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Many scholars have argued that organized crime is a topic beyond objective measure. It is difficult to conduct reliable empirical research on an entity concealed in the criminal underworld. Because it is difficult to gain access to the internal dynamics of a criminal organization, social scientists are forced to rely on accounts supplied by police, judicial authorities, and the media, and on reports from key witnesses. Gaining access to police files and interviewing witnesses, however, is far from a simple task. This article identifies challenges of conducting organized crime research and illustrates how qualitative approaches such as life narrative, ethnography, and case study can improve our understanding of organized crime. The discussion on the strengths and weaknesses of qualitative designs in understanding the nature of organized crime is based on the author’s own qualitative research, including in-depth interviews with offenders inside and outside of prisons, as well as on systematic review of the academic literature on the topic.