While a great deal of research captures the lived experiences of Black men as they navigate through the criminal legal system and onto reentry, very little research is grounded in how those processes are directly connected to their health. Although some research argues that mass incarceration is a determinant of poor health, there is a lack of qualitative analyses from the perspective of Black men. Black men face distinct pathways that lead them into the criminal legal system, and these same pathways await them upon reentry. This study aims to examine the health implications associated with incarceration and reentry of Black men. While adopting a phenomenological approach alongside interviews, our findings show both race- and gender-specific outcomes for the men in our sample. For example, health and wellness appears to be a significant theme that governs their (in)ability to matriculate society. Moreover, their contact with the criminal legal system appears to exacerbate health concerns and hindrances toward reentry. Other themes include mental health and the role of masculinity. We conclude with implications on policy and future research.