these profiles differ in their assessment of this power, but agree that each can be considered as a representative figure of the mafia in the political-social conditions of their times. Their biographies are indispensable to an understanding of the operation of the rural mafia, before its transformation into an urban phenomenon. This chapter presents two portraits representing the generation of mafia who had no knowledge of the traditional rural mafia and who lived through its transition from urban phenomenon to international drug-dealing gangsterism.