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Crime is generally understood as a form of deviance. But recent historical examples from Eastern Europe put this understanding into question. Adopting a “Global East” perspective of Eastern Europe as a specific and distinctive site of knowledge production, this paper investigates the particular circumstances in which behaviour deemed criminal by the legal code is broadly understood as socially acceptable and even tolerated by the security forces. Drawing on qualitative biographical research with individuals who engaged in informal entrepreneurial activities under the socialist command economy in Czechoslovakia, the paper demonstrates how individuals engaging in economic criminality construct their behaviour as justified and to what extent they apply similar justifications to their entrepreneurial activities after 1990, when private enterprise became fully legalized after the collapse of the communist regime. Such an enquiry into subjective understandings of legality and criminality poses the question also to other geographical and historical contexts whether crime is a useful category for investigating economic social practice in situations of social and political change.