The literature on mentorship centralizes formal mentoring programs with hired and trained staff and volunteers to work with at-promise youth of color at school- or community-based sites such as Big Brothers Big Sisters or smaller localized programs; however, these programs are not always available in rural areas. This multiple case study explores the phenomenon of naturally-occurring mentorships among Latine, gang-affiliated youth to evaluate what mentorship is and how mentoring relationships are cultivated and sustained. The research draws on fieldnotes, 300 hours of observations, eight three-phase semi-structured interviews with mentoring pairs, and written and pictorial evidence of the socio-political climate of the community confirmed through 20 semi-structured interviews with community leaders and elders. The study's findings apply elements of aspirational, navigational, and resilient cultural wealth according to Yosso's (2005) Community Cultural Wealth framework and were member-checked by mentoring participants. The findings suggest that a mentor can be an individual holding familial space in the mentee's life; while the act of mentorship entails listening attentively, providing advice based on personal experiences, supporting the mentee in "getting out" of their hometown, and speaking one's truth even if it is difficult to hear.