Formerly incarcerated persons face challenges in obtaining employment and housing upon release, and the literature is consistent in showing themes of social support as a positive influence in obtaining these necessities. These themes are supportive of life-course approaches that suggest social support structures are necessary for desistance from crime. This paper utilizes data from the Enhanced Services for the Hard-to-Employ Center for Employment Opportunities (CEO) in New York City to assess the impact of mentorship on rearrest for members of the program group. The sample includes CEO program participants who were referred to the program by their parole officers and were able to participate in transitional jobs, coaching and development, parenting classes, and post-placement services. Binary logistic regression was used to assess the influence of mentorship on rearrest while controlling for age, marital status, education, prior felony arrests, and housing. Results indicate that mentorship does not influence rearrest. The results do indicate that age and prior felony arrests have influence on rearrest. Suggestions for future research and policy discuss measuring mentorship through participant evaluations of existing and future programs.