Abstract This thesis explores the desistance promoting potential of professional relationships between male youth workers and young men involved in violence. It adopts a psychosocial methodological and analytic frame to examine a common-sense proposition: that male workers who are colloquially described as Ã¢ÂÂdown with the kidsÃ¢ÂÂ are especially well suited to engage and mentor young men involved in violence. Five intensely observed longitudinal case studies follow the trajectories of young men and their youth workers over six years. Each case utilises different conceptual tools to offer different insights into their relationships, including: the presence of gendered, generational and unconscious dynamics between young men and male workers; how reciprocal identification can lead to male youth workers not seeing how young men neutralise their violent offending; worker reflexivity as a pre-requisite of the youth work role in late modernity and how this can be fractured by the biographical experiences of too-wounded healers; the importance of male workers with resources of street-social and masculine capital creating a third space where they and young men can examine their own intersectional identities, and; how worker self-disclosure can shift doer done-to dynamics within professional relationships and organisations. The thesis concludes that the male worker as mentor and role model discourse generates both assets and potential shortcomings in terms of desistance promotion. Embodying a Ã¢ÂÂdown with the kidsÃ¢ÂÂ worker subjectivity can provide a ready route into youthful, masculine subcultures and a means for male workers to meet their own need for generativity. But without proper training and supervision there is a risk that workers with their own history of offending can be ineffective at best, and at worst descend into professional burn-out. In this sense being down with the kids can lead inadvertently to workers going down with the kids. Reconceptualising youth work relationships incorporating psychodynamic and post structural perspectives (i.e. as psychosocial) offers a way to work through these issues productively and can usefully inform youth work practice and policy.