Research suggests that the ability to perform traditional masculinity is often challenged by the presence of chronic illness. Specifically, diagnosis with chronic illness has a dramatic impact on men's self-presentation, sexuality and relationships, and shapes the quality of their daily-lived experiences. We examined how older Black men view themselves and their role in society/their community following diagnosis with chronic illness(es), using an in-depth life history narrative interviews with Black men, aged 55 years and over. Data revealed that the presence of chronic illness profoundly impacts the sense of masculinity among these men. Further, result shows that inability to perform masculinity due to chronic illness diagnosis has implication for physical wellbeing, identity and sense of belonging to the community, and overall quality of life. Our findings capture a sense of how older Black men negotiate the incompatibility between chronic illness diagnosis and performance of normative masculinity.