The current study explores the major challenges (in the form of risk factors) that may influence unemployed youths’ involvement in gang and criminal activity in Lagos, Nigeria. A combination of techniques (e.g., oral, in-depth interviews, and questionnaires) were used for the data collection. The computed outcomes establish some of the major conditions (e.g., large families, rural/urban migration, poverty, and police corruption) faced by the vulnerable youths before turning to gang and criminal activity as an alternative opportunity to improve their lot in life. The possible implications of the current findings on risk-focused prevention strategies are discussed.