The essay examines the intricate relationships between labour law and legislation against mafia organized crime infiltration, focusing on the perspective of EU law. Two main areas of interest are analyzed: the first – of a technical-legal nature – concerns the balance between workers’ rights, freedom of enterprise, and the protection of public safety; the second – of an empirical nature – concerns the effectiveness of countermeasures against mafia organized crime and the adequacy of controls on businesses. Drawing upon the findings of the analysis, the essay aims to contribute to a deeper understanding of the challenges posed by the legislation against organized crime and to formulate some possible development in order to guarantee a better balance between the interests at stake.