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Studies examining the impact of criminal history and incarceration on effective reintegration following release have focused almost exclusively on traditional offenders, leaving a substantial gap in our understanding of the post-incarceration experiences of white-collar offenders. It may be the case that in some instances a white-collar offender’s education, social and economic capital, and personal and professional networks allow them to navigate the post-prison environment relatively unscathed. However, it may also be the case that the nature and quality of pre-incarceration relationships substantially affects the offender’s chances for successful reintegration following incarceration. This paper relies upon data from a recently completed study of formerly incarcerated white-collar offenders to investigate the impact and influence of white-collar offenders’ personal and professional relationships on their perceptions of successful post-incarceration reintegration. Data were collected through a series of semi-structured interviews with formerly incarcerated individuals as a way to chronicle the successes, failures, and on-going struggles faced by this ‘privileged class’ of offenders. Several important themes emerged highlighting the importance of an offender’s support networks as pre- and post-incarceration factors that substantively influence white-collar offenders’ quality of life following incarceration.