This article demonstrates how youth workers in a Dutch city bring together seemingly irreconcilable worlds: the development policies of their organizations and the state on the one hand and the practices, needs, and aspirations of young people on the other. Current policies, like much academic literature on street-level professionals, define youth workers as frontline workers, implementing policies as representatives of their organizations. We approach these workers not as representatives but as brokers. Based on detailed ethnographic research with two youth workers and their interactions with so-called ‘high-risk’ boys, we demonstrate that these workers constantly negotiate boundaries, as they are positioned between the policies and the youth. On a theoretical level, employing the concept of ‘correspondence’, we argue that these brokers bring together different actors, institutions, and resources, yet without fully integrating them and without forfeiting their own autonomous position.