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In this criminological study we have combined ethnographic fieldwork observations with twelve in-depth interviews with Swedish street gang leaders and twelve associate gang members to understand the driving forces behind street gang leadership and gang membership by delineating the multiple themes of the subjects’ narratives. A descriptive and interpretive analysis of the data suggested four ideal-types, each with specific goals, aspirations, and motives. These were in accord with a limited, though diverse literature on gang leadership that has primarily emerged in the United States. The analysis, however, does not necessarily support the claim that U.S.-style intergenerational, institutionalized gangs exist in Sweden; simply that there are similar gang leadership styles and motivations in these different contexts. In terms of policy, the analysis contains important lessons for agencies involved in social control efforts against street gangs and similar subcultures by focusing on the heterogeneous roles and influences of gang hierarchies. Further, the analysis reiterates the need for a more nuanced understanding of street gangs and the structured agency of members within their own narrative accounts. In terms of research, these findings suggest a need for further in-depth, holistic studies to create a more empirically grounded gang leader typology.