Objective: African Americans experience high rates of type 2 diabetes mellitus (T2D). Self-management strategies, such as medication adherence, are key to mitigating negative T2D outcomes. This article addresses a gap in the literature by examining the intersections of drug abuse histories and medication adherence among urban, older African Americans with T2D. Method: In-depth interview data were collected as part of a larger ethnographic study examining the subjective experience of T2D among urban older adults. Two representative focal cases were selected and thematic analysis performed to illustrate how former illicit drug addicts perceive prescription medication usage. Results: Narratives reveal that participants are displeased about having to take prescription drugs and are making lifestyle changes to reduce medication usage and maintain sobriety. Discussion: Previous drug abuse not only complicates medication adherence but is also a significant part of how older African Americans who are former drug users frame their understanding of T2D more broadly.