Recent times have seen a steady growth in studies about gangs and their membersin prison. Despite the increased interest on gangs in prison, there is much to learn about their members. Specifically, emerging research indicates that gang members disengage from their gangs while in prison, however, explanations for why members leave have been limited to individual level factors. Little is known about how the gang context influences the process of disengagement in prisons. Further, despite disengaging from their gangs, former members continue to be at a higher risk for recidivism upon release, when compared to non-gang members. The current body of literature fails to explicate the mechanisms that increase a former member’s risk for recidivism. Accordingly, this dissertation seeks to advance the literature by asking three primary questions: 1) Does gang organization matter for disengagement from gangs in prison?; 2) Do reentry experiences differ by gang membership status—current, former and non-gang member?; 3) Do reentry experiences impact reintegration outcomes? Data from the LoneStar Project—a multi-wave study that explores thetrajectories, associations and reentry among 802 gang and non-gang involved inmates released from Texas prisons—are used. Regression models are estimated to assess the effects of the gang organization on disengagement and to compare the reentry and reintegration experiences of current, former and non-gang members. The results indicate that gang organization is important for disengagement in prison. Further, upon release, former gang members show no differences in their reentry and reintegration experiences when compared to non-gang members. Former members, however, show higher levels of motivation for change and better mental health 1 month after release, when compared to current members. Additionally, current gang members are found to have the lowest levels of psychological reintegration 9 months after release. These differences are found to be mediated by levels of motivation for change and mental health at 1 month after release. The findings are discussed in light of their implications for continued theoretical development, future empirical research and the creation of public policy concerning gang members