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The establishment of cooperative relationships with political actors is crucial for organized criminal groups that seek to expand their influence beyond the underworld. This has been particularly evident in Italy, where mafias have persistently wielded power over the political sphere, refining their strategies to establish successful linkages with government officials over time. This study seeks to analyze and categorize the patterns of interaction between political representatives and criminal organizations in Italy, with the aim of identifying the defining characteristics of the actors involved and the strategies used to reach cooperative agreements. To achieve this, content analysis of Italian judicial documents was undertaken, so as to identify the case studies, conditions, and characteristics of the political-criminal nexus. Results highlight the relevance of both the structure of the criminal syndicates and the existing political system in shaping the type and objectives of these cooperative relationships. Understanding the dynamics underpinning political-criminal interactions can be particularly useful in developing effective policies to counter and prevent the misuse of public resources.