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This chapter examines the rise of the Italian Mafia from the perspective of culture and politics. Culture has had a significant effect on the rise of the Mafia in Southern Italy, where traditional and collective values reflective of an agricultural economy tend to valorise cultural attributes such as honour and trust. Apart from culture, politics has also had a major influence in the development of the Italian Mafia. Governments used different preventive measures against the Italian Mafia but they could not manage to eradicate the Mafia from the country completely. Although the Italian Mafia has already been examined through culture and politics by various scholars, this chapter firstly introduces the concept of ‘double oppression’ as a new paradigm from the angle of the failure of individualism in Southern Italy, as well as the concept of ‘ad hoc and indecisive policies’ as the outcome of an absence of strong, transparent and uncorrupted governments in the fight against the Italian Mafia. The chapter argues that Italian Mafia has become stronger and undefeatable because of two major facts: a failure of individualism and a lack of state determination and decisiveness.