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Recent research, especially at European level, has increased the knowledge about the involvement of organised crime groups in legitimate businesses, and about where and how this infiltration occurs. However, there is still the need for an in-depth understanding of the drivers that move criminal groups to focus on some specific economic activities. Building on the preliminary results of EU co-funded project MORE, this paper aims to explore the vulnerabilities that make certain territories and certain business sectors more exposed to infiltration than others. Through an empirical analysis of about 2,000 companies seized from mafia groups in Italy in the last thirty years, it assesses if the investment choices of mafias mirror the business structure of the territory, or if, on the contrary, are driven by other utilities and facilitated by vulnerabilities at regulatory level and in the socio-economic fabric. As a result, the paper offers also some new perspectives on the historical evolution of the ‘mafia-entrepreneur’ in the last thirty years.