Previous work suggests that control and suffering are related to one another. Although it would be expected that within cultures which emphasize the importance of masculinity, as well as personal control, there would be greater suffering among individuals who lose their sense of masculinity or control, how these constructs relate to each other and are individually negotiated has been largely understudied. This paper takes a case study approach to further exploring how the constructs of control, masculinity, and suffering are related in the lived experience of an older European American man, Mr. Gregor. Analysis of this case shows that masculinity is related to control and that these constructs act as themes which interact over Mr. Gregor's lifetime in a variety of ways. The level of control maintained by Mr. Gregor in different aspects of his life affects his sense of suffering. In some instances his sense of masculinity helps to protect Mr. Gregor against suffering; in others, it contributes to his suffering. These findings support the notion that there are culturally dependent possibilities for how control and masculinity are related.