The iconic figure of Al Capone is arguably the most prominent figure of organised crime. Both biographers and scholars have analysed his life and behaviour. Hollywood has immortalised his character in film. Today, the name Capone remains synonymous with the word gangster. Although Capone owned businesses of a legitimate nature, illicit ventures and the spectre of the gangster-entrepreneur define his practice of entrepreneurship. In an attempt to understand Capone as an entrepreneur, this paper explores his entrepreneurial behaviour within an analysis of his resource profile, his Italian-American culture and the social context of the USA in the early 20th century.