Problems related to distrust of police, including aggressive and prejudicial police behavior, continue to raise concerns. Using a procedural justice model, the present study examines perceptions of trust or the lack thereof among a subpopulation of young disadvantaged minority youth that routinely come in contact with the police: drug-dealing gang members. In this article, we examine 253 qualitative in-depth interviews comprised primarily of African American and Latino male and female drug-involved gang members, utilizing a comparative analysis, to examine how participants discuss interactions with law enforcement and describe situations where they trust the police or situations where they do not. The findings suggest that the context in which they were stopped operates as a primary differentiating component that shapes their perceptions of trust in the motivations behind police engagement. When stopped by the police for "justifiable" reasons, the participants expressed a trust in the motivations that necessitated the encounter. However, when stopped for reasons, which appeared as unreasonable, our participants voiced a strong sense of distrust in the motivations of the police. These findings suggest that procedural justice scholars should consider the extent to which the type or context of the encounter with the police plays an important role in influencing feelings of trust.