This article analyzes ethnographic data collected from a gang intervention program to examine how former gang members use their experience to influence youth still involved in gang life. I argue that the interventionists possess a ‘street liminality’ that is constructed by their experiences living along the margins of both the street and conventional society. This street liminality enables the interventionists to exploit the connections they have to these two social realms, making resources accessible to barrio youth and helping them navigate criminalizing social institutions. However, they must constantly balance the interests of the youth they serve against those of the civil leaders they depend on for funding to ensure that they do not facilitate these youth’s criminalization. By illustrating the processes of how street liminalty is embodied, used, and negotiated, this article discusses how we can expand our understanding of liminality and recognize its potential for working around hierarchical boundaries.