Culture and tradition are part of the macrosystem of ideas and beliefs that have a dramatic effect on children and families. One aspect of culture is gender beliefs, values and roles. Feminist analysis has explored the incorporation of gender in a wide range of structures, challenging gender bias and advocating reform of a range of laws, structural systems, and social practices. Masculinities analysis, an outgrowth of feminist analysis that focuses on men as gendered subjects, provides a perspective to consider those areas in which men are disproportionately present either in positions of power and privilege, or in positions of disadvantage. The juvenile justice system is a place where boys are the primarily objects of the system. Yet it is a system that rarely considers boys as gendered subjects. This article examines the perspective that masculinities scholarship would bring to evaluating and reforming the juvenile justice system.