The purpose of this exploratory study is to examine the reintegration experiences of Black men who were transferred to adult court and served time in adult prison as teenagers. Twenty-one semi-structured in-depth interviews were conducted with 21 Black men who served prison time when he was a teenager. At present, we know little about the long-term effects of waiver and sentencing practices. Hence, my question and main purpose for this research is this: Does the "ex-convict" label affect the reintegration experiences of Black males after serving time in an adult prison as a youth? I focus on Braithwaite's reintegrative shaming to explore how these men reintegrate and experience shaming. The men reported feeling unprepared to subsist in the workplace. The main reasons for these feelings were because the men spent their youthful years in prison, with very little to no job skills training, leaving them highly unskilled. I also test Braithwaite's (1989) ideas regarding shaming and cultural homogeneity among Black men while exploring how "ex-convicts" re-enter the community through personal interviews in this dissertation. I explored whether Black men experience shaming by their reference or intimate groups (family, partner, and friends), the community and potential employers. I also consider masculinity thesis and Anderson's (1999) "Code of the Streets" thesis, which posits that Black's may have culturally defined perceptions regarding feelings of shame. Findings revealed that there were differences in the shaming felt when the men were in their distinctive environments versus outside of the community. Feelings of shame were felt deeper outside of the community rather than vice versa as Braithwaite (1989) theorize. These findings provide a good test of Braithwaite's (1989) cultural homogeneity thesis. Findings from my research discredit the thesis as the sample reported feeling more shame when they left their communities (distinctive environments) even when cultural homogeneity was high in their distinctive environments.