South Africa wasSouth Africa under apartheidApartheid rule from 1948 to 1994, which allowed for the unequal development of different racial groups in the country. In response to this inequity, those who have been disadvantaged have found alternative ways to cope with the deprivation they experience. One such pathway is young boys joining street gangs. This chapter focuses on the findings of an ethnographic study that aimed to gain deeper insight into the experiences of Black African and Coloured boys (10–16 years old), who awaited trial in a Child and Youth Care CentreChild and Youth Care Centres (CYCC) located in the Western Cape, South AfricaSouth Africa. The research methods employed individual interviews, focus group discussions, and participant observation, with the young boys as the key participants. Based on the collected data, the boys’ experiences and narratives revealed how intergenerational poverty shaped their lives, leading them to seek social, economic, and physical protection by joining street gangs, which often resulted in criminal and violent experiences. To mitigate this pathway for young boys, this chapter proposes that Haines and Case’sHaines and case ChildChildren First philosophy and approach be introduced and adopted as a social interventionSocial intervention to support and strengthen the ethos and objectives of the ChildChildren Justice Act (No. 75 of 2008) in South AfricaSouth Africa.