Depression can be a pathway to older men's suicide, yet the mechanisms by which this can occur are poorly understood. A qualitative study of 22 older men who self-identified or were formally diagnosed with depression was conducted to describe the connections between masculinity, depression, and suicide. Analyses of individual interviews revealed that cumulative losses around social bonds were central to older men's depression, apathy for living, and thoughts about suicide. Prominent were men's self-assessments of failing to fulfill breadwinner roles, judgments that led participants to ruminate on their shortcomings amid recognizing their older age as limiting opportunities for redemption. Stigma featured as a barrier for men acting on their suicidal thoughts, and guilt about the pain their suicide would evoke on family and friends was a strong deterrent for men's self-harm. Overall, participants' alignment to masculine ideals influenced both the connectedness and detachment between older men's depression and suicide.