Sociology has a rich tradition studying ‘elite’ and ‘street’ social spaces, but rarely considers spaces between these fields and the social actors within them. This article fills that gap by examining the life stories of affluent Oslo youth engaged in illegal drug dealing. Participants had access to economic, social, and cultural capital in both elite and street social space. Making money in legitimate and illegitimate ways kept participants relatively marginal in both spaces. Having social networks among street-oriented peers and among elites facilitated drug dealing but also allowed them an exit from drug crimes when needed. They were educated and often employed, but also had high levels of drug and street cultural competence. This left them relatively estranged from their affluent background milieu leading to persistence in drug dealing. I argue that illegal drug markets among the affluent can be viewed as an in-between social space, that ‘elite’ or ‘street’ youth are likely best conceptualized as existing on a sociocultural spectrum between fields and provide a Bourdieusian framework to study social actors who stand between fields and the impact this may have on their lives.