Re-entry as a field was developed in response to the criminal justice system’s efforts to counter high recidivism rates where repeat offenders cycle in and out of prison. Consequently, government and non-profit stakeholders have developed social services programming to respond to the needs of those released from prison in ensuring they have the support needed to break free of a lifestyle of continuous crime. Scholars in the field have identified employment as a key factor that discerns whether ex-offenders desist from offending or not. That being said, the field has focused more on how ex-offenders acquire employment and less on how they keep their jobs. The objective of this paper is to explore the latter and in the process, reveal the structures that bar returning citizens from maintaining their positions in the workforce and from re-integrating with society at large. In undertaking this study, I partnered with the Chicago South Side non-profit organization, Teamwork Englewood, to conduct quantitative and qualitative analyses of how their clients have fared since undergoing the process to become hired and work for the industrial plant Dakkota Integrated Systems. I have identified the deindustrialized landscape of Chicago as a primary obstruction to ex-offender clients’ retaining their positions at Dakkota, presenting geographic barriers for clients unable to finance their commutes to such faraway worksites and socioeconomic barriers that relegate ex-offenders to a form of employment with low pay and erratic hours that processes them more so as bodies than as people. In highlighting these barriers, I posit both short-term solutions that would better equip ex-offenders for navigating Chicago’s current landscape and long-term solutions that call for the economic reinforcement of the South Side to ensure both ex-offenders and their communities can heal from historically damaging developments and grow together.